Document:

Seventh Supplemental Indenture, dated as of February 9, 2012

 Exhibit 4.3 
 EXECUTION COPY 
  
  

 
 SEVENTH SUPPLEMENTAL INDENTURE

 Dated as of February 9, 2012 
 Supplementing that Certain 
 INDENTURE 

Dated as of November 21, 2011 
  

 
 Among

 ARISTOTLE HOLDING, INC., 
 THE GUARANTORS PARTY HERETO 
 and 

WELLS FARGO BANK, NATIONAL ASSOCIATION, 
 as Trustee 
  

 
 3.900% SENIOR
NOTES DUE 2022 
  
  

 

 This Seventh Supplemental Indenture, dated as of February 9, 2012 (the “Seventh
Supplemental Indenture”), among Aristotle Holding, Inc., a corporation organized and existing under the laws of the State of Delaware, having its principal office at One Express Way, St. Louis, Missouri (herein called the
“Company”), the Guarantors party hereto and Wells Fargo Bank, National Association, a national banking association, as Trustee hereunder (herein called the “Trustee”), supplements that certain Indenture, dated as of
November 21, 2011, among the Company, the Guarantors and the Trustee (the “Base Indenture” and, together with this Seventh Supplemental Indenture, the “Indenture”). 

RECITALS OF THE COMPANY 
 A. The Company, the Guarantors and the Trustee have entered into the Base Indenture, which provides for the issuance from time to time of the Company’s unsecured debentures, notes, or other evidences
of indebtedness to be issued in one or more series as provided for in the Base Indenture. 
 B. The Base Indenture provides that
the Securities of each series shall be in substantially the form set forth in the Base Indenture, or in such other form as may be established by or pursuant to a Board Resolution and set forth in an Officers’ Certificate or in one or more
supplemental indentures thereto, in each case with such appropriate insertions, omissions, substitutions, and other variations as are required or permitted by the Indenture, and may have notations, legends or endorsements required by law, stock
exchange or automated quotation system on which the Securities may be listed, quoted or designated for issuance, agreements to which the Company is subject, if any, or usage or as may, consistent therewith, be determined by the officers executing
such Securities, as evidenced by their execution thereof. 
 C. The Company and the Trustee have agreed that the Company shall
issue and deliver, and the Trustee shall authenticate, a new series of Securities to be known as the “3.900% Senior Notes due 2022” pursuant to the terms of this Seventh Supplemental Indenture and substantially in the form set forth in
Appendix A hereto (together with the Exhibits thereto, the “Appendix”), in each case with such appropriate insertions, omissions, substitutions, and other variations as are required or permitted by the Indenture, and with such
notations, legends or endorsements required by law, stock exchange or automated quotation system on which the Securities may be listed, quoted or designated for issuance, agreements to which the Company is subject, if any, or usage or as may,
consistent herewith, be determined by the officers executing such Securities, as evidenced by their execution of such Securities. 

 ARTICLE I 
 Issuance of Securities 
 SECTION 1.1. Issuance of Securities; Principal
Amount; Maturity; Title. 
 (1) On February 9, 2012, the Company shall issue and deliver to the Trustee, and the Trustee
shall authenticate, the Initial Securities substantially in the form set forth in the Appendix, in each case with such appropriate insertions, omissions, substitutions and other variations as are required or permitted by the Indenture, and with such
notations, legends or endorsements required by law, stock exchange or automated quotation system on which the Securities may be listed, quoted or designated for issuance, agreements to which the Company is subject, if any, or usage or as may,
consistent herewith, be determined by the officers executing such Securities, as evidenced by their execution of such Securities. 
 (2) Pursuant to the terms hereof and Section 3.1 of the Base Indenture, the Company hereby creates a series of Securities designated as the “3.900% Senior Notes due 2022” of the Company
(including both the Initial Securities and any Additional Securities (as defined below), the “Securities”), which Securities shall be deemed “Securities” for all purposes under the Indenture. 

(3) The Initial Securities to be issued pursuant to this Seventh Supplemental Indenture shall be issued in the aggregate principal amount
of $1,000,000,000 and shall mature on February 15, 2022 unless the Securities are redeemed prior to that date as described in Sections 4.1 or 4.2 of this Seventh Supplemental Indenture. The aggregate principal amount of Initial Securities
Outstanding at any time may not exceed $1,000,000,000, except for Securities issued, authenticated and delivered upon registration of transfer of, or in exchange for, or in lieu of, other Securities pursuant to Sections 3.4, 3.5, 3.6, 9.6 or 11.7 of
the Base Indenture and except for any Securities which, pursuant to Section 3.3 of the Base Indenture, are deemed never to have been authenticated and delivered; provided that the Company may without the consent of the Holders, issue
additional Securities hereunder as part of the same series and on the same terms and conditions (except for the issue date, issue price and, in some cases, the first Interest Payment Date) (and having the same Guarantors) as the Initial Securities
(“Additional Securities”). 
 (4) The Securities shall be issued only in fully registered form without coupons
in minimum denominations of $2,000 and any integral multiple of $1,000. 
 SECTION 1.2. Interest. 

(1) Interest on a Security will accrue at the per annum rate of 3.900% (the “Security Interest Rate”), from and including
the date specified on the face of such Security until the principal thereof is paid, deemed paid, or made available for payment and, in each case, will be paid on the basis of a 360-day year comprised of twelve 30-day months. 

 (2) The Company shall pay interest on the Securities semi-annually in arrears on
February 15 and August 15 of each year (each, an “Interest Payment Date”), commencing August 15, 2012. 
 (3) Interest shall be paid on each Interest Payment Date to the registered Holders of the Securities after the close of business on the Regular Record Date. 

(4) The Place of Payment for this Security shall be the corporate trust office of the Trustee at 625 Marquette Avenue, 11th Floor,
Minneapolis, Minnesota 55479. Notwithstanding the foregoing, (i) payments in respect of the Securities represented by a Global Security (including principal, premium and interest) will be made by wire transfer of immediately available funds to
the accounts specified by the Depository and (ii) the Company will make all payments in respect of a Definitive Security (including principal, premium and interest) by mailing a check to the registered address of each Holder thereof as such
address appears in the Security Register; provided, however, that payments on a Definitive Security will be made by wire transfer to a U.S. dollar account maintained by the payee with a bank in the United States if such Holder elects
payment by wire transfer by giving written notice to the Trustee or the Paying Agent to such effect designating such account no later than 30 days immediately preceding the relevant due date for payment (or such other date as the Trustee may accept
in its discretion). 
 (5) Neither the Company nor the Trustee shall impose any service charge for any transfer or exchange of a
Security. However, the Company may ask Holders of the Securities to pay any taxes or other governmental charges in connection with a transfer or exchange of Securities. 
 (6) If any Interest Payment Date, Maturity Date or Redemption Date falls on a day that is not a Business Day in the City of New York, the Company will make the required payment of principal, premium, if
any, and/or interest on the next succeeding Business Day as if it were made on the date payment was due, and no interest will accrue on the amount so payable for the period from and after that Interest Payment Date, the Maturity Date or earlier
Redemption Date, as the case may be, to such next succeeding Business Day. 
 SECTION 1.3. Additional Interest.

 The Company is party to a Registration Rights Agreement, dated as of February 9, 2012, among the Company, the Guarantors
and the representatives of the Initial Purchasers named therein, pursuant to which it is obligated to pay additional interest on the Securities upon the occurrence of certain events specified in the Registration Rights Agreement. 

Subject to the provisions of the Registration Rights Agreement, if a Registration Default (as defined in the Registration Rights
Agreement) occurs, additional interest will accrue on this Security from and including the date on which such Registration Default occurs to but excluding the date on which all such Registration

 
Defaults have been cured or the Securities cease to be Transfer Restricted Securities (as defined in the Registration Rights Agreement), whichever is earlier, at a rate of 0.25% per annum
for the first 90-day period immediately following the occurrence of a Registration Default, and such rate will increase by 0.25% per annum on the 91st day following the occurrence of such Registration Default (provided that the maximum
additional interest rate during the initial 90-day period shall be 0.25% per annum and the maximum additional interest rate thereafter shall be 0.50% per annum, in each case regardless of the number of Registration Defaults that have
occurred and are continuing). The Company will pay such additional interest on regular Interest Payment Dates. 
 SECTION 1.4.
Relationship with Base Indenture. 
 The terms and provisions contained in the Base Indenture will constitute, and are
hereby expressly made, a part of this Seventh Supplemental Indenture. However, to the extent any provision of the Base Indenture conflicts with the express provisions of this Seventh Supplemental Indenture, the provisions of this Seventh
Supplemental Indenture will govern and be controlling; provided, however, that the forms and provisions of this Seventh Supplemental Indenture modify and amend the terms of the Base Indenture only with respect to the Securities.

 ARTICLE II 
 Definitions and Other Provisions of General Application 
 SECTION 2.1.
Definitions. 
 The terms defined in this Section 2.1 (except as herein otherwise expressly provided or unless the
context of this Seventh Supplemental Indenture otherwise requires) for all purposes of this Seventh Supplemental Indenture and of any indenture supplemental hereto have the respective meanings specified in this Section 2.1. All other terms used
in this Seventh Supplemental Indenture that are defined in the Base Indenture or the Trust Indenture Act, either directly or by reference therein (except as herein otherwise expressly provided or unless the context of this Seventh Supplemental
Indenture otherwise requires), have the respective meanings assigned to such terms in the Base Indenture or the Trust Indenture Act, as the case may be, as in force at the date of this Seventh Supplemental Indenture as originally executed;
provided that any term that is defined in both the Base Indenture and this Seventh Supplemental Indenture shall have the meaning assigned to such term in this Seventh Supplemental Indenture. 

“Additional Securities” has the meaning specified in Section 1.1(3). 

“Appendix” has the meaning specified in the recitals to this Seventh Supplemental Indenture. 

“Comparable Treasury Issue” means the United States Treasury security or securities selected by an Independent
Investment Banker as having an actual or interpolated maturity comparable to the remaining term of the Securities that would be utilized, at the time of selection and in accordance with customary financial practice, in pricing new issues of
corporate debt securities of a comparable maturity to the remaining term of the Securities. 

 “Comparable Treasury Price” means with respect to any Redemption Date:
(i) the average of five Reference Treasury Dealer Quotations for the Redemption Date, after excluding the highest and lowest such Reference Treasury Dealer Quotations, or (ii) if the Trustee obtains fewer than five Reference Treasury
Dealer Quotations, the average of all Reference Treasury Dealer Quotations for the Redemption Date so obtained. 

“Definitive Security” has the meaning specified in Section 1.1 of the Appendix. 

“Exchange Securities” has the meaning specified in Section 1.1 of the Appendix. 

“Independent Investment Banker” means one of the Reference Treasury Dealers appointed by the Trustee after consultation
with the Company. 
 “Initial Purchaser” has the meaning specified in Section 1.1 of the Appendix.

 “Initial Securities” means Securities in an aggregate principal amount of up to $1,000,000,000 initially
issued under this Seventh Supplemental Indenture in accordance with Section 1.1(3). 
 “Interest Payment
Date” has the meaning specified in Section 1.2(2). 
 “Maturity Date” means February 15,
2022. 
 “Mergers” means the merger of Aristotle Merger Sub, Inc., a Delaware corporation and Wholly Owned
Subsidiary of the Company, with and into Express Scripts, and the merger of Plato Merger Sub, Inc., a Delaware corporation and Wholly Owned Subsidiary of the Company, with and into Medco pursuant to the Merger Agreement. 

“Private Exchange Securities” has the meaning specified in Section 1.1 of the Appendix. 

“Reference Treasury Dealer” means each of Citigroup Global Markets Inc. and Credit Suisse Securities (USA) LLC (in each
case, or their Affiliates) and three other primary United States government securities dealers selected by the Company, and each of their respective successors; provided that if any of the aforementioned Reference Treasury Dealers resigns,
then the respective successor will be a primary United States government securities dealer in The City of New York selected by the Company. 
 “Reference Treasury Dealer Quotations” means, with respect to each Reference Treasury Dealer and any Redemption Date, the average, as determined by the

 
Trustee, of the bid and asked prices for the Comparable Treasury Issue, expressed in each case as a percentage of its principal amount, quoted in writing to the Trustee by such Reference Treasury
Dealer at approximately 3:30 p.m., New York City time, on the third Business Day preceding such Redemption Date. 

“Registration Rights Agreement” has the meaning set forth in Section 1.1 of the Appendix. 

“Regular Record Date” for interest payable in respect of any Security on any Interest Payment Date means the day that is
15 days prior to the relevant Interest Payment Date (whether or not a Business Day). 
 “Security Interest
Rate” has the meaning specified in Section 1.2(1). 
 “Securities” has the meaning specified in
Section 1.1(2). 
 “Special Mandatory Redemption Date” means the earlier to occur of (i) the 20th day
(or if such day is not a Business Day, the first Business Day thereafter) following the Special Mandatory Redemption Triggering Date, if the Mergers have not been completed on or prior to the Special Mandatory Redemption Triggering Date, or
(ii) the 30th day (or if such day is not a Business Day, the first Business Day thereafter) following the termination of the Merger Agreement for any reason. 
 “Special Mandatory Redemption Notice” has the meaning set forth in Section 4.3 hereto. 
 “Special Mandatory Redemption Price” has the meaning set forth in Section 4.2 hereto. 
 “Special Mandatory Redemption Triggering Date” means April 20, 2012; provided that such date may be extended by the Company on one or more occasions to a date not later than
July 20, 2012, in the event the conditions set forth in Sections 6.1(c), 6.1(e) or 6.2(d) of the Merger Agreement have not been satisfied or waived by the fifth Business Day (as defined in the Merger Agreement) prior to April 20, 2012;
provided, further, that such extended date may be further extended by the Company on one or more occasions to a date not later than October 22, 2012, in the event that the conditions set forth in Sections 6.1(c), 6.1(e) or 6.2(d)
of the Merger Agreement have not been satisfied or waived by the fifth Business Day (as defined in the Merger Agreement) prior to the initially extended date; provided, however, that, in any case, (x) the Special Mandatory
Redemption Triggering Date shall only be extended if and when the Outside Date (as defined in the Merger Agreement) is extended pursuant to Section 7.1(b)(ii) of the Merger Agreement, and the Special Mandatory Redemption Triggering Date, as so
extended, shall be the same date as the Outside Date, as so extended, and (y) if the Special Mandatory Redemption Triggering Date is extended in accordance with the foregoing, the term “Special Mandatory Redemption Triggering Date”
shall mean such date as so extended. 

 “Treasury Rate” means, with respect to any Redemption Date, the rate per
year equal to the semiannual equivalent yield to maturity or interpolated (on a day count basis) of the Comparable Treasury Issue, assuming a price for the Comparable Treasury Issue (expressed as a percentage of its principal amount) equal to the
Comparable Treasury Price for such Redemption Date. 
 ARTICLE III 

Security Forms 
 SECTION 3.1. Form Generally. 
 (1) Provisions relating to the Initial
Securities, the Exchange Securities and the Private Exchange Securities are set forth in the Appendix, which is hereby incorporated in, and expressly made part of, this Indenture. The Initial Securities and the Trustee’s certificate of
authentication with respect thereto shall be substantially in the form of Exhibit 1 to the Appendix. The Exchange Securities and the Private Exchange Securities and the Trustee’s certificate of authentication with respect thereto shall be
substantially in the form of Exhibit 2 to the Appendix. The Securities may have notations, legends or endorsements required by law, stock exchange or automated quotation system on which the Securities may be listed, quoted or designated for
issuance, agreements to which the Company is subject, if any, or usage or as may, consistent herewith, be determined by the officers executing such Securities (execution thereof to be conclusive evidence of such approval). Each Security shall be in
fully registered form and shall be dated the date of its authentication. The terms of the Securities set forth in the Appendix are part of the terms of this Seventh Supplemental Indenture. The Guarantees shall be in substantially the form set forth
in Exhibit 3 to the Appendix. 
 (2) The Securities shall be printed, lithographed, typewritten or engraved or produced by any
combination of these methods or may be produced in any other manner permitted by the rules of any automated quotation system or securities exchange (including on steel engraved borders if so required by any automated quotation system or securities
exchange upon which the Securities may be quoted or listed) on which the Securities may be quoted or listed, as the case may be, all as determined by the officers executing such Securities, as evidenced by their execution thereof. 

ARTICLE IV 

Redemption of Securities 
 SECTION 4.1. Optional Redemption. 
 The Company may, at its option, redeem
the Securities, in whole or from time to time in part, prior to the Maturity Date at a Redemption Price equal to the greater of: (i) 100% of the aggregate principal amount of Securities to be redeemed, plus accrued and unpaid interest on the
Securities to the Redemption Date; or (ii) the sum of the present values of the remaining scheduled payments of principal of and interest on the 

 
Securities to be redeemed (exclusive of unpaid interest accrued thereon to the Redemption Date) discounted to the Redemption Date on a semi-annual basis (assuming a 360-day year comprised of
twelve 30-day months) at the Treasury Rate plus 40 basis points, plus unpaid interest on the Securities to be redeemed, accrued to the Redemption Date. 
 SECTION 4.2. Special Mandatory Redemption. 
 If for any reason (i) the
Mergers are not consummated on or prior to the Special Mandatory Redemption Triggering Date or (ii) the Merger Agreement is terminated at any time prior thereto, then the Company shall redeem all the Securities on the Special Mandatory
Redemption Date at a price equal to 101% of the aggregate accreted principal amount of the Securities, plus accrued and unpaid interest from the date of original issuance to, but excluding, the Special Mandatory Redemption Date (the “Special
Mandatory Redemption Price”) (subject to the right of Holders on the relevant Regular Record Date to receive interest due on the relevant Interest Payment Date). 
 SECTION 4.3. Special Mandatory Redemption Procedures. 
 (1) Notice of
redemption pursuant to Section 4.2 (a “Special Mandatory Redemption Notice”) shall be mailed, with a written copy to the Trustee, by first class mail, postage prepaid, within 10 Business Days after the occurrence of the
event triggering redemption to each Holder of Securities at such Holder’s address as shown in the Security Register. Failure to give notice by mailing in the manner herein provided to such Holder, or any defect in the notice to any such Holder,
shall not affect the validity of the proceedings for the redemption of any other Securities. 
 All Special Mandatory Redemption
Notices shall state: 
 (i) the Special Mandatory Redemption Date; 

(ii) the Special Mandatory Redemption Price; 
 (iii) that on the Special Mandatory Redemption Date the Special Mandatory Redemption Price will become due and payable with respect to each Security; 

(iv) the place or places where such Securities are to be surrendered for payment of the Special Mandatory Redemption Price; 

(v) the CUSIP, ISIN or Common Code numbers of such Securities, if any (or any other numbers used by the Depositary to identify such
Securities); and 
 (vi) if funds sufficient to pay the Special Mandatory Redemption Price of all Securities to be redeemed on
the Special Mandatory Redemption Date are deposited with the Paying Agent on or before such Special Mandatory Redemption Date, that such Securities shall cease to bear interest on and after such Special Mandatory Redemption Date. 

 (2) Each Special Mandatory Redemption Notice having been given as aforesaid, the Securities
shall, on the Special Mandatory Redemption Date, become due and payable at the Special Mandatory Redemption Price therein specified. If funds sufficient to pay the Special Mandatory Redemption Price of all Securities to be redeemed on the Special
Mandatory Redemption Date are deposited with the Paying Agent on or before such Special Mandatory Redemption Date, the Securities shall cease to bear interest on and after such Special Mandatory Redemption Date (unless the Company shall default on
the payment of the Special Mandatory Redemption Price). Upon surrender of any such Security for redemption in accordance with said notice, such Security shall be paid by the Company at the Special Mandatory Redemption Price; provided,
however, that installments of interest whose Interest Payment Date is on or prior to the Special Mandatory Redemption Date shall be payable to the Holders of such Securities, or one or more Predecessor Securities, registered as such at the close
of business on the relevant Regular Record Date according to their terms and the provisions of Section 3.7 of the Indenture. 
 (3) If any Security called for redemption shall not be so paid upon surrender thereof for redemption, the principal thereof shall, until paid, bear interest from the Special Mandatory Redemption Date at
the rate borne by the Security. 
 ARTICLE V 
 Remedies 
 SECTION 5.1. Events of Default. 

With respect to the Securities, Section 5.1 of the Base Indenture is hereby amended to add the following as Section 5.1(9):

 (i) the Company fails to timely deliver a Special Mandatory Redemption Notice when required. 

ARTICLE VI 

Reports by Company 
 SECTION 6.1. Reports by Express Scripts or the Company. 
 With respect to
the Securities, Section 7.4 of the Base Indenture is hereby amended to add the following paragraph to the end of such Section: 
 In addition, prior to the consummation of the Mergers, Express Scripts and, following the consummation of the Mergers, the Company, shall furnish, at the Company’s expense, to the Holders and
prospective Holders, upon the requests of such Holders, any information required to be delivered pursuant to Rule 144A(d)(4) (or any successor provision) under the Securities Act so long as any Securities are not freely transferable under the
Securities Act. 

 ARTICLE VII 
 Supplemental Indentures 
 SECTION 7.1. Supplemental Indentures Without
Consent of Holders. 
 Section 9.1 of the Base Indenture shall not be applicable to the Securities. 

Without seeking the consent of any Holders, the Company, together with the Trustee, at any time and from time to time, may modify and
amend the Base Indenture, this Seventh Supplemental Indenture and the terms of the Securities to: 
 (1) allow the
Company’s or any Guarantor’s successor (or successive successors) to assume the Company’s or such Guarantor’s obligations under the Base Indenture, this Seventh Supplemental Indenture and the Securities pursuant to the provisions
under Article VIII or Section 13.15 of the Base Indenture; 
 (2) add to the covenants of the Company for the benefit of
the Holders of the Securities or to surrender any right or power herein conferred upon the Company under this Seventh Supplemental Indenture, the Base Indenture or the Securities; 

(3) add any additional Events of Default; 
 (4) secure the Securities; 
 (5) provide for a successor Trustee with respect to
the Securities and add to or change any of the provisions of the Base Indenture as shall be necessary to provide for or facilitate the administration of the trusts hereunder by more than one Trustee, pursuant to the requirements of Section 6.11
of the Base Indenture; 
 (6) add or release a Guarantor as required or permitted by the Indenture; 

(7) cure any ambiguity, defect or inconsistency; 
 (8) amend the provisions of the Base Indenture or this Seventh Supplemental Indenture relating to the transfer or legending of the Securities; provided that (i) compliance with the Base
Indenture or this Seventh Supplemental Indenture as so amended would not result in Securities being transferred in violation of the Securities Act or any other applicable securities law and (ii) such amendment does not adversely affect the
interests of the Holders of the Securities or owners of beneficial interests in Securities; or 
 (9) make any other amendment
or supplement to the Base Indenture, this Seventh Supplemental Indenture or the Securities, as long as that amendment or supplement does not adversely affect the interests of the Holders of any Securities in any material respect (to be evidenced by
an Opinion of Counsel). 

 No amendment to cure any ambiguity, defect or inconsistency in the Base Indenture, this
Seventh Supplemental Indenture or the Securities made solely to conform to the provisions of the Base Indenture, this Seventh Supplemental Indenture or the Securities to any description of the Securities in the offering circular therefor, to the
extent that such provision in the offering circular was intended to be a verbatim recitation of a provision of the Base Indenture, this Seventh Supplemental Indenture or the Securities, shall be deemed to adversely affect the interests of the
Holders of any Securities. 
 SECTION 7.2. Supplemental Indentures With Consent of Holders. 

Section 9.2 of the Base Indenture shall not be applicable to the Securities. 

The Company, together with the Trustee, may modify and amend this Seventh Supplemental Indenture, the Base Indenture and the terms of the
Securities with the written consent of the Holders of at least a majority in aggregate principal amount of the Outstanding Securities; provided that no modification or amendment may, without the consent of each affected Holder of each
Security: 
 (1) change the Stated Maturity of the principal of, or any installment of or interest on, the Securities;

 (2) reduce the principal amount of, or any premium, if any, or rate of interest on, the Securities; 

(3) reduce any amount payable upon the redemption of the Securities or, except as expressly provided elsewhere herein, change the time at
which the Securities may be redeemed pursuant to Section 4.1 hereof; 
 (4) change any Place of Payment where, or the
currency in which, any principal of, or premium, if any, or interest on, the Securities are payable; 
 (5) impair the right of
any Holder of a Security to receive payment of principal of and interest on such Holder’s Security on or after the Stated Maturity or Redemption Date or to institute suit for the enforcement of any payment on, or with respect to, any Security
on or after the Stated Maturity or Redemption Date; 
 (6) reduce the percentage in principal amount of the Outstanding
Securities, the consent of whose Holders is required for modification or amendment of the Base Indenture or this Seventh Supplemental Indenture, for waiver of compliance with certain provisions of the Base Indenture or this Seventh Supplemental
Indenture or waiver of certain Defaults; 
 (7) release any Guarantor from any of its obligations under its Guarantee or the
Base Indenture or this Seventh Supplemental Indenture other than in accordance with the terms thereof or hereof; or 
 (8)
modify any of the above provisions. 

 Any modification or amendment to, or waiver of, the provisions of this Seventh Supplemental
Indenture and the terms of the Securities that relate to the Special Mandatory Redemption set forth in Sections 4.2 or 4.3 shall require the written consent of the Holders of at least 66 2/3% in aggregate principal amount of the Outstanding
Securities. In addition, any modification or amendment to, or waiver of, the provisions in the Indenture and the terms of the Securities that relate to the items set forth in Section 10.10 of the Base Indenture shall require the written consent
of at least a majority in principal amount of the Outstanding Securities. 
 In addition, the Holders of at least a majority in
aggregate principal amount of the Outstanding Securities may, on behalf of the Holders of all the Securities, waive any past default under the Base Indenture or this Seventh Supplemental Indenture and its consequences, except a default in the
payment of the principal of, or premium, if any, or interest on, any Securities or in respect of a covenant or provision that under the Base Indenture or this Seventh Supplemental Indenture cannot be modified or amended without the consent of each
Holder. In addition, the Holders of at least a majority in aggregate principal amount of the Outstanding Securities may, on behalf of the Holders of all Securities, waive compliance with the Company’s covenants described under Sections 10.8 and
10.9 of the Indenture. 
 ARTICLE VIII 
 Miscellaneous. 
 SECTION 8.1. Governing Law; Waiver of Jury Trial

 THIS SEVENTH SUPPLEMENTAL INDENTURE, THE GUARANTEES AND THE SECURITIES SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE
WITH THE LAWS OF THE STATE OF NEW YORK. EACH OF THE COMPANY AND THE TRUSTEE HEREBY IRREVOCABLY WAIVES, TO THE FULLEST EXTENT PERMITTED BY APPLICABLE LAW, ANY AND ALL RIGHT TO TRIAL BY JURY IN ANY LEGAL PROCEEDING ARISING OUT OF OR RELATING TO THIS
SEVENTH SUPPLEMENTAL INDENTURE, THE GUARANTEES, THE SECURITIES OR THE TRANSACTION CONTEMPLATED HEREBY. 
 SECTION 8.2.
Supplemental Indenture May be Executed in Counterparts. 
 This Seventh Supplemental Indenture may be executed in any
number of counterparts, each of which so executed shall be deemed to be an original, but all such counterparts shall together constitute but one and the same instrument. The exchange of copies of this Seventh Supplemental Indenture and of signature
pages by facsimile or PDF transmission shall constitute effective execution and delivery of this Seventh Supplemental Indenture as to the parties hereto and may be used in lieu of the original Seventh Supplemental Indenture for all purposes.
Signatures of the parties hereto transmitted by facsimile or PDF shall be deemed to be their original signatures for all purposes. 

 SECTION 8.3. Separability Clause. 

In case any provision in this Indenture or in the Securities shall be invalid, illegal or unenforceable, the validity, legality and
enforceability of the remaining provisions shall not in any way be affected or impaired thereby. 

 IN WITNESS WHEREOF, the parties hereto have caused this Seventh Supplemental Indenture to be
duly executed all as of the day and year first above written. 
 [Signature Pages To Follow] 

  

					
	ARISTOTLE HOLDING, INC.
		
	By:	 	 /s/ George Paz

		 	Name:	 	George Paz
		 	Title:	 	Chairman, Chief Executive Officer and President
	
	EXPRESS SCRIPTS, INC.
		
	By:	 	 /s/ George Paz

		 	Name:	 	George Paz
		 	Title:	 	Chairman, Chief Executive Officer and President
	
	 AIRPORT HOLDINGS, LLC
 ESI REALTY, LLC

	By: Express Scripts, Inc., as sole Member
		
	By:	 	 /s/ George Paz

		 	Name:	 	George Paz
		 	Title:	 	Chairman, Chief Executive Officer and President

  
 [Seventh
Supplemental Indenture] 

  

					
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	 SPECIALTY INFUSION PHARMACY, INC.

	 SPECTRACARE, INC.

	 SPECTRACARE HEALTH CARE VENTURES, INC.

	 SPECTRACARE INFUSION PHARMACY, INC.

	 VALUE HEALTH, INC.

	 YOURPHARMACY.COM, INC.

		
	By:	 	 /s/ Keith J. Ebling

		 	Name:	 	Keith J. Ebling
		 	Title:	 	Vice President

  
 [Seventh
Supplemental Indenture] 

  

					
	 CURASCRIPT, INC.

	 ESI MAIL PHARMACY SERVICE, INC.

	 EXPRESS SCRIPTS SPECIALTY DISTRIBUTION SERVICES, INC.

	 EXPRESS SCRIPTS UTILIZATION MANAGEMENT CO.

	 MOORESVILLE ON-SITE PHARMACY, LLC

		
	By:	 	 /s/ Patrick McNamee

		 	Name:	 	Patrick McNamee
		 	Title:	 	President

  
 [Seventh
Supplemental Indenture] 

  

					
	ESI-GP HOLDINGS, INC.
	ESI RESOURCES, INC.
		
	By:	 	 /s/ Tom Rocheford

		 	Name:	 	Tom Rocheford
		 	Title:	 	President
	
	ESI PARTNERSHIP
		
	By:	 	Express Scripts, Inc., as Partner
		
	By:	 	 /s/ Martin P. Akins

		 	Name:	 	Martin P. Akins
		 	Title:	 	Vice President and Deputy General Counsel
		
	By:	 	ESI-GP Holdings, Inc., as Partner
		
	By:	 	 /s/ Tom Rocheford

		 	Name:	 	Tom Rocheford
		 	Title:	 	President

  
 [Seventh
Supplemental Indenture] 

  

					
	SPECTRACARE OF INDIANA
		
	By:	 	Spectracare, Inc., as Partner
		
	By:	 	 /s/ Keith J. Ebling

		 	Name:	 	Keith J. Ebling
		 	Title:	 	Vice President
		
	By:	 	Care Continuum, Inc., as Partner
		
	By:	 	 /s/ Keith J. Ebling

		 	Name:	 	Keith J. Ebling
		 	Title:	 	Vice President
	
	EXPRESS SCRIPTS MSA, LLC
	EXPRESS SCRIPTS WC, INC.
		
	By:	 	 /s/ Edward Ignaczak

		 	Name:	 	Edward Ignaczak
		 	Title:	 	President
	
	 EXPRESS SCRIPTS SENIOR CARE, INC.

	 EXPRESS SCRIPTS SENIOR CARE HOLDINGS, INC.

		
	By:	 	 /s/ George Paz

		 	Name:	 	George Paz
		 	Title:	 	President
	
	 EXPRESS SCRIPTS CANADA HOLDING, LLC

		
	By:	 	 /s/ Keith J. Ebling

		 	Name:	 	Keith J. Ebling
		 	Title:	 	Vice President

  
 [Seventh
Supplemental Indenture] 

  

					
	 Wells Fargo Bank, National Association,
 As Trustee

		
	By:	 	 /s/ Richard Prokosch

		 	Name:	 	Richard Prokosch
		 	Title:	 	Vice President

  
 [Seventh
Supplemental Indenture] 

 RULE 144A/REGULATION S APPENDIX 

PROVISIONS RELATING TO INITIAL SECURITIES, 
 PRIVATE EXCHANGE SECURITIES 
 AND EXCHANGE SECURITIES 

1. Definitions 

1.1 Definitions 
 For the purposes of this Appendix the following terms shall have the meanings indicated below: 
 “Applicable Procedures” means, with respect to any transfer or transaction prior to the expiration of the Restricted Period and involving a Regulation S Global Security or beneficial
interest therein, the rules and procedures of the Depository for such a transfer or transaction, to the extent applicable and as in effect from time to time. 
 “Definitive Security” means a certificated Initial Security or Exchange Security or Private Exchange Security bearing, if required, the appropriate restricted securities legend set forth
in Section 2.3(e). 
 “Depository” means The Depository Trust Company, its nominees and their respective
successors. 
 “Exchange Securities” means any securities issued pursuant to the Indenture in connection with a
Registered Exchange Offer pursuant to a Registration Rights Agreement. 
 “Initial Purchaser” means with
respect to each issuance of Initial Securities, the Persons purchasing such Initial Securities under the related Purchase Agreement. 
 “Initial Securities” means any securities other than Exchange Securities and Private Exchange Securities issued pursuant to the Indenture. 

“Issue Date” means the date on which Initial Securities are issued pursuant to a supplemental indenture to the Base
Indenture or an Officers’ Certificate pursuant to Section 3.1 of the Base Indenture. 
 “Private
Exchange” means the offer by the Company, pursuant to a Registration Rights Agreement, to the Initial Purchaser to issue and deliver to the Initial Purchaser, in exchange for the Initial Securities held by the Initial Purchaser as part of
its initial distribution, a like aggregate principal amount of Private Exchange Securities. 
 “Private Exchange
Securities” means any securities issued in connection with a Private Exchange. 

 “Purchase Agreement” means with respect to each issuance of Initial
Securities, the purchase agreement or underwriting agreement among the Company, the Guarantors and the Persons purchasing such Securities. 
 “QIB” means a “qualified institutional buyer” as defined in Rule 144A. 
 “Registered Exchange Offer” means an offer by the Company, pursuant to a Registration Rights Agreement, to certain Holders of Initial Securities, to issue and deliver to such Holders, in
exchange for the Initial Securities, a like aggregate principal amount of Exchange Securities registered under the Securities Act. 
 “Registration Rights Agreement” means, with respect to each issuance of Securities issued in a transaction exempt from the registration requirements of the Securities Act, the
registration rights agreement, if any, among the Company, the Guarantors and the Persons purchasing such Securities under the related Purchase Agreement. 
 “Restricted Period” means, with respect to any Securities, the period of 40 consecutive days beginning on and including the later of (i) the day on which such Securities are first
offered to Persons other than distributors (as defined in Regulation S under the Securities Act) in reliance on Regulation S and (ii) the issue date with respect to such Securities. 

“Rule 144A Securities” means all Securities offered and sold to QIBs in reliance on Rule 144A. 

“Securities Act” means the Securities Act of 1933, as amended. 

“Securities Custodian” means the custodian with respect to a Global Security (as appointed by the Depository), or any
successor Person thereto and shall initially be the Trustee. 
 “Shelf Registration Statement” means the shelf
registration statement filed by the Company in connection with the offer and sale of Initial Securities or Private Exchange Securities pursuant to a Registration Rights Agreement. 

“Transfer Restricted Securities” means Securities that bear or are required to bear the legend relating to restrictions
on transfer relating to the Securities Act set forth in Section 2.3(e) hereto. 

  
 2 

 1.2 Other Definitions 

 

					
	 Term
	  	Defined in Section:	 
		
	 “Agent Members”
	  	 	2.1	(b) 
		
	 “Clearstream, Luxembourg”
	  	 	2.1	(a) 
		
	 “Euroclear”
	  	 	2.1	(a) 
		
	 “Global Securities”
	  	 	2.1	(a) 
		
	 “Regulation S”
	  	 	2.1	(a) 
		
	 “Regulation S Global Security”
	  	 	2.1	(a) 
		
	 “Regulation S Permanent Global Security”
	  	 	2.1	(a) 
		
	 “Regulation S Temporary Global Security”
	  	 	2.1	(a) 
		
	 “Restricted Securities Legend”
	  	 	2.3	(e) 
		
	 “Rule 144A”
	  	 	2.1	(a) 
		
	 “Rule 144A Global Security”
	  	 	2.1	(a) 

 2. The Securities. 
 2.1(a) Form and Dating. The Initial Securities were offered and sold by the Company pursuant to a Purchase Agreement. The Initial Securities will be resold initially only to (i) QIBs in
reliance on Rule 144A under the Securities Act (“Rule 144A”) and (ii) in offshore transactions to Persons other than U.S. Persons (as defined in Regulation S) in reliance on Regulation S under the Securities Act
(“Regulation S”). Initial Securities may thereafter be transferred to, among others, QIBs and purchasers in reliance on Regulation S, subject to the restrictions on transfer set forth herein. Initial Securities initially resold
pursuant to Rule 144A shall be issued initially in the form of one or more securities in registered, global form (collectively, the “Rule 144A Global Security”); and Initial Securities initially resold pursuant to Regulation S shall
be issued initially in the form of one or more temporary securities in registered, global form (collectively, the “Regulation S Temporary Global Security”), in each case without interest coupons and with the global securities legend
and the applicable restricted securities legend set forth Section 2.3(e) hereto, which shall be deposited on behalf of the purchasers of the Initial Securities represented thereby with the Securities Custodian and registered in the name of the
Depository or a nominee of the Depository, duly executed by the Company and authenticated by the Trustee as provided in the Base Indenture. Until the expiration of the Restricted Period, beneficial ownership interests in the Regulation S Temporary
Global Securities may be held only through Euroclear Bank S.A./N.V., as operator of the Euroclear System (“Euroclear”), and Clearstream Banking, société anonyme (“Clearstream, 

  
 3 

 
Luxembourg”), as indirect participants in DTC, unless transferred to a Person that takes delivery through a Rule 144A Global Security in accordance with the certification requirements
described in the second succeeding paragraph below. Except as set forth in this Section 2.1(a), beneficial ownership interests in a Regulation S Temporary Global Security will not be exchangeable for interests in the Rule 144A Global
Security or any other Security prior to the expiration of the Restricted Period and then, after the expiration of the Restricted Period, may be exchanged for one or more permanent securities in registered, global form without interest coupons
(collectively, the “Regulation S Permanent Global Security” and, together with the Regulation S Temporary Global Security, the “Regulation S Global Security”) or a Definitive Security upon (1) delivery to DTC
of certification of compliance with the transfer restrictions applicable to the Securities and pursuant to Regulation S as provided in the Indenture, (2) a certification in form satisfactory to the Trustee that beneficial ownership interests in
such Regulation S Temporary Global Security are owned either by non-U.S. persons or U.S. persons who purchased such interests in a transaction that did not require registration under the Securities Act and (3) in the case of an exchange for
Definitive Securities, in compliance with the requirements described in Section 2.4(a) of this Appendix. 
 Definitive
Securities may not be exchanged for beneficial interests in any Global Security unless the transferor first delivers to the Trustee a written certificate (in the form provided in the Indenture) to the effect that such transfer will comply with the
appropriate transfer restrictions applicable to such Securities. 
 Prior to the expiration of the Restricted Period, beneficial
interests in Regulation S Global Securities may be exchanged for interests in Rule 144A Global Securities only if (1) such exchange occurs in connection with a transfer of Securities pursuant to Rule 144A and (2) the transferor of the
beneficial interest in the Regulation S Global Security first delivers to the Trustee a written certificate (in the form provided in the Indenture) to the effect that the beneficial interest in the Regulation S Global Security is being transferred
to a Person (a) whom the transferor reasonably believes to be a QIB, (b) is purchasing for its own account or the account of a QIB in a transaction meeting the requirements of Rule 144A, and (c) in accordance with all applicable
securities laws of the states of the United States and other jurisdictions. 
 Beneficial interests in a Rule 144A Global
Security may be transferred to a Person who takes delivery in the form of an interest in a Regulation S Global Security, whether before or after the expiration of the Restricted Period, only if the transferor first delivers to the Trustee a
written certificate (in the form provided in the Indenture) to the effect that such transfer is being made in accordance with Rule 903 or 904 of Regulation S or Rule 144 (if available) under the Securities Act. 

The Rule 144A Global Security, the Regulation S Global Security and any Global Securities in fully registered form without the Restricted
Securities Legend are collectively referred to herein as “Global Securities.” The aggregate principal amount of the Global Securities may from time to time be increased or decreased by adjustments made on the records of the Trustee
and the Depository or its nominee as hereinafter provided. 
 (b) Book-Entry Provisions. This Section 2.1(b) shall
apply only to a Global Security deposited with or on behalf of the Depository. 

  
 4 

 The Company shall execute and the Trustee shall, in accordance with this
Section 2.1(b), authenticate and deliver initially one or more Global Securities that (a) shall be registered in the name of the Depository for such Global Security or Global Securities or the nominee of such Depository and (b) shall
be delivered by the Trustee to such Depository or pursuant to such Depository’s instructions or held by the Trustee as custodian for the Depository. 
 Members of, or participants in, the Depository (“Agent Members”) shall have no rights under the Indenture with respect to any Global Security held on their behalf by the Depository or by
the Trustee as the custodian of the Depository or under such Global Security, and the Company, the Trustee and any agent of the Company or the Trustee shall be entitled to treat the Depository as the absolute owner of such Global Security for all
purposes whatsoever. Notwithstanding the foregoing, nothing herein shall prevent the Company, the Trustee or any agent of the Company or the Trustee from giving effect to any written certification, proxy or other authorization furnished by the
Depository or impair, as between the Depository and its Agent Members, the operation of customary practices of such Depository governing the exercise of the rights of a holder of a beneficial interest in any Global Security. 

(c) Definitive Securities. Except as provided in this Section 2.1 or Section 2.3 or 2.4, owners of beneficial interests
in Global Securities shall not be entitled to receive physical delivery of Definitive Securities. 
 2.2
Authentication. The Trustee shall authenticate and deliver: (1) on the Issue Date, Initial Securities in an aggregate principal amount specified in the written order of the Company pursuant to Section 3.3 of the Indenture,
(2) Exchange Securities or Private Exchange Securities for issue only in a Registered Exchange Offer or a Private Exchange, respectively, pursuant to a Registration Rights Agreement, for a like principal amount of Initial Securities, and
(3) a Global Security without the Restricted Securities Legend pursuant to Section 2.3(e) of this Appendix, in each case upon a Company Order. Such Company Order shall specify the amount of the Securities to be authenticated and the date
on which the original issue of Securities is to be authenticated. 
 2.3 Transfer and Exchange. 

(a) Transfer and Exchange of Definitive Securities. When Definitive Securities are presented to the Security Registrar with a
request: 
  

	 	(x)	to register the transfer of such Definitive Securities; or 

  

	 	(y)	to exchange such Definitive Securities for an equal principal amount of Definitive Securities of other authorized denominations, 

the Security Registrar shall register the transfer or make the exchange as requested pursuant to the terms of the Indenture and if its reasonable
requirements for such transaction are met; provided, however, that the Definitive Securities surrendered for transfer or exchange: 
 (i) shall be duly endorsed or accompanied by a written instrument of transfer in form reasonably satisfactory to the Company and the Security Registrar, duly executed by the Holder thereof or its attorney
duly authorized in writing; and 

  
 5 

 (ii) if such Definitive Securities are required to bear a restricted
securities legend, they are being transferred or exchanged pursuant to an effective registration statement under the Securities Act, pursuant to Section 2.3(b) or pursuant to clause (A), (B) or (C) below, and are accompanied by the
following additional information and documents, as applicable: 
 (A) if such Definitive Securities are being
delivered to the Security Registrar by a Holder for registration in the name of such Holder, without transfer, a certification from such Holder to that effect; or 

(B) if such Definitive Securities are being transferred to the Company, a certification to that effect; or 

(C) if such Definitive Securities are being transferred (x) pursuant to an exemption from registration in accordance
with Rule 144A, Regulation S or Rule 144 under the Securities Act; or (y) in reliance upon another exemption from the requirements of the Securities Act: (i) a certification to that effect (in the form set forth on the reverse of the
Security) and (ii) if the Company so requests, an opinion of counsel or other evidence reasonably satisfactory to it as to the compliance with the restrictions set forth in the legend set forth in Section 2.3(e)(i). 

(b) Restrictions on Transfer of a Definitive Security for a Beneficial Interest in a Global Security. A Definitive Security
may not be exchanged for a beneficial interest in a Rule 144A Global Security or a Regulation S Global Security except upon satisfaction of the requirements set forth below. Upon receipt by the Trustee of a Definitive Security, duly endorsed or
accompanied by appropriate instruments of transfer, in form satisfactory to the Trustee, together with: 
 (i)
certification, in the form set forth on the reverse of the Security, that such Definitive Security is either (A) being transferred to a QIB in accordance with Rule 144A or (B) being transferred after expiration of the Restricted Period by
a Person who initially purchased such Security in reliance on Regulation S to a buyer who elects to hold its interest in such Security in the form of a beneficial interest in the Regulation S Global Security; and 

(ii) written instructions directing the Trustee to make, or to direct the Securities Custodian to make, an adjustment on
its books and records with respect to such Rule 144A Global Security (in the case of a transfer pursuant to clause (b)(i)(A)) or Regulation S Global Security (in the case of a transfer pursuant to clause (b)(i)(B)) to reflect an increase in the
aggregate principal amount of the Securities represented by the Rule 144A Global Security or Regulation S Global Security, as applicable, such instructions to contain information regarding the Depository account to be credited with such increase,

 then the Trustee shall cancel such Definitive Security and cause, or direct the Securities Custodian to cause, in accordance with the
standing instructions and procedures existing between the Depository and the Securities Custodian, the aggregate principal amount of Securities 

  
 6 

 
represented by the Rule 144A Global Security or Regulation S Global Security, as applicable, to be increased by the aggregate principal amount of the Definitive Security to be exchanged and shall
credit or cause to be credited to the account of the Person specified in such instructions a beneficial interest in the Rule 144A Global Security or Regulation S Global Security, as applicable, equal to the principal amount of the Definitive
Security so canceled. If no Rule 144A Global Securities or Regulation S Global Securities, as applicable, are then outstanding, the Company shall issue and the Trustee shall authenticate, upon written order of the Company in the form of an
Officers’ Certificate of the Company, a new Rule 144A Global Security or Regulation S Global Security, as applicable, in the appropriate principal amount. 
 (c) Transfer and Exchange of Global Securities. 
 (i) The
transfer and exchange of Global Securities or beneficial interests therein shall be effected through the Depository, in accordance with the Indenture (including applicable restrictions on transfer set forth herein, if any) and the procedures of the
Depository therefor. A transferor of a beneficial interest in a Global Security shall deliver to the Security Registrar a written order given in accordance with the Depository’s procedures containing information regarding the participant
account of the Depository to be credited with a beneficial interest in the Global Security. The Security Registrar shall, in accordance with such instructions instruct the Depository to credit to the account of the Person specified in such
instructions a beneficial interest in the Global Security and to debit the account of the Person making the transfer in an amount equal to the beneficial interest in the Global Security being transferred. 

(ii) If the proposed transfer is a transfer of a beneficial interest in one Global Security to a beneficial interest in
another Global Security, the Security Registrar shall reflect on its books and records the date and an increase in the principal amount of the Global Security to which such interest is being transferred in an amount equal to the principal amount of
the interest to be so transferred, and the Security Registrar shall reflect on its books and records the date and a corresponding decrease in the principal amount of the Global Security from which such interest is being transferred. 

(iii) Notwithstanding any other provisions of this Appendix (other than the provisions set forth in Section 2.4), a
Global Security may not be transferred as a whole except by the Depository to a nominee of the Depository or by a nominee of the Depository to the Depository or another nominee of the Depository or by the Depository or any such nominee to a
successor Depository or a nominee of such successor Depository. 
 (iv) In the event that a Global Security is
exchanged for Definitive Securities pursuant to Section 2.4 of this Appendix, prior to the consummation of a Registered Exchange Offer or the effectiveness of a Shelf Registration Statement with respect to such Securities, such Securities may
be exchanged only in accordance with such procedures as are substantially consistent with the provisions of this Section 2.3 (including the certification requirements set forth on the reverse of the Initial Securities intended to ensure that
such transfers comply with Rule 144A, Regulation S or another applicable exemption under the Securities Act, as the case may be) and such other procedures as may from time to time be adopted by the Company. 

  
 7 

 (d) Restrictions on Transfer of Regulation S Global Securities. During the Restricted
Period, beneficial ownership interests in Regulation S Global Securities may only be sold, pledged or transferred in accordance with the Applicable Procedures and only (i) to the Company, (ii) in an offshore transaction in accordance with
Regulation S or (iii) pursuant to an effective registration statement under the Securities Act, in each case in accordance with any applicable securities laws of any State of the United States. 

(e) Legend. 
 (i) Except as permitted by the following paragraphs (ii), (iii) and (iv), each Security certificate evidencing the Global Securities (and all Securities issued in exchange therefor or in
substitution thereof), in the case of Securities offered other than in reliance on Regulation S, shall bear a legend in substantially the following form (together with the legend in the second paragraph of this Section 2.3(e)(i), the
“Restricted Securities Legend”): 
 THIS SECURITY (OR ITS PREDECESSOR) WAS ORIGINALLY ISSUED IN A TRANSACTION
EXEMPT FROM REGISTRATION UNDER THE UNITED STATES SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), AND THIS SECURITY MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED IN THE ABSENCE OF SUCH REGISTRATION OR AN APPLICABLE
EXEMPTION THEREFROM. EACH PURCHASER OF THIS SECURITY IS HEREBY NOTIFIED THAT THE SELLER OF THIS SECURITY MAY BE RELYING ON THE EXEMPTION FROM THE PROVISIONS OF SECTION 5 OF THE SECURITIES ACT PROVIDED BY RULE 144A THEREUNDER. 

THE HOLDER OF THIS SECURITY AGREES FOR THE BENEFIT OF THE COMPANY THAT (A) THIS SECURITY MAY BE OFFERED, RESOLD, PLEDGED OR
OTHERWISE TRANSFERRED, ONLY (I) IN THE UNITED STATES TO A PERSON WHOM THE SELLER REASONABLY BELIEVES IS A QUALIFIED INSTITUTIONAL BUYER (AS DEFINED IN RULE 144A UNDER THE SECURITIES ACT) IN A TRANSACTION MEETING THE REQUIREMENTS OF
RULE 144A, (II) OUTSIDE THE UNITED STATES IN AN OFFSHORE TRANSACTION IN ACCORDANCE WITH RULE 904 UNDER THE SECURITIES ACT, (III) PURSUANT TO THE EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT PROVIDED BY RULE 144
THEREUNDER (IF AVAILABLE), OR (IV) PURSUANT TO AN EFFECTIVE REGISTRATION STATEMENT UNDER THE SECURITIES ACT, IN EACH OF CASES (I) THROUGH (IV) IN ACCORDANCE WITH ANY APPLICABLE SECURITIES LAWS OF ANY STATE OF THE UNITED STATES, AND (B) THE
HOLDER 

  
 8 

 
WILL, AND EACH SUBSEQUENT HOLDER IS REQUIRED TO, NOTIFY ANY PURCHASER OF THIS SECURITY FROM IT OF THE RESALE RESTRICTIONS REFERRED TO IN (A) ABOVE. 

Each certificate evidencing a Security offered in reliance on Regulation S shall bear a legend in substantially the
following form: 
 THIS SECURITY (OR ITS PREDECESSOR) WAS ORIGINALLY ISSUED IN A TRANSACTION ORIGINALLY EXEMPT FROM REGISTRATION
UNDER THE U.S. SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), AND MAY NOT BE TRANSFERRED IN THE UNITED STATES OR TO, OR FOR THE ACCOUNT OR BENEFIT OF, ANY U.S. PERSON EXCEPT PURSUANT TO AN AVAILABLE EXEMPTION FROM THE
REGISTRATION REQUIREMENTS OF THE SECURITIES ACT AND ALL APPLICABLE STATE SECURITIES LAWS. TERMS USED ABOVE HAVE THE MEANINGS GIVEN TO THEM IN REGULATION S UNDER THE SECURITIES ACT. 

Each Definitive Security shall also bear the following additional legend: 

IN CONNECTION WITH ANY TRANSFER, THE HOLDER WILL DELIVER TO THE SECURITY REGISTRAR AND TRANSFER AGENT SUCH CERTIFICATES AND OTHER
INFORMATION AS SUCH TRANSFER AGENT MAY REASONABLY REQUIRE TO CONFIRM THAT THE TRANSFER COMPLIES WITH THE FOREGOING RESTRICTIONS. 
 (ii) Upon any sale or transfer of a Transfer Restricted Security (including any Transfer Restricted Security represented by a Global Security) pursuant to Rule 144 under the Securities Act, the Security
Registrar shall permit the transferee thereof to exchange such Transfer Restricted Security for a Definitive Security that does not bear the legend set forth above and rescind any restriction on the transfer of such Transfer Restricted Security, if
the transferor thereof certifies in writing to the Security Registrar that such sale or transfer was made in reliance on Rule 144 (such certification to be in the form set forth on the reverse of the Security); and to the extent permitted by
law at any time after one year has elapsed following the Issue Date, if the Securities are freely tradeable without restriction pursuant to Rule 144 under the Securities Act (or successor rule), the Security Registrar shall permit the removal
of the Restricted Securities Legend and rescind any restriction on the transfer of such Transfer Restricted Security if the Company delivers to the Trustee an opinion reasonably satisfactory to the Trustee that the removal of the Restricted
Securities Legend is in compliance with the Securities Act. 
 (iii) After a transfer of any Initial Securities
or Private Exchange Securities pursuant to and during the period of the effectiveness of a Shelf Registration Statement with respect to such Initial Securities or Private Exchange Securities, as the case may be, all requirements pertaining to
legends on such Initial Security or such Private Exchange 

  
 9 

 
Security will cease to apply and a certificated Initial Security or Private Exchange Security or an Initial Security or Private Exchange Security in global form, in each case without restrictive
transfer legends, will be available to the transferee of the Holder of such Initial Securities or Private Exchange Securities upon exchange of such transferring Holder’s certificated Initial Security or Private Exchange Security or directions
to transfer such Holder’s interest in the Global Security, as applicable. 
 (iv) Upon the consummation of a
Registered Exchange Offer with respect to the Initial Securities, all requirements pertaining to such Initial Securities that Initial Securities issued to certain Holders be issued in global form will still apply with respect to Holders of such
Initial Securities that do not exchange their Initial Securities, and Exchange Securities in certificated or global form, in each case without the restricted securities legend set forth in Exhibit 1 hereto will be available to Holders that
exchange such Initial Securities in such Registered Exchange Offer. 
 (v) Upon the consummation of a Private
Exchange with respect to the Initial Securities, all requirements pertaining to such Initial Securities that Initial Securities issued to certain Holders be issued in global form will still apply with respect to Holders of such Initial Securities
that do not exchange their Initial Securities, and Private Exchange Securities in global form with the global securities legend and the applicable restricted securities legend set forth in Exhibit 1 hereto will be available to Holders that
exchange such Initial Securities in such Private Exchange. 
 (f) Cancellation or Adjustment of Global Security. At such
time as all beneficial interests in a Global Security have either been exchanged for Definitive Securities, redeemed, purchased or canceled, such Global Security shall be returned to the Depository for cancellation or retained and canceled by the
Trustee. At any time prior to such cancellation, if any beneficial interest in a Global Security is exchanged for Definitive Securities, redeemed, purchased or canceled, the principal amount of Securities represented by such Global Security shall be
reduced and an adjustment shall be made on the books and records of the Trustee (if it is then the Securities Custodian for such Global Security) with respect to such Global Security, by the Trustee or the Securities Custodian, to reflect such
reduction. 
 (g) No Obligation of the Trustee. 

(i) The Trustee shall have no responsibility or obligation to any beneficial owner of a Global Security, a member of, or a
participant in the Depository or other Person with respect to the accuracy of the records of the Depository or its nominee or of any participant or member thereof, with respect to any ownership interest in the Securities or with respect to the
delivery to any participant, member, beneficial owner or other Person (other than the Depository) of any notice (including any notice of redemption) or the payment of any amount, under or with respect to such Securities. All notices and
communications to be given to the Holders and all payments to be made to Holders under the Securities shall be given or made only to or upon the order of the registered Holders (which shall be the Depository or its nominee in the case of a Global
Security). The rights of beneficial owners in any Global Security shall be exercised only through the Depository subject to the applicable rules and procedures of the Depository. The Trustee may rely and shall be fully protected in relying upon
information furnished by the Depository with respect to its members, participants and any beneficial owners. 

  
 10 

 (ii) The Trustee shall have no obligation or duty to monitor, determine or
inquire as to compliance with any restrictions on transfer imposed under the Indenture or under applicable law with respect to any transfer of any interest in any Security (including any transfers between or among Depository participants, members or
beneficial owners in any Global Security) other than to require delivery of such certificates and other documentation or evidence as are expressly required by, and to do so if and when expressly required by, the terms of the Indenture, and to
examine the same to determine substantial compliance as to form with the express requirements hereof. 
 2.4 Definitive
Securities. 
 (a) A Global Security deposited with the Depository or with the Trustee as Securities Custodian for the
Depository pursuant to Section 2.1 shall be transferred to the beneficial owners thereof in the form of Definitive Securities in an aggregate principal amount equal to the principal amount of such Global Security, in exchange for such Global
Security, only if such transfer complies with Section 2.3 hereof and (i) the Depository notifies the Company that it is unwilling or unable to continue as Depository for such Global Security or if at any time such Depository ceases to be a
“clearing agency” registered under the Exchange Act, in either case, and a successor depository is not appointed by the Company within 90 days of such notice, (ii) a Default with respect to the Securities has occurred and is
continuing and DTC or the Company specifically requests such exchange, (iii) the Company, at its option, notifies the Trustee in writing that it elects to cause the issuance of Definitive Securities under the Indenture or (iv) upon prior
written notice given to the Trustee by or on behalf of the Depository in accordance with the Indenture. 
 (b) Any Global
Security that is transferable to the beneficial owners thereof pursuant to this Section 2.4 shall be surrendered by the Depository to the Trustee located at its principal corporate trust office in the Borough of Manhattan, The City of New York,
to be so transferred, in whole or from time to time in part, without charge, and the Trustee shall authenticate and deliver, upon such transfer of each portion of such Global Security, an equal aggregate principal amount of Definitive Securities of
authorized denominations. Any portion of a Global Security transferred pursuant to this Section 2.4 shall be executed, authenticated and delivered only in minimum denominations of $2,000 principal amount and any integral multiple of $1,000 in
excess thereof and registered in such names as the Depository shall direct. Any Definitive Security delivered in exchange for an interest in a Transfer Restricted Security shall, except as otherwise provided by Section 2.3(e) hereof, bear the
applicable restricted securities legend and definitive securities legend set forth in Exhibit 1 hereto unless that legend is not required by applicable law. 
 (c) Subject to the provisions of Section 2.4(b) hereof, the registered Holder of a Global Security shall be entitled to grant proxies and otherwise authorize any Person, including Agent Members and
Persons that may hold interests through Agent Members, to take any action which a Holder is entitled to take under the Indenture or the Securities. 

  
 11 

 (d) In the event of the occurrence of one of the events specified in Section 2.4(a)
hereof, the Company shall promptly make available to the Trustee a reasonable supply of Definitive Securities in definitive, fully registered form without interest coupons. 

  
 12 

 APPENDIX 
 EXHIBIT 1 
 [FORM OF FACE OF INITIAL SECURITY] 

[Global Securities Legend] 
 UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (“DTC”), NEW YORK, NEW YORK, TO THE COMPANY OR ITS AGENT FOR
REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NAME OF CEDE & CO. OR SUCH OTHER NAME AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF DTC (AND ANY PAYMENT IS MADE TO CEDE & CO., OR
TO SUCH OTHER ENTITY AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF DTC) ANY TRANSFER, PLEDGE OR OTHER USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL INASMUCH AS THE REGISTERED OWNER HEREOF, CEDE & CO., HAS AN
INTEREST HEREIN. 
 TRANSFERS OF THIS GLOBAL SECURITY SHALL BE LIMITED TO TRANSFERS IN WHOLE, BUT NOT IN PART, TO NOMINEES OF
DTC OR TO A SUCCESSOR THEREOF OR SUCH SUCCESSOR’S NOMINEE AND TRANSFERS OF PORTIONS OF THIS GLOBAL SECURITY SHALL BE LIMITED TO TRANSFERS MADE IN ACCORDANCE WITH THE RESTRICTIONS SET FORTH IN THE INDENTURE REFERRED TO ON THE REVERSE HEREOF.

 [[FOR REGULATION S GLOBAL SECURITY ONLY] UNTIL 40 DAYS AFTER THE LATER OF COMMENCEMENT OR COMPLETION OF THE OFFERING, AN
OFFER OR SALE OF SECURITIES WITHIN THE UNITED STATES BY A DEALER (AS DEFINED IN THE SECURITIES ACT) MAY VIOLATE THE REGISTRATION REQUIREMENTS OF THE SECURITIES ACT IF SUCH OFFER OR SALE IS MADE OTHERWISE THAN IN ACCORDANCE WITH RULE 144A
THEREUNDER.] 
 [Restricted Securities Legend for Securities offered otherwise than in Reliance on Regulation S] 

THIS SECURITY (OR ITS PREDECESSOR) WAS ORIGINALLY ISSUED IN A TRANSACTION EXEMPT FROM REGISTRATION UNDER THE UNITED STATES SECURITIES ACT
OF 1933, AS AMENDED (THE “SECURITIES ACT”), AND THIS SECURITY MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED IN THE ABSENCE OF SUCH REGISTRATION OR AN APPLICABLE EXEMPTION THEREFROM. EACH PURCHASER OF THIS SECURITY IS HEREBY NOTIFIED
THAT THE SELLER OF THIS SECURITY MAY BE RELYING ON THE EXEMPTION FROM THE PROVISIONS OF SECTION 5 OF THE SECURITIES ACT PROVIDED BY RULE 144A THEREUNDER. 
 THE HOLDER OF THIS SECURITY AGREES FOR THE BENEFIT OF THE COMPANY THAT (A) THIS SECURITY MAY BE OFFERED, RESOLD, PLEDGED OR 

  
 1 

 
OTHERWISE TRANSFERRED, ONLY (I) IN THE UNITED STATES TO A PERSON WHOM THE SELLER REASONABLY BELIEVES IS A QUALIFIED INSTITUTIONAL BUYER (AS DEFINED IN RULE 144A UNDER THE SECURITIES
ACT) IN A TRANSACTION MEETING THE REQUIREMENTS OF RULE 144A, (II) OUTSIDE THE UNITED STATES IN AN OFFSHORE TRANSACTION IN ACCORDANCE WITH RULE 904 UNDER THE SECURITIES ACT, (III) PURSUANT TO THE EXEMPTION FROM REGISTRATION UNDER
THE SECURITIES ACT PROVIDED BY RULE 144 THEREUNDER (IF AVAILABLE), OR (IV) PURSUANT TO AN EFFECTIVE REGISTRATION STATEMENT UNDER THE SECURITIES ACT, IN EACH OF CASES (I) THROUGH (IV) IN ACCORDANCE WITH ANY APPLICABLE SECURITIES LAWS OF ANY
STATE OF THE UNITED STATES, AND (B) THE HOLDER WILL, AND EACH SUBSEQUENT HOLDER IS REQUIRED TO, NOTIFY ANY PURCHASER OF THIS SECURITY FROM IT OF THE RESALE RESTRICTIONS REFERRED TO IN (A) ABOVE. 

[Restricted Securities Legend for Securities Offered in Reliance on Regulation S.] 

THIS SECURITY (OR ITS PREDECESSOR) WAS ORIGINALLY ISSUED IN A TRANSACTION ORIGINALLY EXEMPT FROM REGISTRATION UNDER THE U.S. SECURITIES
ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), AND MAY NOT BE TRANSFERRED IN THE UNITED STATES OR TO, OR FOR THE ACCOUNT OR BENEFIT OF, ANY U.S. PERSON EXCEPT PURSUANT TO AN AVAILABLE EXEMPTION FROM THE REGISTRATION REQUIREMENTS OF THE
SECURITIES ACT AND ALL APPLICABLE STATE SECURITIES LAWS. TERMS USED ABOVE HAVE THE MEANINGS GIVEN TO THEM IN REGULATION S UNDER THE SECURITIES ACT. 
 [Definitive Securities Legend] 
 IN CONNECTION WITH ANY TRANSFER, THE HOLDER WILL
DELIVER TO THE SECURITY REGISTRAR AND TRANSFER AGENT SUCH CERTIFICATES AND OTHER INFORMATION AS SUCH TRANSFER AGENT MAY REASONABLY REQUIRE TO CONFIRM THAT THE TRANSFER COMPLIES WITH THE FOREGOING RESTRICTIONS. 

  
 2 

 ARISTOTLE HOLDING, INC. 

3.900% SENIOR NOTE DUE 2022 
  

			
	No.                     	  	Principal Amount (US)$        

 CUSIP NO.
                     
 ISIN NO.
                     

Aristotle Holding, Inc., a corporation organized and existing under the laws of the State of Delaware (herein called the
“Company”, which term includes any successor Person under the Indenture referred to on the reverse hereof), for value received, hereby promises to pay to Cede & Co., or its registered assigns, the principal sum of
                     United States Dollars (U.S.$        ) on February 15, 2022 and to pay
interest thereon, from February 9, 2012, or from the most recent Interest Payment Date to which interest has been paid or duly provided for to but excluding the next Interest Payment Date, which shall be February 15 and August 15 of
each year, commencing August 15, 2012, at the per annum rate of 3.900%, or as such rate may be adjusted pursuant to the terms hereof (the “Security Interest Rate”), until the principal hereof is paid or made available for
payment. 
 The interest so payable, and punctually paid or duly provided for, on any Interest Payment Date will, as provided in
the Indenture, be paid to the Person in whose name this Security is registered at the close of business on the Regular Record Date for such interest, which shall be the day that is 15 days prior to the relevant Interest Payment Date (whether or not
a Business Day). Except as otherwise provided in the Indenture, any such interest not so punctually paid or duly provided for will forthwith cease to be payable to the Holder on such Regular Record Date and may either be paid to the Person in whose
name this Security is registered at the close of business on a Special Record Date for the payment of such Defaulted Interest to be fixed by the Trustee, notice of which shall be given to Holders of Securities not less than 10 days prior to the
Special Record Date, or be paid at any time in any other lawful manner not inconsistent with the requirements of any automated quotation system or securities exchange on which the Securities may be quoted or listed, and upon such notice as may be
required by such exchange, all as more fully provided in the Indenture. Interest will be computed on the basis of a 360-day year comprised of twelve 30-day months. The Company will pay interest on overdue principal at the rate borne by this
Security, and it will pay interest on overdue installments of interest at the same rate to the extent lawful. 
 Subject to the
provisions of the Registration Rights Agreement, if a Registration Default (as defined in the Registration Rights Agreement) occurs, additional interest will accrue on this Security from and including the date on which such Registration Default
occurs to but excluding the date on which all such Registration Defaults have been cured or the Securities cease to be Transfer Restricted Securities (as defined in the Registration Rights Agreement), whichever is earlier, at a rate of
0.25% per annum for the first 90-day period immediately following the occurrence of a Registration Default, and such rate will increase by 0.25% per annum on the 91st day following the occurrence of such Registration Default (provided that
the maximum additional interest rate during the initial 90-day period shall be 0.25% per annum and the maximum additional interest rate thereafter shall be 0.50% per annum, in each case regardless of the number of Registration Defaults
that have occurred and are continuing). The Company will pay such additional interest on regular Interest Payment Dates. 

  
 3 

 The Place of Payment for this Security will be the corporate trust office of the Trustee at
625 Marquette Avenue, 11th Floor, Minneapolis, Minnesota 55479, or as otherwise provided in the Indenture, in such coin or currency of the United States of America as at the time of payment shall be legal tender for the payment of public and private
debts. Payments in respect of the Securities represented by a Global Security (including principal, premium and interest) will be made by wire transfer of immediately available funds to the accounts specified by the Depository. The Company will make
all payments in respect of a Definitive Security (including principal, premium and interest) by mailing a check to the registered address of each Holder thereof as such address appears on the Security Register; provided, however, that
payments on a Definitive Security will be made by wire transfer to a U.S. dollar account maintained by the payee with a bank in the United States if such Holder elects payment by wire transfer by giving written notice to the Trustee or the Paying
Agent to such effect designating such account no later than 30 days immediately preceding the relevant due date for payment (or such other date as the Trustee may accept in its discretion). 

Reference is hereby made to the further provisions of this Security set forth on the reverse hereof, which further provisions shall for
all purposes have the same effect as if set forth at this place. 
 Unless the certificate of authentication hereon has been
executed by the Trustee referred to on the reverse hereof by manual signature, this Security shall not be entitled to any benefit under the Indenture or be valid or obligatory for any purpose. 

  
 4 

 IN WITNESS WHEREOF, the Company has caused this instrument to be duly executed. 

 

			
	ARISTOTLE HOLDING, INC.
		
	By:	 	  

	Name:	 	
	Title:	 	

  

			
	Attest:
		
	By:	 	  

	Name:	 	
	Title:	 	

  
 5 

 CERTIFICATE OF AUTHENTICATION 
 This is one of the Securities of the series designated referred to in the within-mentioned Indenture. 
 Dated: 
  

			
	WELLS FARGO BANK, NATIONAL ASSOCIATION,
	as Trustee
		
	By:	 	  

		 	Authorized Signatory

  
 6 

 [FORM OF REVERSE OF SECURITY] 

(1) Indenture. This Security is one of a duly authorized issue of securities of the Company designated as its “3.900%
Senior Notes due 2022” (herein called the “Securities”), issued under a Seventh Supplemental Indenture, dated as of February 9, 2012, to an indenture, dated as of November 21, 2011 (as it may be amended or
supplemented from time to time in accordance with the terms thereof and herein with the Seventh Supplemental Indenture, collectively, the “Indenture”), between the Company, the Guarantors and Wells Fargo Bank, National Association,
as Trustee (herein called the “Trustee,” which term includes any successor trustee under the Indenture), to which reference is hereby made for a statement of the respective rights, limitations of rights, duties and immunities
thereunder of the Company, the Guarantors, the Trustee and the Holders of the Securities and of the terms upon which the Securities are, and are to be, authenticated and delivered. The aggregate principal amount of Initial Securities Outstanding at
any time may not exceed $1,000,000,000 in aggregate principal amount, except for Securities issued, authenticated and delivered upon registration or transfer of, or in exchange for, or in lieu of, other Securities pursuant to Sections 3.4, 3.5, 3.6,
9.6 or 11.7 of the Base Indenture and except for any Securities which, pursuant to Section 3.3 of the Base Indenture, are deemed never to have been authenticated and delivered. The Seventh Supplemental Indenture pursuant to which this Security
is issued provides that Additional Securities may be issued thereunder, if certain conditions are met. The Initial Securities issued pursuant to the Seventh Supplemental Indenture and all Exchange Securities or Private Exchange Securities issued in
exchange therefor will be treated as a single class for all purposes under the Indenture. 
 The Indenture contains covenants
that limit the ability of the Company and any Restricted Subsidiary to create liens on assets and to engage in sale/leaseback transactions. The Indenture also contains covenants that limit the ability of the Company and, prior to the consummation of
the Mergers, of Express Scripts to consolidate, merge or transfer all or substantially all of their respective assets. These covenants are subject to important exceptions and qualifications. 

All terms used in this Security which are defined in the Indenture (including in the Appendix thereto) shall have the meanings assigned
to them in the Indenture. In the event of a conflict or inconsistency between this Security and the Indenture, the provisions of the Indenture shall govern. 
 (2) Optional Redemption. At any time prior to Maturity, the Company may at its option redeem all or a part of the Securities upon not more than 60 nor less than 30 days prior notice, at a
Redemption Price equal to the greater of: (i) 100% of the aggregate principal amount of any Securities being redeemed, plus accrued and unpaid interest on the Securities to the Redemption Date; or (ii) the sum of the present values of the
remaining scheduled payments of principal of and interest on the Securities to be redeemed (exclusive of unpaid interest accrued thereon to the Redemption Date) discounted to the Redemption Date on a semi-annual basis (assuming a 360-day year
comprised of twelve 30-day months) at the Treasury Rate plus 40 basis points, plus unpaid interest on the Securities to be redeemed, accrued to the Redemption Date. 

  
 7 

 (3) Mandatory Redemption. Except as provided in Sections 4 and 5 below, the Company
is not required to make mandatory redemption or sinking fund payments with respect to the Securities. 
 (4) Special
Mandatory Redemption. If for any reason (i) the Mergers are not consummated on or prior to the Special Mandatory Redemption Triggering Date or (ii) the Merger Agreement is terminated at any time prior thereto, then the Company shall
redeem all the Securities on the Special Mandatory Redemption Date at a price equal to 101% of the aggregate accreted principal amount of such Security, plus accrued and unpaid interest from the date of original issuance to, but excluding, the
Special Mandatory Redemption Date (subject to the right of Holders on the relevant Regular Record Date to receive interest due on the relevant Interest Payment Date). 
 (5) Change of Control Triggering Event. In the event of a Change of Control Triggering Event, the Holders may require the Company to purchase for cash all or a portion of their Securities at a
purchase price equal to 101% of the aggregate principal amount of the Securities repurchased, plus accrued and unpaid interest, if any, pursuant to the provisions of Section 10.10 of the Base Indenture. 

(6) Registration Rights. The Company is party to a Registration Rights Agreement, dated as of February 9, 2012, among the
Company, the Guarantors and the representatives of the Initial Purchasers named therein, pursuant to which it is obligated to pay additional interest on the Securities upon the occurrence of certain events specified in the Registration Rights
Agreement. 
 (7) Global Security. If this Security is a Global Security, then the transfer and exchange of this Security
or beneficial interests herein shall be effected through the Depository in accordance with the Indenture (including applicable restrictions on transfer set forth therein, if any) and the procedures of the Depository therefor. The Security Registrar
shall make an adjustment on its records to reflect such deposit or withdrawal in accordance with the Depository’s Procedures. 
 (8) Defaults and Remedies. If an Event of Default with respect to this Security occurs and is continuing, the principal of and any unpaid premium and interest on (or, if this Security is an
Original Issue Discount Security, such portion of the principal amount of such Securities as may be specified in the terms thereof) all outstanding securities of this series, may be declared due and payable in the manner and with the effect provided
in the Indenture. The Holders of at least a majority in principal amount of the Outstanding Securities may rescind or annul that acceleration if all Events of Default with respect to the Securities other than the non-payment of accelerated principal
have been cured or waived as provided in the Indenture. 
 As provided in and subject to the provisions of the Indenture, the
Holder of this Security shall not have the right to institute any proceeding with respect to the Indenture or for the appointment of a receiver or trustee or for any other remedy thereunder, unless such Holder shall have previously given the Trustee
written notice of a continuing Event of Default, and, among other things, the Holders of not less than 25% in aggregate principal amount of the Outstanding Securities shall have made a written request to the Trustee to pursue a remedy in

  
 8 

 
respect of such Event of Default as Trustee. The foregoing shall not apply to any suit instituted by the Holder of this Security for the enforcement of any amounts due on the Securities on or
after the respective due dates expressed herein. 
 (9) Discharge and Defeasance. Subject to certain conditions, the
Company at any time shall be entitled to terminate some or all of the Company’s and the Guarantors’ obligations under the Securities, the Guarantees and the Indenture if the Company deposits with the Trustee money or U.S. Government
Obligations for the payment of principal and interest on the Securities to redemption or maturity, as the case may be. 
 (10)
Amendment, Supplement and Waiver. The Indenture permits, with certain exceptions as therein provided, the amendment thereof and the modification of the rights and obligations of the Company and the rights of the Holders of the Securities
under the Indenture at any time by the Company and the Trustee with the written consent of the Holders of at least a majority in aggregate principal amount of the Outstanding Securities. The provisions relating to the Special Mandatory Redemption
set forth in Sections 4.2 and 4.3 of the Seventh Supplemental Indenture may not be modified or waived without the written consent of 66 2/3% in aggregate principal amount of the Outstanding Securities. The Indenture also contains provisions
permitting the Holders of specified percentages in principal amount of the Outstanding Securities, on behalf of the Holders of all such Securities, to waive compliance by the Company with certain provisions of the Indenture and certain past defaults
under the Indenture and their consequences. Any such consent or waiver by the Holder of this Security shall be conclusive and binding upon such Holder and upon all future Holders of this Security and of any Security issued upon the registration of
transfer hereof or in exchange herefor or in lieu hereof whether or not notation of such consent or waiver is made upon this Security or such other Security. Certain modifications or amendments to the Indenture require the consent of the Holder of
each Outstanding Security affected. 
 Notwithstanding any other provision of the Indenture or this Security, the Holder of this
Security shall have the right, which is absolute and unconditional, to receive payment of the principal of and any premium and (subject to Section 3.7 of the Base Indenture) interest on any such Security on the Stated Maturity date expressed
herein (or, in the case of redemption, on the Redemption Date) and to institute suit for the enforcement of any such payment, and such rights shall not be impaired without the consent of such Holder. 

(11) Denomination, Registration and Transfer. The Securities are in registered form without coupons in minimum denominations of
$2,000 principal amount and integral multiples of $1,000 in excess thereof. As provided in the Indenture and subject to certain limitations therein set forth, this Security is transferable only upon surrender of this Security for registration of
transfer. Upon surrender for registration of transfer of this Security at the office or agency of the Company in a Place of Payment for this Security, the Company, if the requirements of the Indenture are met, shall execute, and the Trustee shall
authenticate and deliver, in the name of the designated transferee or transferees, one or more new Securities of authorized denominations and of like tenor and aggregate principal amount, and having endorsed thereon a Guarantee executed by the
Guarantors. 

  
 9 

 If the requirements of this Indenture are met, then, at the option of the Holder, Securities
may be exchanged for other Securities, of any authorized denominations and of like tenor and aggregate principal amount, upon surrender of the Securities to be exchanged at such office or agency. Whenever any Securities are so surrendered for
exchange, the Company shall execute, and the Trustee shall authenticate and deliver, the Securities which the Holder making the exchange is entitled to receive, and having endorsed thereon a Guarantee executed by the Guarantor. No service charge
shall be made for any such registration of transfer or exchange, but the Company may require payment of a sum sufficient to cover any tax or other governmental charge that may be imposed in connection therewith. 

Prior to due presentment of this Security for registration of transfer, the Company, the Guarantors, the Trustee and any agent of the
Company, the Guarantors or the Trustee may treat the Person in whose name such Security is registered as the owner thereof for all purposes, whether or not such Security be overdue, and none of the Company, the Guarantors or the Trustee or other
such agent shall be affected by notice to the contrary. 
 (12) Guarantee. Payment of this Security is jointly and
severally and fully and unconditionally guaranteed by the Guarantors that have become and continue to be Guarantors pursuant to the Indenture. Guarantors may be released from their obligations under the Indenture and their Guarantees under the
circumstances specified under the Indenture. 
 (13) No Recourse Against Others. None of the Company’s or any
Guarantor’s past, present or future directors, officers, employees or shareholders, as such, shall have any liability for any of the Company’s or any Guarantor’s obligations under the Indenture or the Securities or for any claim based
on, or in respect or by reason of, such obligations or their creation. By accepting a Security, each Holder waives and releases all such liability. This waiver and release is part of the consideration for the issuance of the Securities. 

(14) Holders’ Compliance with Registration Rights Agreement. Each Holder, by acceptance hereof, acknowledges and agrees to
the provisions of the Registration Rights Agreement in respect of this Security, including the obligations of the Holders with respect to a registration and the indemnification of the Company to the extent provided therein. 

(15) Governing Law. THE INDENTURE, THIS SECURITY AND ANY GUARANTEE SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH
THE LAWS OF THE STATE OF NEW YORK. 
 The Company will furnish to any Holder upon written request and without charge to the
Securityholder a copy of the Indenture which has in it the text of this Security in larger type. Requests may be made to: 
 Aristotle Holding,
Inc. 
 One Express Scripts Way 
 St.
Louis, Missouri 63121 

  
 10 

 ABBREVIATIONS 
 The following abbreviations, when used in the inscription of the face of this Security, shall be construed as though they were written out in full according to applicable laws or regulations: 

TEN COM (= tenant in common) 
 TEN ENT (=
tenants by the entireties (Cust)) 
 JT TEN (= joint tenants with right of survivorship and not as tenants in common) 

UNIF GIFT MIN ACT (= under Uniform Gifts to Minors Act) 
 Additional abbreviations may also be used though not in the above list. 

  
 11 

  
  
 ASSIGNMENT FORM 
 To assign this Security, fill in the form below: 

I or we assign and transfer this Security to 
 (Print or type assignee’s name, address and zip code) 
 (Insert
assignee’s soc. sec. or tax I.D. No.) 
 and irrevocably appoint
                     agent to transfer this Security on the books of the Company. The agent may substitute another to act for him. 

 

									
	  

					
	Date:	 	  
	    		  	Your Signature:	  	  

	
	  

	
	Sign exactly as your name appears on the other side of this Security.

 In connection with any transfer of any of the Securities evidenced by this certificate occurring prior to the expiration
of the period referred to in Rule 144 under the Securities Act after the later of the date of original issuance of such Securities and the last date, if any, on which such Securities were owned by the Company or any Affiliate of the
Company, the undersigned confirms that such Securities are being transferred in accordance with its terms: 
 CHECK ONE BOX BELOW 

 

					
	(1)	  	 ̈	  	pursuant to an effective registration statement under the Securities Act; or
			
	(2)	  	 ̈	  	in the United States to a person whom the seller reasonably believes is a “qualified institutional buyer” (as defined in Rule 144A under the Securities Act) in a
transaction meeting the requirements of Rule 144A; or
			
	(3)	  	 ̈	  	outside the United States in an offshore transaction in accordance with Rule 904 under the Securities Act in compliance with Rule 904 under the Securities Act of 1933, as
amended; or
			
	(4)	  	 ̈	  	pursuant to the exemption from registration under the Securities Act provided by Rule 144.

 Unless one of the boxes is checked, the Trustee will refuse to register any of the Securities evidenced
by this certificate in the name of any person other than the registered 

  
 12 

 
holder thereof; provided, however, that if box (4) is checked, the Trustee shall be entitled to require, prior to registering any such transfer of the Securities, such legal
opinions, certifications and other information as the Company has reasonably requested to confirm that such transfer is being made pursuant to an exemption from, or in a transaction not subject to, the registration requirements of the Securities Act
of 1933, as amended. 
  

	
	 Signature

 Signature Guarantee: 
  

					
	 Signature must be
 guaranteed
	  	                Signature

 Signatures must be guaranteed by an “eligible guarantor institution” meeting the requirements
of the Security Registrar, which requirements include membership or participation in the Security Transfer Agent Medallion Program (“STAMP”) or such other “signature guarantee program” as may be determined by the Security
Registrar in addition to, or in substitution for, STAMP, all in accordance with the Securities Exchange Act of 1934, as amended. 
  

			
	  	 	  
 

  
 13 

 TO BE COMPLETED BY PURCHASER IF (2) ABOVE IS CHECKED. 

The undersigned represents and warrants that it is purchasing this Security for its own account or an account with respect to which it
exercises sole investment discretion and that it and any such account is a “qualified institutional buyer” within the meaning of Rule 144A under the Securities Act of 1933, as amended, and is aware that the sale to it is being made in
reliance on Rule 144A and acknowledges that it has received such information regarding the Company as the undersigned has requested pursuant to Rule 144A or has determined not to request such information and that it is aware that the
transferor is relying upon the undersigned’s foregoing representations in order to claim the exemption from registration provided by Rule 144A. 
  

											
	Dated:	 	  
	 		 		  	  
	  	
						
		 		 		 	Notice:        	  	To be executed by an executive officer	  	

  
 14 

 [TO BE ATTACHED TO GLOBAL SECURITIES] 

SCHEDULE OF INCREASES OR DECREASES IN GLOBAL SECURITY 
 The following increases or decreases in this Global Security have been made: 
  

									
	Date of Exchange	  	 Amount of decrease in

Principal amount of this
 Global Security
	  	 Amount of increase in

Principal amount of this
 Global Security
	  	 Principal amount of this

Global Security following
 such decrease or increase
	  	 Signature of authorized

signatory of Trustee or
 Securities Custodian

		  		  		  		  	

  
 15 

 OPTION OF HOLDER TO ELECT PURCHASE 

If you want to elect to have this Security purchased by the Company pursuant to Section 10.10 of the Indenture, check the
box:   ̈ 

 ̈  If you want to elect to have only part of this Security purchased by the
Company pursuant to Section 10.10 of the Indenture, state the amount in principal amount: $        . 
  

											
		 	Dated:	 		 		  	Your Signature:	  	  

					
		 		 		 		  	 (Sign exactly as your name appears on the
   other side of this Security.)

			
		 	Signature Guarantee:	 	  

 (Signature must be guaranteed) 
 Signatures must be guaranteed by an “eligible guarantor institution” meeting the requirements of the Security Registrar, which requirements include membership or participation in the Security
Transfer Agent Medallion Program (“STAMP”) or such other “signature guarantee program” as may be determined by the Security Registrar in addition to, or in substitution for, STAMP, all in accordance with the Securities Exchange
Act of 1934, as amended. 

  
 16 

 EXHIBIT 2 
 [FORM OF FACE OF EXCHANGE SECURITY 
 OR PRIVATE EXCHANGE
SECURITY] */**/ 
  

	*/	If the Security is to be issued in global form add the Global Securities Legend from Exhibit 1 to the Appendix and the attachment from such Exhibit 1 captioned
“[TO BE ATTACHED TO GLOBAL SECURITIES] - SCHEDULE OF INCREASES OR DECREASES IN GLOBAL SECURITY.” 

	**/	If the Security is a Private Exchange Security issued in a Private Exchange to an Initial Purchaser holding an unsold portion of its initial allotment, add the
Restricted Securities Legend from Exhibit 1 to the Appendix and replace the Assignment Form included in this Exhibit 2 with the Assignment Form included in such Exhibit 1. 

 ARISTOTLE HOLDING, INC. 

3.900% SENIOR NOTE DUE 2022 
  

			
	No.                     	 	Principal Amount (US)$         

 CUSIP NO.
                     
 ISIN
NO.                     

Aristotle Holding, Inc., a corporation organized and existing under the laws of the State of Delaware (herein called the
“Company”, which term includes any successor Person under the Indenture referred to on the reverse hereof), for value received, hereby promises to pay to Cede & Co., or its registered assigns, the principal sum of
                     United States Dollars (U.S.$        ) on February 15, 2022 and to pay
interest thereon, from February 9, 2012, or from the most recent Interest Payment Date to which interest has been paid or duly provided for to but excluding the next Interest Payment Date, which shall be February 15 and August 15 of
each year, commencing August 15, 2012, at the per annum rate of 3.900%, or as such rate may be adjusted pursuant to the terms hereof (the “Security Interest Rate”), until the principal hereof is paid or made available for
payment. 
 The interest so payable, and punctually paid or duly provided for, on any Interest Payment Date will, as provided in
the Indenture, be paid to the Person in whose name this Security is registered at the close of business on the Regular Record Date for such interest, which shall be the day that is 15 days prior to the relevant Interest Payment Date (whether or not
a Business Day). Except as otherwise provided in the Indenture, any such interest not so punctually paid or duly provided for will forthwith cease to be payable to the Holder on such Regular Record Date and may either be paid to the Person in whose
name this Security is registered at the close of business on a Special Record Date for the payment of such Defaulted Interest to be fixed by the Trustee, notice of which shall be given to Holders of Securities not less than 10 days prior to the
Special Record Date, or be paid at any time in any other lawful manner not inconsistent with the requirements of any automated quotation system or securities exchange on which the Securities may be quoted or listed, and upon such notice as may be
required by such exchange, all as more fully provided in the Indenture. Interest will be computed on the basis of a 360-day year comprised of twelve 30-day months. The Company will pay interest on overdue principal at the rate borne by this
Security, and it will pay interest on overdue installments of interest at the same rate to the extent lawful. 
 The Place of
Payment for this Security will be the corporate trust office of the Trustee at 625 Marquette Avenue, 11th Floor, Minneapolis, Minnesota 55479, or as otherwise provided in the Indenture, in such coin or currency of the United States of America as at
the time of payment shall be legal tender for the payment of public and private debts. Payments in respect of the Securities represented by a Global Security (including principal, premium and interest) will be made by wire transfer of immediately
available funds to the accounts specified by the Depository. The Company will make all payments in respect of a Definitive Security (including principal, premium and interest) by mailing a check to the registered address of each Holder thereof as
such address appears on the Security Register; provided, however, that payments on a Definitive Security will be made by wire transfer to a U.S. dollar account maintained by the payee with a bank in the United States if such Holder
elects payment by wire 

  
 2 

 
transfer by giving written notice to the Trustee or the Paying Agent to such effect designating such account no later than 30 days immediately preceding the relevant due date for payment (or
such other date as the Trustee may accept in its discretion). 
 Reference is hereby made to the further provisions of this
Security set forth on the reverse hereof, which further provisions shall for all purposes have the same effect as if set forth at this place. 
 Unless the certificate of authentication hereon has been executed by the Trustee referred to on the reverse hereof by manual signature, this Security shall not be entitled to any benefit under the
Indenture or be valid or obligatory for any purpose. 

  
 3 

 IN WITNESS WHEREOF, the Company has caused this instrument to be duly executed. 

 

			
	ARISTOTLE HOLDING, INC.
		
	By:	 	  

	Name:	 	
	Title:	 	

  

			
	Attest:
		
	By:	 	  

	Name:	 	
	Title:	 	

  
 4 

 CERTIFICATE OF AUTHENTICATION 
 This is one of the Securities of the series designated referred to in the within-mentioned Indenture. 
 Dated: 
  

			
	WELLS FARGO BANK, NATIONAL ASSOCIATION,
	as Trustee
		
	By:	 	  

		 	Authorized Signatory

  
 5 

 [FORM OF REVERSE OF SECURITY] 

(1) Indenture. This Security is one of a duly authorized issue of securities of the Company designated as its “3.900%
Senior Notes due 2022” (herein called the “Securities”), issued under a Seventh Supplemental Indenture, dated as of February 9, 2012, to an indenture, dated as of November 21, 2011 (as it may be amended or
supplemented from time to time in accordance with the terms thereof and herein with the Seventh Supplemental Indenture, collectively, the “Indenture”), between the Company, the Guarantors and Wells Fargo Bank, National Association,
as Trustee (herein called the “Trustee,” which term includes any successor trustee under the Indenture), to which reference is hereby made for a statement of the respective rights, limitations of rights, duties and immunities
thereunder of the Company, the Guarantors, the Trustee and the Holders of the Securities and of the terms upon which the Securities are, and are to be, authenticated and delivered. The aggregate principal amount of Initial Securities Outstanding at
any time may not exceed $1,000,000,000 in aggregate principal amount, except for Securities issued, authenticated and delivered upon registration or transfer of, or in exchange for, or in lieu of, other Securities pursuant to Sections 3.4, 3.5, 3.6,
9.6 or 11.7 of the Base Indenture and except for any Securities which, pursuant to Section 3.3 of the Base Indenture, are deemed never to have been authenticated and delivered. The Seventh Supplemental Indenture pursuant to which this Security
is issued provides that Additional Securities may be issued thereunder, if certain conditions are met. The Initial Securities issued pursuant to the Seventh Supplemental Indenture and all Exchange Securities or Private Exchange Securities issued in
exchange therefor will be treated as a single class for all purposes under the Indenture. 
 The Indenture contains covenants
that limit the ability of the Company and any Restricted Subsidiary to create liens on assets and to engage in sale/leaseback transactions. The Indenture also contains covenants that limit the ability of the Company and, prior to the consummation of
the Mergers, of Express Scripts to consolidate, merge or transfer all or substantially all of their respective assets. These covenants are subject to important exceptions and qualifications. 

All terms used in this Security which are defined in the Indenture (including in the Appendix thereto) shall have the meanings assigned
to them in the Indenture. In the event of a conflict or inconsistency between this Security and the Indenture, the provisions of the Indenture shall govern. 
 (2) Optional Redemption. At any time prior to Maturity, the Company may at its option redeem all or a part of the Securities upon not more than 60 nor less than 30 days prior notice, at a
Redemption Price equal to the greater of: (i) 100% of the aggregate principal amount of any Securities being redeemed, plus accrued and unpaid interest on the Securities to the Redemption Date; or (ii) the sum of the present values of the
remaining scheduled payments of principal of and interest on the Securities to be redeemed (exclusive of unpaid interest accrued thereon to the Redemption Date) discounted to the Redemption Date on a semi-annual basis (assuming a 360-day year
comprised of twelve 30-day months) at the Treasury Rate plus 40 basis points, plus unpaid interest on the Securities to be redeemed, accrued to the Redemption Date. 

  
 6 

 (3) Mandatory Redemption. Except as provided in Sections 4 and 5 below, the Company
is not required to make mandatory redemption or sinking fund payments with respect to the Securities. 
 (4) Special
Mandatory Redemption. If for any reason (i) the Mergers are not consummated on or prior to the Special Mandatory Redemption Triggering Date or (ii) the Merger Agreement is terminated at any time prior thereto, then the Company shall
redeem all the Securities on the Special Mandatory Redemption Date at a price equal to 101% of the aggregate accreted principal amount of such Security, plus accrued and unpaid interest from the date of original issuance to, but excluding, the
Special Mandatory Redemption Date (subject to the right of Holders on the relevant Regular Record Date to receive interest due on the relevant Interest Payment Date). 
 (5) Change of Control Triggering Event. In the event of a Change of Control Triggering Event, the Holders may require the Company to purchase for cash all or a portion of their Securities at a
purchase price equal to 101% of the aggregate principal amount of the Securities repurchased, plus accrued and unpaid interest, if any, pursuant to the provisions of Section 10.10 of the Base Indenture. 

(6) Global Security. If this Security is a Global Security, then the transfer and exchange of this Security or beneficial
interests herein shall be effected through the Depository in accordance with the Indenture (including applicable restrictions on transfer set forth therein, if any) and the procedures of the Depository therefor. The Security Registrar shall make an
adjustment on its records to reflect such deposit or withdrawal in accordance with the Depository’s Procedures. 
 (7)
Defaults and Remedies. If an Event of Default with respect to this Security occurs and is continuing, the principal of and any unpaid premium and interest on (or, if this Security is an Original Issue Discount Security, such portion of the
principal amount of such Securities as may be specified in the terms thereof) all outstanding securities of this series, may be declared due and payable in the manner and with the effect provided in the Indenture. The Holders of at least a majority
in principal amount of the Outstanding Securities may rescind or annul that acceleration if all Events of Default with respect to the Securities other than the non-payment of accelerated principal have been cured or waived as provided in the
Indenture. 
 As provided in and subject to the provisions of the Indenture, the Holder of this Security shall not have the
right to institute any proceeding with respect to the Indenture or for the appointment of a receiver or trustee or for any other remedy thereunder, unless such Holder shall have previously given the Trustee written notice of a continuing Event of
Default, and, among other things, the Holders of not less than 25% in aggregate principal amount of the Outstanding Securities shall have made a written request to the Trustee to pursue a remedy in respect of such Event of Default as Trustee. The
foregoing shall not apply to any suit instituted by the Holder of this Security for the enforcement of any amounts due on the Securities on or after the respective due dates expressed herein. 

(8) Discharge and Defeasance. Subject to certain conditions, the Company at any time shall be entitled to terminate some or all of
the Company’s and the Guarantors’ 

  
 7 

 
obligations under the Securities, the Guarantees and the Indenture if the Company deposits with the Trustee money or U.S. Government Obligations for the payment of principal and interest on the
Securities to redemption or maturity, as the case may be. 
 (9) Amendment, Supplement and Waiver. The Indenture permits,
with certain exceptions as therein provided, the amendment thereof and the modification of the rights and obligations of the Company and the rights of the Holders of the Securities under the Indenture at any time by the Company and the Trustee with
the written consent of the Holders of at least a majority in aggregate principal amount of the Outstanding Securities. The provisions relating to the Special Mandatory Redemption set forth in Sections 4.2 and 4.3 of the Seventh Supplemental
Indenture may not be modified or waived without the written consent of 66 2/3% in aggregate principal amount of the Outstanding Securities. The Indenture also contains provisions permitting the Holders of specified percentages in principal amount of
the Outstanding Securities, on behalf of the Holders of all such Securities, to waive compliance by the Company with certain provisions of the Indenture and certain past defaults under the Indenture and their consequences. Any such consent or waiver
by the Holder of this Security shall be conclusive and binding upon such Holder and upon all future Holders of this Security and of any Security issued upon the registration of transfer hereof or in exchange herefor or in lieu hereof whether or not
notation of such consent or waiver is made upon this Security or such other Security. Certain modifications or amendments to the Indenture require the consent of the Holder of each Outstanding Security affected. 

Notwithstanding any other provision of the Indenture or this Security, the Holder of this Security shall have the right, which is
absolute and unconditional, to receive payment of the principal of and any premium and (subject to Section 3.7 of the Base Indenture) interest on any such Security on the Stated Maturity date expressed herein (or, in the case of redemption, on
the Redemption Date) and to institute suit for the enforcement of any such payment, and such rights shall not be impaired without the consent of such Holder. 
 (10) Denomination, Registration and Transfer. The Securities are in registered form without coupons in minimum denominations of $2,000 principal amount and integral multiples of $1,000 in excess
thereof. As provided in the Indenture and subject to certain limitations therein set forth, this Security is transferable only upon surrender of this Security for registration of transfer. Upon surrender for registration of transfer of this Security
at the office or agency of the Company in a Place of Payment for this Security, the Company, if the requirements of the Indenture are met, shall execute, and the Trustee shall authenticate and deliver, in the name of the designated transferee or
transferees, one or more new Securities of authorized denominations and of like tenor and aggregate principal amount, and having endorsed thereon a Guarantee executed by the Guarantors. 

If the requirements of this Indenture are met, then, at the option of the Holder, Securities may be exchanged for other Securities, of
any authorized denominations and of like tenor and aggregate principal amount, upon surrender of the Securities to be exchanged at such office or agency. Whenever any Securities are so surrendered for exchange, the Company shall execute, and the
Trustee shall authenticate and deliver, the Securities which the Holder making the exchange is entitled to receive, and having endorsed thereon a Guarantee executed by the Guarantor. No service charge shall be made for any such registration of
transfer or exchange, but the Company may require payment of a sum sufficient to cover any tax or other governmental charge that may be imposed in connection therewith. 

  
 8 

 Prior to due presentment of this Security for registration of transfer, the Company, the
Guarantors, the Trustee and any agent of the Company, the Guarantors or the Trustee may treat the Person in whose name such Security is registered as the owner thereof for all purposes, whether or not such Security be overdue, and none of the
Company, the Guarantors or the Trustee or other such agent shall be affected by notice to the contrary. 
 (11)
Guarantee. Payment of this Security is jointly and severally and fully and unconditionally guaranteed by the Guarantors that have become and continue to be Guarantors pursuant to the Indenture. Guarantors may be released from their
obligations under the Indenture and their Guarantees under the circumstances specified under the Indenture. 
 (12) No
Recourse Against Others. None of the Company’s or any Guarantor’s past, present or future directors, officers, employees or shareholders, as such, shall have any liability for any of the Company’s or any Guarantor’s
obligations under the Indenture or the Securities or for any claim based on, or in respect or by reason of, such obligations or their creation. By accepting a Security, each Holder waives and releases all such liability. This waiver and release is
part of the consideration for the issuance of the Securities. 
 (13) [Holders’ Compliance with
Registration Rights Agreement. Each Holder, by acceptance hereof, acknowledges and agrees to the provisions of the Registration Rights Agreement in respect of this Security, including the obligations of the Holders with respect to a registration
and the indemnification of the Company to the extent provided therein.]1 
 (14) Governing Law. THE INDENTURE, THIS SECURITY AND ANY
GUARANTEE SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK. 
 The Company will
furnish to any Holder upon written request and without charge to the Securityholder a copy of the Indenture which has in it the text of this Security in larger type. Requests may be made to: 
 Aristotle Holding, Inc. 
 One Express Scripts Way 

St. Louis, Missouri 63121 

ABBREVIATIONS 

The following abbreviations, when used in the inscription of the face of this Security, shall be construed as though they were written
out in full according to applicable laws or regulations: 
  

	1 	 Delete if this is not a Private Exchange Security. 

  
 9 

 TEN COM (= tenant in common) 
 TEN ENT (= tenants by the entireties (Cust)) 
 JT TEN (= joint tenants with right of survivorship
and not as tenants in common) 
 UNIF GIFT MIN ACT (= under Uniform Gifts to Minors Act) 

Additional abbreviations may also be used though not in the above list. 

  
 10 

 ASSIGNMENT FORM 
 To assign this Security, fill in the form below: 
 I or we assign and transfer this Security to

 (Print or type assignee’s name, address and zip code) 

(Insert assignee’s soc. sec. or tax I.D. No.) 
 and irrevocably appoint                      agent to transfer this Security on the books of the
Company. The agent may substitute another to act for him. 
  

									
	  

					
	Date:	 		    		  	Your Signature:	  	  

	
	  

	
	Sign exactly as your name appears on the other side of this Security.

  
 11 

 OPTION OF HOLDER TO ELECT PURCHASE 

If you want to elect to have this Security purchased by the Company pursuant to Section 10.10 of the Indenture, check the
box:   ̈ 

 ̈  If you want to elect to have only part of this Security purchased by the
Company pursuant to Section 10.10 of the Indenture, state the amount in principal amount: $        . 
  

											
		 	Dated:	 		 		  	Your Signature:	  	  

					
		 		 		 		  	 (Sign exactly as your name appears on the
   other side of this Security.)

			
		 	Signature Guarantee:	 	  

 (Signature must be guaranteed) 
 Signatures must be guaranteed by an “eligible guarantor institution” meeting the requirements of the Security Registrar, which requirements include membership or participation in the Security
Transfer Agent Medallion Program (“STAMP”) or such other “signature guarantee program” as may be determined by the Security Registrar in addition to, or in substitution for, STAMP, all in accordance with the Securities Exchange
Act of 1934, as amended. 

  
 12 

 EXHIBIT 3 
 FORM OF GUARANTEE 
 For value received, each of the Guarantors (which term
includes any successor Person under the Indenture) has jointly and severally and fully and unconditionally guaranteed, to the extent set forth in the Indenture, among the Company, the Guarantors and the Trustee and subject to the provisions in the
Indenture, (a) the due and punctual payment in full when due of the principal of, premium, if any, and interest on the Securities and all other amounts due and payable under the Indenture and the Securities by the Company and (b) in case
of any extension of time of payment or renewal of any Obligations (with or without notice to the Guarantor), that the same will be promptly paid in full when due or performed in accordance with the terms of the extension or renewal, whether at
Stated Maturity, by acceleration or otherwise. The obligations of the Guarantors to the Holders of Securities and to the Trustee pursuant to the Guarantee and the Indenture are expressly set forth in Article XIII of the Indenture and reference is
hereby made to the Indenture for the precise terms of the Guarantee, including provisions for the release thereof. Each Holder of a Security, by accepting the same, (a) agrees to and shall be bound by such provisions and (b) appoints the
Trustee attorney-in-fact of such Holder for the purpose of such provisions. 
  

			
	[NAME OF GUARANTOR(S)]
		
	By:	 	  

	Name:	 	  

	Title:Purchase Agreement, dated February 6, 2012

 Exhibit 10.1 
 EXECUTION COPY 
 ARISTOTLE HOLDING, INC. 

$1,000,000,000 2.100% Senior Notes Due 2015 
 $1,500,000,000 2.650% Senior Notes Due 2017 
 $1,000,000,000 3.900% Senior
Notes Due 2022 
 PURCHASE AGREEMENT 
 February 6, 2012 
 CITIGROUP GLOBAL MARKETS
INC., 
 388 Greenwich Street, 
 New York, N.Y. 10013 
 CREDIT SUISSE SECURITIES (USA)
LLC, 
 Eleven Madison Avenue, 
 New York, N.Y. 10010-3629 
 As representatives (the “Representatives”) of the
Several Initial Purchasers 
 Dear Sirs: 
 1. Introductory. Aristotle Holding, Inc., a Delaware corporation (the “Company”) and a wholly owned subsidiary of Express Scripts, Inc., a Delaware corporation (“Express
Scripts”), agrees with the several initial purchasers named in Schedule A hereto (the “Initial Purchasers”) to issue and sell to the Initial Purchasers $1,000,000,000 aggregate principal amount of its 2.100% Senior Notes
due 2015 (the “2015 Notes”), $1,500,000,000 aggregate principal amount of its 2.650% Senior Notes due 2017 (the “2017 Notes”) and $1,000,000,000 aggregate principal amount of its 3.900% Senior Notes due 2022 (the
“2022 Notes” and, together with the 2015 Notes and the 2017 Notes, the “Offered Securities”). The Offered Securities will be unconditionally guaranteed (the “Guarantees”) by the Closing Date
Guarantors (as defined below) and any other entity that becomes a guarantor of the Offered Securities following the Closing Date (as defined below), including the Merger Date Guarantors (as defined below), pursuant to the terms of the Indenture (as
defined below). The Offered Securities shall be issued under an indenture, dated as of November 21, 2011 (the “Base Indenture”), and supplemented by supplemental indentures (each, a “Supplemental Indenture”
and, collectively, the “Supplemental Indentures”) to be dated as of the Closing Date, among the Company, each of the entities listed on Schedule B-1 hereto (collectively, the “Closing Date Guarantors”) and Wells
Fargo Bank, National Association, as Trustee (the Base Indenture, as supplemented by the Supplemental Indentures entered into on the Closing Date and as may be supplemented from time to time after the Closing Date, the “Indenture”).

 Pursuant to the Agreement and Plan of Merger dated as of July 20, 2011, as amended by Amendment No. 1 thereto on
November 7, 2011 (the “Merger Agreement”), by and among Express Scripts, Medco Health Solutions, Inc., a Delaware corporation (“Medco”), the Company, Aristotle Merger Sub, Inc., a Delaware corporation and a
wholly owned subsidiary of the Company (“Aristotle Merger Sub”), and Plato Merger Sub, Inc., a Delaware Corporation and a wholly owned subsidiary of the Company (“Plato Merger Sub”), Aristotle Merger Sub will merge
with and into Express Scripts (the “Express Scripts Merger”), with Express Scripts as the surviving corporation, and Plato Merger Sub will merge with and into Medco (collectively with the Express Scripts Merger, the
“Mergers”), with Medco as the surviving corporation. As a result of the Mergers, Medco and Express Scripts will become wholly owned subsidiaries of the Company. The date on which the Mergers are consummated is referred to herein as
the “Merger Date”, and Medco and the subsidiaries of Medco listed on Schedule B-2 hereto are referred to herein as the “Merger Date Guarantors”. 

On the Merger Date Medco will, and within 60 days following the Merger Date each other Merger Date Guarantor will, enter into (a) a
joinder agreement to this Agreement, the form of which is attached as 

 
Schedule H hereto (each, a “Joinder Agreement” and collectively, the “Joinder Agreements”), (b) a Supplemental Indenture, pursuant to which such Merger Date
Guarantor will become a party to the Indenture and (c) a counterpart to each Registration Rights Agreement (as defined below) in the form attached thereto as Exhibit A (each, a “Registration Rights Joinder” and, collectively,
the “Registration Rights Joinders”). Upon the execution and delivery of a Joinder Agreement by a Merger Date Guarantor, the representations, warranties and agreements of such Merger Date Guarantor set forth herein shall become
effective pursuant to the terms of such Joinder Agreement, and each such Merger Date Guarantor will, without further action by any person, become a party to this Agreement. References to the “Guarantors” refer to (x) prior to
the consummation of the Mergers and the execution and delivery of any Joinder Agreements and Supplemental Indentures by any Merger Date Guarantors, the Closing Date Guarantors and (y) following the consummation of the Mergers and the execution
and delivery of a Joinder Agreement and Supplemental Indenture by a Merger Date Guarantor, the Closing Date Guarantors and such Merger Date Guarantor. 
 The Offered Securities will be offered and sold to the Initial Purchasers pursuant to an exemption from the registration requirements of the Securities Act (as defined below). The Offered Securities may
be sold by the Initial Purchasers or their respective affiliates pursuant to Regulation S under the Securities Act (“Regulation S”) to investors outside of the United States that are not U.S. persons (as defined in Regulation S) and
pursuant to Rule 144A under the Securities Act (“Rule 144A”) to qualified institutional buyers in the United States or qualified institutional buyers that are U.S. persons. 

The holders of each series of the Offered Securities will be entitled to the benefits of a Registration Rights Agreement dated as of the
Closing Date among the Company, the Closing Date Guarantors and the Representatives (each, a “Registration Rights Agreement” and, collectively, the “Registration Rights Agreements”). Following the execution of the
Registration Rights Joinders by a Merger Date Guarantor, such Merger Date Guarantor shall be bound by all obligations of the “Guarantors” and the “Company” under the Registration Rights Agreements. Pursuant to each Registration
Rights Agreement, the Company and the Guarantors shall use commercially reasonable efforts to cause an exchange offer registration statement to become effective under the Securities Act and to conduct a registered exchange offer for the applicable
series of the Offered Securities, or to use their commercially reasonable efforts to cause to become effective a shelf registration statement filed with the Commission registering the resale of the applicable series of the Offered Securities under
the Securities Act. 
 2. Representations and Warranties of the Company and the Guarantors. The Company and each Closing
Date Guarantor and, upon execution and delivery of a Joinder Agreement in the case of each of clauses (d), (f), (o), (p), (t), (v), (bb), (cc) and (dd) of this Section 2, each Merger Date Guarantor, jointly and severally represents and warrants
to, and agrees with, the Initial Purchasers that: 
 (a) Offering Circulars; Certain Defined Terms. The
Company has prepared or will prepare a Preliminary Offering Circular and a Final Offering Circular. 
 For
purposes of this Agreement: 
 “Applicable Time” means 5:00 p.m. (Eastern time) on the date of
this Agreement. 
 “Closing Date” has the meaning defined in Section 3 hereof. 

“Commission” means the Securities and Exchange Commission. 

“Exchange Act” means the Securities Exchange Act of 1934, as amended. 

“Final Offering Circular” means the final offering circular (including any information incorporated by
reference therein) relating to the Offered Securities to be offered by the Initial Purchasers that discloses the offering price and other final terms of the Offered Securities and is dated as of the date of this Agreement (even if finalized and
issued subsequent to the date of this Agreement). 

  
 2 

 “Free Writing Communication” means a written communication
(as such term is defined in Rule 405) that constitutes an offer to sell or a solicitation of an offer to buy the Offered Securities and is made by means other than the Preliminary Offering Circular or the Final Offering Circular. 

“General Disclosure Package” means the Preliminary Offering Circular together with any Issuer Free
Writing Communication existing at the Applicable Time and the information which is intended for general distribution to prospective investors, as evidenced by its being specified in Schedule C hereto. 

“Issuer Free Writing Communication” means a Free Writing Communication prepared by or on behalf of the
Company, used or referred to by the Company or containing a description of the final terms of the Offered Securities or of their offering, in the form retained in the Company’s records. 

“Order” means any judgment, order, injunction, decree, writ, stipulation, ruling, determination, award,
permit or license of any governmental entity or any arbitrator. 
 “Preliminary Offering
Circular” means the preliminary offering circular (including any information incorporated by reference therein), dated February 6, 2012, relating to the Offered Securities to be offered by the Initial Purchasers. 

“Rules and Regulations” means the rules and regulations of the Commission. 

“Securities Act” means the Securities Act of 1933, as amended. 

“Securities Laws” means, collectively, the Sarbanes-Oxley Act of 2002, as amended
(“Sarbanes-Oxley”), the Securities Act, the Exchange Act, the Rules and Regulations, the auditing principles, rules, standards and practices applicable to auditors of “issuers” (as defined in Sarbanes-Oxley) promulgated or
approved by the Public Company Accounting Oversight Board and the rules of the NASDAQ Stock Market. 

“Supplemental Marketing Material” means any Issuer Free Writing Communication other than any Issuer Free
Writing Communication specified in Schedule C hereto. Supplemental Marketing Materials include, but are not limited to, any electronic Bloomberg roadshow slides and the accompanying audio recording. 

“Trust Indenture Act” means the Trust Indenture Act of 1939. 

Unless otherwise specified, a reference to a “rule” is to the indicated rule under the Securities Act. 

(b) Disclosure. As of its date and as of the Closing Date, the Final Offering Circular will not include any untrue
statement of a material fact or omit to state any material fact required to be stated therein or necessary to make the statements therein, in the light of the circumstances under which they were made, not misleading. At the Applicable Time, and as
of the Closing Date, neither (i) the General Disclosure Package nor (ii) any individual Supplemental Marketing Material, when considered together with the General Disclosure Package, included, or will include, any untrue statement of a
material fact or omitted, or will omit, to state any material fact required to be stated therein or necessary to make the statements therein, in the light of the circumstances under which they were made, not misleading. The preceding two sentences
do not apply to statements in or omissions from the Preliminary Offering Circular, the Final Offering Circular, the General Disclosure Package or any Supplemental Marketing Material in reliance upon and in conformity with written information
furnished to the Company by any Initial Purchaser through the Representatives specifically for use therein, it being understood and agreed that the only such information furnished by any Initial Purchaser consists of the information described as
such in Section 8(b) hereof. The Annual Reports on Form 10-K most recently filed by each of Express Scripts and Medco with the Commission, as amended by the Form 8-K filed by Express Scripts on October 25, 2011, and all subsequent reports
which have been filed by 

  
 3 

 
Express Scripts or Medco with the Commission and incorporated by reference in the Preliminary Offering Circular or the Final Offering Circular conformed in all material respects to the
requirements of the Exchange Act and the Rules and Regulations at the time each such document was filed with the Commission. It is understood that the representations and warranties of the Company and the Closing Date Guarantors in this paragraph
(b) with respect to the Annual Report on Form 10-K most recently filed by Medco with the Commission and all subsequent reports which have been filed by Medco with the Commission and incorporated by reference in the Preliminary Offering Circular
or the Final Offering Circular are made to the knowledge of the Company and each Closing Date Guarantor. 
 (c)
Good Standing of the Company. The Company (i) has been duly incorporated and is existing and in good standing under the laws of the State of Delaware, with power and authority (corporate and other) to own its properties and conduct its
business as described in the General Disclosure Package and (ii) is duly qualified to do business as a foreign corporation in good standing in all other jurisdictions in which its ownership or lease of property or the conduct of its business
requires such qualification, except in the case of clause (ii) where the failure to so qualify would not result in a material adverse change in the condition, financial or otherwise, or in the earnings, business, affairs or business prospects
of either (x) Express Scripts and its subsidiaries, considered as one enterprise, or (y) the Company and its subsidiaries, considered as one enterprise after giving pro forma effect to the Mergers, in each case, whether or not arising in
the ordinary course of business (a “Material Adverse Effect”). 
 (d) Guarantor Good
Standing. Each Closing Date Guarantor and each Merger Date Guarantor (i) has been duly organized and is existing and in good standing under the laws of the jurisdiction of its organization, with power and authority (corporate and other) to
own its properties and conduct its business as described in the General Disclosure Package and (ii) is duly qualified to do business as a foreign corporation, limited partnership, limited liability company or other entity in good standing,
where applicable, in all other jurisdictions in which its ownership or lease of property or the conduct of its business requires such qualification, except in the case of clause (ii) where the failure to so qualify would not have a Material
Adverse Effect; and all of the issued and outstanding capital stock of each Closing Date Guarantor and each Merger Date Guarantor has been duly authorized and validly issued and is fully paid and nonassessable; and the capital stock of each Closing
Date Guarantor and each Merger Date Guarantor is owned free from liens, encumbrances and defects (it being understood that the representations and warranties of the Company and the Closing Date Guarantors in this paragraph (d) with respect to
the Merger Date Guarantors are made to the knowledge of the Company and each Closing Date Guarantor). 
 (e)
Execution and Delivery of Base Indenture; Supplemental Indentures; Registration Rights Agreements; Guarantees; Offered Securities; Exchange Securities. The Base Indenture, the Supplemental Indentures to be dated the Closing Date and the
Registration Rights Agreements have been duly authorized by the Company and each Closing Date Guarantor; on the Closing Date (when the Offered Securities are delivered and paid for pursuant to this Agreement), the Base Indenture, the Supplemental
Indentures to be dated the Closing Date and the Registration Rights Agreements will have been duly executed and delivered by the Company and each Closing Date Guarantor and will constitute valid and legally binding obligations of the Company and
each Closing Date Guarantor, enforceable in accordance with their terms, subject to bankruptcy, insolvency, fraudulent transfer, reorganization, moratorium and similar laws of general applicability relating to or affecting creditors’ rights and
to general equity principles (and, in the case of the Registration Rights Agreements, except as rights to indemnification and contribution may be limited under applicable law); the Guarantees to be provided by the Closing Date Guarantors have been
duly authorized by each Closing Date Guarantor; the Offered Securities have been duly authorized by the Company and will have been duly executed, authenticated and issued (assuming that the Offered Securities have been authenticated in the manner
provided in the Indenture by the Trustee) on the Closing Date in accordance with the provisions of the Indenture and, when delivered to and paid for on the Closing Date pursuant to this Agreement, the Offered Securities and the Guarantees of the
Closing Date Guarantors will constitute valid and legally binding obligations of the Company and each Closing Date Guarantor, as applicable, enforceable 

  
 4 

 
in accordance with their terms, subject to bankruptcy, insolvency, fraudulent transfer, reorganization, moratorium and similar laws of general applicability relating to or affecting
creditors’ rights and to general equity principles; the Offered Securities conform to the description of such Offered Securities contained in the General Disclosure Package and will conform to the description of such Offered Securities in the
Final Offering Circular; and the Exchange Securities (as defined in each Registration Rights Agreement) and the guarantees thereof by each Closing Date Guarantor have been duly authorized by the Company and each Closing Date Guarantor and, when the
Exchange Securities have been duly executed and authenticated in accordance with the provisions of the Indenture and delivered in accordance with the terms of the Registered Exchange Offers (as defined in each Registration Rights Agreement), the
Exchange Securities and the guarantees thereof by the Closing Date Guarantors will constitute valid and legally binding obligations of the Company and each Closing Date Guarantor, as applicable, enforceable in accordance with their terms, subject to
bankruptcy, insolvency, fraudulent transfer, reorganization, moratorium and similar laws of general applicability relating to or affecting creditors’ rights and to general equity principles. 

(f) Execution and Delivery of Joinder Agreements; Supplemental Indentures; Registration Rights Joinders;
Guarantees. (i) On the Merger Date, a Supplemental Indenture (including the Guarantees to be provided thereby), a Joinder Agreement and a Registration Rights Joinder with respect to each Registration Rights Agreement will have been duly
authorized, executed and delivered by Medco, and such Joinder Agreement, this Agreement, such Supplemental Indenture, the Indenture, each Registration Rights Joinder, each Registration Rights Agreement and the Guarantees of Medco will constitute
valid and legally binding obligations of Medco, enforceable in accordance with their terms, subject to bankruptcy, insolvency, fraudulent transfer, reorganization, moratorium and similar laws of general applicability relating to or affecting
creditors’ rights and to general equity principles (and, in the case of the Registration Rights Agreements, except as rights to indemnification and contribution may be limited by applicable law); (ii) on the date that each other Merger
Date Guarantor is required to guarantee the Offered Securities pursuant to the terms of the Indenture, a Supplemental Indenture (including the Guarantees to be provided thereby), a Joinder Agreement and a Registration Rights Joinder with respect to
each Registration Rights Agreement will have been duly authorized, executed and delivered by the other Merger Date Guarantors, and such Joinder Agreement, this Agreement, such Supplemental Indenture, the Indenture, each Registration Rights Joinder,
each Registration Rights Agreement and the Guarantees of the other Merger Date Guarantors will constitute valid and legally binding obligations of each of the other Merger Date Guarantors, enforceable in accordance with their terms, subject to
bankruptcy, insolvency, fraudulent transfer, reorganization, moratorium and similar laws of general applicability relating to or affecting creditors’ rights and to general equity principles (and, in the case of the Registration Rights
Agreements, except as rights to indemnification and contribution may be limited by applicable law); and (iii) prior to their issuance, the guarantees of the Exchange Securities to be provided by the Merger Date Guarantors will have been duly
authorized by each Merger Date Guarantor, and when the Exchange Securities have been executed and authenticated in accordance with the provisions of the Indenture and delivered in accordance with the terms of the Registered Exchange Offer, the
guarantees of the Exchange Securities by the Merger Date Guarantors will constitute valid and legally binding obligations of each Merger Date Guarantor, enforceable in accordance with their terms, subject to bankruptcy, insolvency, fraudulent
transfer, reorganization, moratorium and similar laws of general applicability relating to or affecting creditors’ rights and to general equity principles. 
 (g) Trust Indenture Act. On the Closing Date, the Indenture will conform in all material respects to the requirements of the Trust Indenture Act and the Rules and Regulations applicable to an
indenture which is qualified thereunder. 
 (h) No Registration Rights. There are no contracts, agreements
or understandings (other than the Registration Rights Agreements, the Registration Rights Joinders and the registration rights agreements and registration rights joinders relating to the 2.750% Senior Notes due 2014, the 3.500% Senior Notes due
2016, the 4.750% Senior Notes due 2021 and the 6.125% Senior Notes due 2041, in each case, issued by the Company on November 21, 2011) between the 

  
 5 

 
Company, any Closing Date Guarantor or any Merger Date Guarantor, on the one hand, and any other person, on the other hand, granting such person the right to require the Company, any Closing Date
Guarantor or any Merger Date Guarantor to file a registration statement under the Securities Act with respect to any securities of the Company, any Closing Date Guarantor or any Merger Date Guarantor or to require the Company, any Closing Date
Guarantor or any Merger Date Guarantor to include such securities with the securities and guarantees registered pursuant to any Registration Statement (as defined in the Registration Rights Agreements) (it being understood that the representations
and warranties of the Company and the Closing Date Guarantors in this paragraph (h) with respect to the Merger Date Guarantors are made to the knowledge of the Company and each Closing Date Guarantor). 

(i) Absence of Further Requirements. No consent, approval, authorization, or order of, or filing or registration
with, any governmental agency or body or any court is necessary or required for (i) the execution, delivery or performance by the Company or the Guarantors, as applicable, of their obligations under this Agreement, the Joinder Agreements, the
Indenture, the Registration Rights Joinders, the Registration Rights Agreements, the Offered Securities, the Guarantees, the Exchange Securities and the guarantees thereof or the consummation by the Company or the Guarantors of the transactions
contemplated by this Agreement, the Indenture or the Registration Rights Agreements, except such as have been obtained or made, such as may be required under state securities or blue sky laws in connection with the purchase and distribution of the
Offered Securities by the Initial Purchasers and such as may be required under the Securities Act, the Trust Indenture Act and state securities or blue sky laws in connection with the transactions contemplated by the Registration Rights Agreements
or (ii) the execution, delivery or performance by the Company, the Closing Date Guarantors or the Merger Date Guarantors of the Merger Agreement or the consummation of the Mergers, except as disclosed in the General Disclosure Package or as set
forth in Section 3.4(a) and 4.5(a) of the Merger Agreement (it being understood that the representations and warranties of the Company and the Closing Date Guarantors in this paragraph (i) with respect to the Merger Date Guarantors are
made to the knowledge of the Company and each Closing Date Guarantor). 
 (j) Title to Property. The
Company, each Closing Date Guarantor and each Merger Date Guarantor has good and marketable title to all of their respective real properties and good title to their respective personal properties, in each case free and clear of any security
interest, mortgage, pledge, lien, encumbrance, claim or equitable right except (A) as disclosed in the General Disclosure Package or (B) as does not have a Material Adverse Effect and does not interfere with the use made and proposed to be
made of such property by the Company and each Guarantor considered as one enterprise; and all of the leases and subleases of the Company and each Guarantor considered as one enterprise, and under which the Company or any Guarantor holds properties
described in the General Disclosure Package, are in full force and effect, except such failures to be in full force and effect that would not, individually or in the aggregate, result in a Material Adverse Effect (it being understood that the
representations and warranties of the Company and the Closing Date Guarantors in this paragraph (j) with respect to the Merger Date Guarantors are made to the knowledge of the Company and each Closing Date Guarantor). 

(k) Absence of Defaults and Conflicts Resulting from Transaction. The execution, delivery and performance by the
Company and each of the Guarantors, as applicable, of the Indenture, this Agreement, the Registration Rights Agreements, the Joinder Agreements and the Registration Rights Joinders and compliance with the terms and provisions thereof, the
consummation of the transactions herein and therein contemplated (including the use of proceeds from the sale of the Offered Securities, the Mergers and the entry into the Merger Agreement), the issuance and sale of the Offered Securities and the
issuance of the Guarantees and compliance with the terms and provisions thereof, and the issuance and sale of the Exchange Securities and the related guarantees and compliance with the terms and provisions thereof will not, in each case, result in a
breach or violation of any of the terms and provisions or result in the imposition of any lien, charge or encumbrance upon any property or assets of the Company or any Guarantor pursuant to (i) the charter or by-laws or similar organizational
documents of the Company or any Guarantor, (ii) any statute, rule, regulation or order of any governmental agency or body or any 

  
 6 

 
court, domestic or foreign, having jurisdiction over the Company or any Guarantor or any of their properties or (iii) any agreement or instrument to which the Company or any Guarantor is a
party or by which the Company or any Guarantor is bound or to which any of the properties of the Company or any Guarantor is subject, except in the case of clauses (ii) and (iii), for such breaches, defaults, liens, charges or encumbrances that
would not, individually or in the aggregate, result in a Material Adverse Effect (it being understood that the representations and warranties of the Company and the Closing Date Guarantors in this paragraph (k) with respect to the Merger Date
Guarantors are made to the knowledge of the Company and each Closing Date Guarantor). 
 (l) Absence of
Existing Defaults and Conflicts. None of the Company, any Closing Date Guarantor or any Merger Date Guarantor is in violation of its respective organizational documents or in default (or with the giving of notice or lapse of time would be in
default) under any existing obligation, agreement, covenant or condition contained in any indenture, loan agreement, mortgage, lease or other agreement or instrument to which any of them is a party or by which any of them is bound or to which any of
the properties of any of them is subject, except such defaults that would not, individually or in the aggregate, result in a Material Adverse Effect (it being understood that the representations and warranties of the Company and the Closing Date
Guarantors in this paragraph (l) with respect to the Merger Date Guarantors are made to the knowledge of the Company and each Closing Date Guarantor). 
 (m) Authorization of this Agreement. This Agreement has been duly authorized, executed and delivered by the Company and each Closing Date Guarantor. 

(n) Possession of Licenses and Permits. The Company, each Closing Date Guarantor and each Merger Date Guarantor
(A) possesses, and is in compliance with the terms of, all adequate certificates, authorizations, franchises, licenses and permits (including certificates of need, licenses, pharmacy licenses, Medicare provider numbers, accreditations and other
similar documentation or approvals of any local health departments or any governmental authority) (collectively, “Licenses”) necessary or material to the conduct of the business now conducted except where the failure to possess any
such License would not result in a Material Adverse Effect and (B) have not received any notice of proceedings relating to the revocation or modification of any Licenses that, if determined adversely to the Company or such Guarantor, would
individually or in the aggregate have a Material Adverse Effect (it being understood that the representations and warranties of the Company and the Closing Date Guarantors in this paragraph (n) with respect to the Merger Date Guarantors are
made to the knowledge of the Company and each Closing Date Guarantor). 
 (o) Accurate Disclosure. The
statements in the General Disclosure Package and the Final Offering Circular under the headings “Description of the Notes”, “Description of Other Indebtedness”, “The Mergers—The Merger Agreement,” “The
Mergers—Financing Transactions” and “Material United States Federal Income Tax Considerations to Non-U.S. Holders”, insofar as such statements summarize legal matters, agreements, documents or proceedings discussed therein, are
accurate and fair summaries of such legal matters, agreements, documents or proceedings. 
 (p) Absence of
Manipulation. None of the Company, any Closing Date Guarantor or any Merger Date Guarantor has taken, directly or indirectly, any action that is designed to or that has constituted or that would reasonably be expected to cause or result in the
stabilization or manipulation of the price of any security of the Company to facilitate the sale or resale of the Offered Securities (it being understood that the representations and warranties of the Company and the Closing Date Guarantors in this
paragraph (p) with respect to the Merger Date Guarantors are made to the knowledge of the Company and each Closing Date Guarantor). 
 (q) Internal Controls and Compliance with the Sarbanes-Oxley Act. Except as set forth in the General Disclosure Package, (i) Express Scripts, its subsidiaries and its Board of Directors and
(ii) Medco, its subsidiaries and its Board of Directors (the “Medco Board”) are in compliance in all material respects with Sarbanes-Oxley. Express Scripts and Medco each maintain a system

  
 7 

 
of internal controls, including, but not limited to, disclosure controls and procedures, internal controls over accounting matters and financial reporting, an internal audit function and legal
and regulatory compliance controls (collectively, “Internal Controls”) that comply with the Securities Laws and are sufficient to provide reasonable assurances that (i) transactions are executed in accordance with
management’s general or specific authorizations, (ii) transactions are recorded as necessary to permit preparation of financial statements in conformity with U.S. Generally Accepted Accounting Principles and to maintain accountability for
assets, (iii) access to assets is permitted only in accordance with management’s general or specific authorization and (iv) the recorded accountability for assets is compared with the existing assets at reasonable intervals and
appropriate action is taken with respect to any differences. Express Scripts’ and Medco’s Internal Control over financial reporting is effective, and the Company is not aware of any material weakness in Express Scripts’ or
Medco’s Internal Control over financial reporting. Except as disclosed in the Disclosure Package and the Final Offering Circular, since December 31, 2010, there has been no change in Express Scripts’ Internal Control over financial
reporting and, since December 25, 2010, there has been no change in Medco’s Internal Control over financial reporting that, in each case, has materially affected, or is reasonably likely to materially affect, Express Scripts’ or
Medco’s, as applicable, Internal Control over financial reporting. Express Scripts and Medco maintain “disclosure controls and procedures” (as such term is defined in Rule 13a–15(e) under the Exchange Act) that comply with the
requirements of the Exchange Act; such disclosure controls and procedures have been designed to ensure that material information relating to Express Scripts and its subsidiaries or Medco and its subsidiaries is made known to the applicable parent
entity’s principal executive officer and principal financial officer by others within those entities; and such disclosure controls and procedures are effective. It is understood that the representations and warranties of the Company and the
Closing Date Guarantors in this paragraph (q) with respect to Medco, its subsidiaries and the Medco Board are made to the knowledge of the Company and each Closing Date Guarantor. 

(r) Litigation. Except as disclosed in the General Disclosure Package, there are no pending actions, suits or
proceedings (including any inquiries or investigations by or before any court or governmental agency or body, domestic or foreign), involving Express Scripts or any of its subsidiaries or Medco or any of its subsidiaries or any of their respective
properties that, if determined adversely to Express Scripts or any of its subsidiaries or Medco or any of its subsidiaries, as applicable, would individually or in the aggregate have a Material Adverse Effect, or would materially and adversely
affect the ability of the Company or any Guarantor to perform its obligations, as applicable, under the Indenture (including each Guarantee set forth therein), this Agreement, the Joinder Agreements, the Registration Rights Agreements or the
Registration Rights Joinders; and no such actions, suits or proceedings (including any inquiries or investigations by any court or governmental agency or body, domestic or foreign) are, to the Company’s knowledge, threatened. It is understood
that the representations and warranties of the Company and the Closing Date Guarantors in this paragraph (r) with respect to Medco, any of its subsidiaries or any of their respective properties are made to the knowledge of the Company and each
Closing Date Guarantor. 
 (s) Medicare; Medicaid. Except as disclosed in the General Disclosure Package
and the Final Offering Circular, none of the Company, any Closing Date Guarantor or any Merger Date Guarantor has received written notice of any, and to the knowledge of the Company or of Express Scripts there are no, material Medicare, Medicaid, or
any other managed care recoupment or recoupments of any third-party payor being sought, threatened, requested or claimed against the Company, any Closing Date Guarantor or any Merger Date Guarantor (it being understood that the representations and
warranties of the Company and the Closing Date Guarantors in this paragraph (s) with respect to the Merger Date Guarantors are made to the knowledge of the Company and each Closing Date Guarantor). 

(t) Financial Statements. The financial statements included or incorporated by reference in the Final Offering
Circular and the General Disclosure Package together with the related schedules and notes present fairly in all material respects the financial position of Express Scripts and its consolidated subsidiaries and Medco and its consolidated
subsidiaries, in each case, as of 

  
 8 

 
the dates shown and their results of operations and cash flows for the periods shown, and such financial statements have been prepared in conformity with the generally accepted accounting
principles in the United States applied on a consistent basis with respect to Express Scripts and Medco, respectively, and the schedules included or incorporated by reference in the General Disclosure Package present fairly the information required
to be stated therein, and the assumptions used in preparing the pro forma financial information included in the Final Offering Circular and the General Disclosure Package provide a reasonable basis for presenting the significant effects directly
attributable to the transactions or events described therein, the related pro forma adjustments give appropriate effect to those assumptions, and the pro forma columns therein reflect the proper application of those adjustments to the corresponding
historical financial statement amounts. It is understood that the representations and warranties of the Company and the Closing Date Guarantors in this paragraph (t) with respect to the historical financial statements of Medco are made to the
knowledge of the Company and each Closing Date Guarantor. 
 (u) Capitalization. The stockholder’s
equity, cash and cash equivalents and long-term indebtedness of Express Scripts as of September 30, 2011 was as set forth in the General Disclosure Package in the column entitled “Actual” under the caption “Capitalization”;
and there has not been (i) any subsequent issuance of capital stock of Express Scripts, except for subsequent issuances, if any, pursuant to any outstanding securities, benefit or compensation plans disclosed in the General Disclosure Package
or (ii) any subsequent increase, if any, in the outstanding principal amount of long-term indebtedness, except as otherwise disclosed in the General Disclosure Package or under instruments outstanding at September 30, 2011. The long-term
indebtedness of Medco as of September 30, 2011 to be assumed in the Mergers was as set forth in the General Disclosure Package in the column entitled “Pro Forma for the Mergers and the Related Financing Transactions” under the caption
“Capitalization” (it being understood that the representations and warranties of the Company and the Closing Date Guarantors in this paragraph (u) with respect to the long-term indebtedness of Medco are made to the knowledge of the
Company and each Closing Date Guarantor). 
 (v) No Material Adverse Change in Business. Except as
disclosed in the General Disclosure Package, since the end of the period covered by the latest financial statements included or incorporated by reference in the General Disclosure Package (i) there has been no change, nor any development or
event involving a prospective change, in the condition (financial or otherwise), results of operations, business or properties of either (x) Express Scripts and its subsidiaries, taken as a whole, or (y) to the knowledge of the Company and
the Closing Date Guarantors, the Company and its subsidiaries, taken as a whole after giving pro forma effect to the Mergers, that is material and adverse, (ii) except as disclosed in or contemplated by the General Disclosure Package, there has
been no dividend or distribution of any kind declared, paid or made by Express Scripts or, to the knowledge of the Company, Medco on any class of its capital stock and (iii) except as disclosed in or contemplated by the General Disclosure
Package, there has been no material adverse change in the capital stock, short-term indebtedness, long-term indebtedness, net current assets or net assets of Express Scripts or any of its subsidiaries or, to the knowledge of the Company, Medco or
any of its subsidiaries. 
 (w) Investment Company Act. Each of the Company and Express Scripts is not
and, after giving effect to the offering and sale of the Offered Securities and the application of the proceeds thereof as described in the General Disclosure Package, will not be an “investment company” as defined in the Investment
Company Act of 1940 (the “Investment Company Act”). 
 (x) Anti-Bribery Laws. None of
Express Scripts or any of its subsidiaries or, to the knowledge of the Company and each Closing Date Guarantor, Medco or any of its subsidiaries or any director, officer, agent, employee or affiliate of Express Scripts or any of its subsidiaries or,
to the knowledge of the Company and each Closing Date Guarantor, Medco or any of its subsidiaries is aware of or has taken any action, directly or indirectly, that would result in a violation by such persons of the Foreign Corrupt Practices Act of
1977, as amended, and the rules and regulations thereunder (the “FCPA”), including making use of the mails or any means or instrumentality of interstate commerce corruptly in furtherance of an offer, payment, promise to pay or
authorization 

  
 9 

 
of the payment of any money, or other property, gift, promise to give, or authorization of the giving of anything of value to any “foreign official” (as such term is defined in the
FCPA) or any foreign political party or official thereof or any candidate for foreign political office, in contravention of the FCPA; and Express Scripts and its subsidiaries and affiliates and, to the knowledge of the Company and each Closing Date
Guarantor, Medco and its subsidiaries and affiliates, have conducted their businesses in compliance with the FCPA and have instituted and maintain policies and procedures designed to ensure, and which are reasonably expected to continue to ensure,
continued compliance therewith. 
 (y) Money Laundering Laws. The operations of Express Scripts and its
subsidiaries and, to the knowledge of the Company and each Closing Date Guarantor, Medco and its subsidiaries are and have been conducted at all times in compliance with applicable financial record keeping and reporting requirements relating to
money laundering applicable to Express Scripts and its subsidiaries and Medco and its subsidiaries, as applicable, and, so far as the Company is aware, any related or similar statutes, rules, regulations or guidelines, issued, administered or
enforced by any governmental agency (collectively, the “Money Laundering Laws”), and no action, suit or proceeding by or before any court or governmental agency, authority or body or any arbitrator involving Express Scripts or any
of its subsidiaries or, to the knowledge of the Company and each Closing Date Guarantor, Medco or any of its subsidiaries with respect to the Money Laundering Laws is pending or, to the knowledge of the Company, threatened. 

(z) OFAC. None of Express Scripts, any of its subsidiaries or any director, officer, agent, employee or affiliate
of Express Scripts or any of its subsidiaries or, to the knowledge of the Company and each Closing Date Guarantor, Medco, any of its subsidiaries or any director, officer, agent, employee or affiliate of Medco or any of its subsidiaries is currently
subject to any sanctions administered or enforced by the Office of Foreign Assets Control of the U.S. Treasury Department (“OFAC”); and the Company will not directly or indirectly use the proceeds of the offering, or lend,
contribute or otherwise make available such proceeds to any subsidiary, Express Scripts, any joint venture partner or any other person or entity, for the purpose of financing the activities of any person currently subject to any U.S. sanctions
administered by OFAC or in any other manner that will result in a violation of any U.S. sanctions administered by OFAC. 
 (aa) Class of Securities Not Listed. No securities of the same class (within the meaning of Rule 144A(d)(3)) as the Offered Securities are listed on any national securities exchange registered
under Section 6 of the Exchange Act or quoted in a U.S. automated inter-dealer quotation system. 
 (bb)
No Registration. Assuming compliance by the Initial Purchasers with their representations and warranties in Section 4 of this Agreement, the offer and sale of the Offered Securities in the manner contemplated by this Agreement will be
exempt from the registration requirements of the Securities Act by reason of Section 4(2) thereof and Regulation S; and it is not necessary to qualify an indenture in respect of the Offered Securities under the Trust Indenture Act. 

(cc) No Issuer Free Writing Communications. None of the Company, any Closing Date Guarantor or any Merger Date
Guarantor has made, and, without the prior consent of the Representatives, none of the Company, any Closing Date Guarantor or any Merger Date Guarantor will make, any offer relating to the Offered Securities that would constitute an Issuer Free
Writing Communication. 
 (dd) No General Solicitation; No Directed Selling Efforts. None of the Company,
any Closing Date Guarantor, any Merger Date Guarantor, any of their respective affiliates or any person acting on its or their behalf (other than the Initial Purchasers, as to whom no representation is made) (i) has, within the six-month period
prior to the date hereof, offered or sold in the United States or to any U.S. person (as such terms are defined in Regulation S) the Offered Securities or any security of the same class or series as the Offered Securities (other than the 2.750%
Senior Notes due 2014, the 3.500% Senior Notes due 2016, the 4.750% Senior Notes due 2021 and the 

  
 10 

 
6.125% Senior Notes due 2041, in each case, issued by the Company on November 21, 2011) or (ii) has offered or will offer or sell the Offered Securities (A) in the United States by
means of any form of general solicitation or general advertising within the meaning of Rule 502(c) or (B) with respect to any such securities sold in reliance on Rule 903 of Regulation S, by means of any directed selling efforts within the
meaning of Rule 902(c) of Regulation S. The Company, each Closing Date Guarantor, each Merger Date Guarantor, their respective affiliates and any person acting on its or their behalf (other than the Initial Purchasers, as to whom no representation
is made) have complied and will comply with the offering restrictions requirement of Regulation S. None of the Company, any Closing Date Guarantor or any Merger Date Guarantor will enter into any contractual arrangement with respect to the
distribution of the Offered Securities except for this Agreement. It is understood that the representations and warranties of the Company and the Closing Date Guarantors in this paragraph (dd) with respect to the Merger Date Guarantors are made to
the knowledge of the Company and each Closing Date Guarantor. 
 3. Purchase, Sale and Delivery of Offered Securities. On
the basis of the representations, warranties and agreements herein contained and subject to the terms and conditions set forth herein, the Company agrees to sell to the Initial Purchasers, and each of the Initial Purchasers agrees, severally and not
jointly, to purchase from the Company, at a purchase price of (i) 99.108% of the principal amount thereof of the 2015 Notes, plus accrued interest from February 9, 2012 to the Closing Date, the respective principal amounts of the 2015
Notes set forth opposite the names of the Initial Purchasers in Schedule A hereto, (ii) 98.425% of the principal amount thereof of the 2017 Notes, plus accrued interest from February 9, 2012 to the Closing Date, the respective
principal amounts of the 2017 Notes set forth opposite the names of the Initial Purchasers in Schedule A hereto and (iii) 97.197% of the principal amount thereof of the 2022 Notes, plus accrued interest from February 9, 2012 to the
Closing Date, the respective principal amounts of the 2022 Notes set forth opposite the names of the Initial Purchasers in Schedule A hereto. 
 The Company will deliver against payment of the respective purchase prices the Offered Securities to be purchased by each Initial Purchaser hereunder and to be offered and sold by the Initial Purchasers
in reliance on Regulation S (the “Regulation S Securities”) in the form of one or more permanent global securities in registered form without interest coupons (the “Offered Regulation S Global Securities”) which
will be deposited with the Trustee as custodian for The Depository Trust Company (“DTC”) for the respective accounts of the DTC participants for Morgan Guaranty Trust Company of New York, Brussels office, as operator of the
Euroclear System (“Euroclear”), and Clearstream Banking, société anonyme (“Clearstream, Luxembourg”), and as registered in the name of Cede & Co., as nominee for DTC. The Company will deliver
against payment of the respective purchase prices the Offered Securities to be purchased by each Initial Purchaser hereunder and to be offered and sold by each Initial Purchaser in reliance on Rule 144A (the “144A Securities”) in
the form of one or more permanent global securities in definitive form without interest coupons (the “Restricted Global Securities”) deposited with the Trustee as custodian for DTC and registered in the name of Cede & Co.,
as nominee for DTC. The Regulation S Global Securities and the Restricted Global Securities of each series of Offered Securities shall be assigned separate CUSIP numbers. The Restricted Global Securities shall include the legend regarding
restrictions on transfer set forth under “Transfer Restrictions” in the Final Offering Circular. Until the termination of the distribution compliance period (as defined in Regulation S) with respect to the offering of the Offered
Securities, interests in the Regulation S Global Securities may only be held by the DTC participants for Euroclear and Clearstream, Luxembourg. Interests in any permanent global Securities will be held only in book-entry form through Euroclear,
Clearstream, Luxembourg or DTC, as the case may be, except in the limited circumstances described in the Final Offering Circular. 
 Payment for the Offered Securities shall be made by the Initial Purchasers in Federal (same day) funds by wire transfer to an account at a bank acceptable to the Representatives drawn to the order of the
Company at the office of Cravath, Swaine & Moore LLP, at 10:00 A.M., New York time, on February 9, 2012, or at such other time not later than seven full business days thereafter as the Representatives and the Company determine,
such time being herein referred to as the “Closing Date”, against delivery to the Trustee as custodian for DTC of (i) the Regulation S Global Securities representing all of the Regulation S Securities for the respective
accounts of the DTC participants for Euroclear and Clearstream, Luxembourg and (ii) the Restricted Global Securities representing all of the offered 144A Securities. The Regulation S Global Securities and the Restricted Global Securities will
be made available for checking at the above office of Cravath, Swaine & Moore LLP at least 24 hours prior to the Closing Date. 

  
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 4. Representations by Initial Purchasers; Resale by Initial Purchasers. (a) Each
Initial Purchaser severally represents and warrants to the Company and the Guarantors that it is an “accredited investor” within the meaning of Regulation D under the Securities Act. 

(b) Each Initial Purchaser severally acknowledges that the Offered Securities and the Guarantees have not been registered
under the Securities Act and may not be offered or sold within the United States or to, or for the account or benefit of, U.S. persons except in accordance with Regulation S or pursuant to an exemption from the registration requirements of the
Securities Act. Each Initial Purchaser severally represents and agrees that it has offered and sold the Offered Securities and the Guarantees, and will offer and sell the Offered Securities and Guarantees (i) as part of its distribution at any
time and (ii) otherwise until 40 days after the later of the commencement of the offering and the Closing Date, only in accordance with Rule 903 or Rule 144A. Accordingly, neither such Initial Purchaser nor its affiliates, nor any persons
acting on its or their behalf, have engaged or will engage in any directed selling efforts with respect to the Offered Securities, and such Initial Purchaser, its affiliates and all persons acting on its or their behalf have complied with and will
comply with the offering restrictions requirement of Regulation S and Rule 144A. Each Initial Purchaser severally agrees that, at or prior to confirmation of sale of the Offered Securities, other than a sale pursuant to Rule 144A, such Initial
Purchaser will have sent to each distributor, dealer or person receiving a selling concession, fee or other remuneration that purchases the Offered Securities from it during the restricted period a confirmation or notice to substantially the
following effect: 
 “The Securities covered hereby have not been registered under the U.S. Securities Act of 1933 (the
“Securities Act”) and may not be offered or sold within the United States or to, or for the account or benefit of, U.S. persons (i) as part of their distribution at any time or (ii) otherwise until 40 days after the later of the
date of the commencement of the offering and the closing date, except in either case in accordance with Regulation S (or Rule 144A if available) under the Securities Act. Terms used above have the meaning given to them by Regulation S.”

 Terms used in this subsection (b) have the meanings given to them by Regulation S. 

(c) Each Initial Purchaser severally agrees that it and each of its affiliates will not offer or sell the Offered
Securities in the United States by means of any form of general solicitation or general advertising within the meaning of Rule 502(c), including, but not limited to, (i) any advertisement, article, notice or other communication published in any
newspaper, magazine or similar media or broadcast over television or radio, or (ii) any seminar or meeting whose attendees have been invited by any general solicitation or general advertising. Each Initial Purchaser severally agrees, with
respect to resales made in reliance on Rule 144A of any Offered Securities, to deliver either with the confirmation of such resale or otherwise prior to settlement of such resale a notice to the effect that the resale of such Offered Securities has
been made in reliance upon the exemption from the registration requirements of the Securities Act provided by Rule 144A. 
 (d) In relation to each Member State of the European Economic Area that has implemented the Prospectus Directive (each, a “Relevant Member State”), each Initial Purchaser severally
represents and agrees that with effect from and including the date on which the Prospectus Directive is implemented in that Relevant Member State (the “Relevant Implementation Date”) it has not made and will not make an offer of
Offered Securities to the public in that Relevant Member State prior to the publication of a prospectus in relation to the Offered Securities that has been approved by the competent authority in that Relevant Member State or, where appropriate,
approved in another Relevant Member State and notified to the competent authority in that Relevant Member State, all in accordance with the Prospectus Directive, except that it may, with effect from and including the Relevant Implementation Date,
make an offer of Offered Securities to the public in that Relevant Member State at any time, 

  
 12 

 (i) to legal entities that are authorized or regulated to operate in the
financial markets or, if not so authorized or regulated, whose corporate purpose is solely to invest in securities; 
 (ii) to any legal entity that has two or more of (A) an average of at least 250 or, if the Relevant Member State has implemented the relevant provisions of the 2010 PD Amending Directive, 150
employees during the last financial year; (B) a total balance sheet of more than €43,000,000 and (C) an annual net turnover of more than €50,000,000, as shown in its last annual or consolidated accounts; 

(iii) to fewer than 100 or, if the Relevant Member State has implemented the relevant provisions of the 2010 PD Amending
Directive, 150 natural or legal persons (other than qualified investors as defined in the Prospectus Directive) subject to obtaining the prior consent of the Representatives for any such offer; or 

(iv) in any other circumstances that do not require the publication by the Company of a prospectus pursuant to Article 3
of the Prospectus Directive. 
 For the purposes of this provision, the expression an “offer of Offered
Securities to the public” in relation to any Offered Security in any Relevant Member State means the communication in any form and by any means of sufficient information on the terms of the offer and the Offered Securities to be offered so as
to enable an investor to decide to purchase or subscribe for the Offered Securities, as the same expression may be varied in that Member State by any measure implementing the Prospectus Directive in that Member State, and the expression
“Prospectus Directive” means Directive 2003/71/EC (and amendments thereto, including the 2010 PD Amending Directive to the extent implemented in the Relevant Member State) and includes any relevant implementing measure in each Relevant
Member State, and “2010 PD Amending Directive” means Directive 2010/73/EU. 
 (e) Each Initial
Purchaser severally represents, warrants and agrees as follows: 
 (i) it has only communicated or caused to be
communicated and will only communicate or cause to be communicated an invitation or inducement to engage in investment activity (within the meaning of section 21 of the Financial Services and Markets Act of 2000 (the “FSMA”))
received by it in connection with the issue or sale of the Offered Securities to persons who have professional experience in matters relating to investments falling within Article 19(5) of the FSMA Order 2005 or in circumstances in which
Section 21(1) of the FSMA does not apply to the Company or the Guarantors; and 
 (ii) it has complied with,
and will comply with all applicable provisions of FSMA with respect to anything done by it in relation to the Offered Securities in, from or otherwise involving the United Kingdom. 

5. Certain Agreements of the Company. The Company and each of the Closing Date Guarantors and, upon execution and delivery of a
Joinder Agreement, each of the Merger Date Guarantors covenants and agrees with the several Initial Purchasers that: 
 (a) Amendments and Supplements to Offering Circulars. Prior to the completion of the sale of the Offered Securities, the Company will promptly advise the Representatives of any proposal to amend or
supplement the Preliminary Offering Circular or Final Offering Circular and will offer the Representatives a reasonable opportunity to comment on such amendment or supplement. If, at any time prior to the completion of the resale of the Offered
Securities by the Initial Purchasers, any event or development occurs as a result of which a part of the General Disclosure Package, any Supplemental Marketing Material, the Preliminary Offering Circular or the Final Offering Circular, if
republished immediately following such event or development, would include an untrue statement of a material fact or would omit to state any material fact necessary in order to make the statements therein, in the light of the circumstances under
which they were made, not misleading, or if it is necessary at any time to amend or supplement the 

  
 13 

 
General Disclosure Package, any Supplemental Marketing Material, the Preliminary Offering Circular or the Final Offering Circular to comply with any applicable law, the Company will promptly
notify the Representatives of such event or development and will promptly prepare and furnish, at its own expense, to the Initial Purchasers and the dealers and any other dealers upon request of the Representatives, an amendment or supplement which
will correct such statement or omission or effect such compliance. Neither the Representatives’ consent to, nor the Initial Purchasers’ delivery of, any such amendment or supplement shall constitute a waiver of any of the conditions set
forth in Section 7 hereof. 
 (b) Furnishing of Offering Circulars. The Company will furnish to the
Representatives copies of the Preliminary Offering Circular, any other document comprising a part of the General Disclosure Package, the Final Offering Circular, all amendments and supplements to such documents and each item of Supplemental
Marketing Material, in each case as soon as available and in such quantities as the Representatives reasonably request. 
 (c) Blue Sky Qualifications. The Company will arrange for the qualification of the Offered Securities for sale and the determination of their eligibility for investment under the laws of such
jurisdictions as the Representatives designate and will continue such qualifications in effect so long as required for the resale of the Offered Securities by the Initial Purchasers; provided that in no event shall the Company be obligated to
qualify to do business in any jurisdiction where it is not now so qualified or to take any action that would subject it to service of process in suits, other than those arising out of the offering or sale of the Offered Securities, in any
jurisdiction where it is not now so subject. 
 (d) [Reserved.] 

(e) Transfer Restrictions. During the period of one year after the Closing Date, the Company will, upon request,
furnish to the Representatives, each of the other Initial Purchasers and any holder of Offered Securities a copy of the restrictions on transfer applicable to the Offered Securities. 

(f) No Resales by Affiliates. During the period of one year after the Closing Date, the Company will not and will
use its commercially reasonable efforts to not permit any of its affiliates (as defined in Rule 144) to, resell any of the Offered Securities which constitute “restricted securities” under Rule 144A that have been reacquired by them.

 (g) Investment Company. During the period of one year after the Closing Date, the Company will not be
or become an open-ended investment company, unit investment trust or face-amount certificate company that is or is required to be registered under Section 8 of the Investment Company Act. 

(h) Payment of Expenses. The Company will pay all expenses incidental to the performance of the obligations of the
Company and the Guarantors under this Agreement and the Registration Rights Agreements, including but not limited to any expenses (including reasonable fees and disbursements of counsel to the Initial Purchasers) incurred in connection with
qualification of the Offered Securities for sale under the laws of such jurisdictions as the Representatives designate and the preparation and printing of circulars relating thereto, any fees charged by investment rating agencies for the rating of
the Offered Securities or the Exchange Securities, costs and expenses relating to investor presentations or any “road show” in connection with the offering and sale of the Offered Securities including, without limitation, any travel
expenses of the Company’s and the Guarantors’ officers and employees and any other expenses of the Company and the Guarantors, including the chartering of airplanes, fees and expenses in connection with the issuance, offer or sale of the
Offered Securities and the Exchange Securities, and expenses incurred in preparing, printing and distributing this Agreement, the Offered Securities, the Exchange Securities, the Indenture, the Registration Rights Agreements, any Supplemental
Marketing Materials, the General Disclosure Package and the Final Offering Circular (including any amendments and supplements thereto) to the Initial Purchasers. 

  
 14 

 (i) Use of Proceeds. The Company will use the net proceeds received
in connection with this offering in the manner described in the “Use of Proceeds” section of the General Disclosure Package and, except as disclosed in the General Disclosure Package, the Company does not intend to use any of the proceeds
from the sale of the Offered Securities hereunder to repay any outstanding debt owed to any affiliate of any Initial Purchaser. 
 (j) Absence of Manipulation. Neither the Company nor any Closing Date Guarantor will take, directly or indirectly, any action designed to or that would constitute or that might reasonably be
expected to cause or result in, stabilization or manipulation of the price of any securities of the Company to facilitate the sale or resale of the Offered Securities. 

(k) Restriction on Sale of Securities. Neither the Company nor any Closing Date Guarantor will offer, sell,
contract to sell, pledge or otherwise dispose of, directly or indirectly, or file with the Commission (except pursuant to the Registration Rights Agreements) a registration statement under the Securities Act relating to United States
dollar-denominated debt securities issued or guaranteed by the Company or any Closing Date Guarantor and having a maturity of more than one year from the date of issue, or publicly disclose the intention to make any such offer, sale, pledge,
disposition or filing, without the prior written consent of the Representatives for a period beginning on the date hereof and ending on the Closing Date. None of the Company, Express Scripts or their respective subsidiaries will at any time,
directly or indirectly, take any action with respect to any securities under circumstances where the offer, sale, pledge, contract or disposition thereof would cause the exemption afforded by Section 4(2) of the Securities Act or the safe
harbor of Regulation S thereunder to cease to be applicable to the offer and sale of the Offered Securities. 

(l) Joinder Agreement, Supplemental Indenture and Registration Rights Joinder. On the Merger Date, the Company
shall cause Medco to execute and deliver a Joinder Agreement, a Supplemental Indenture and a Registration Rights Joinder in respect of each Registration Rights Agreement and shall deliver such executed counterparts to the Initial Purchasers. On the
date that each other Merger Date Guarantor is required to guarantee the Offered Securities pursuant to the terms of the Indenture, the Company shall cause each such other Merger Date Guarantor to execute and deliver a Joinder Agreement, a
Supplemental Indenture and a Registration Rights Joinder in respect of each Registration Rights Agreement and shall deliver such executed counterparts to the Initial Purchasers. 

6. Free Writing Communications. (a) Issuer Free Writing Communications. The Company and each Closing Date Guarantor
represents and agrees that, unless it obtains the prior consent of the Representatives, and each Initial Purchaser represents and agrees that, unless it obtains the prior consent of the Company and the Representatives, it has not made and will not
make any offer relating to the Offered Securities that would constitute an Issuer Free Writing Communication. 

(b) Term Sheets. The Company consents to the use by any Initial Purchaser of a Free Writing Communication that
(i) contains only (x) information describing the preliminary terms of the Offered Securities or their offering or (y) information that describes the final terms of the Offered Securities or their offering and that is included in the
pricing term sheet substantially in the form of Annex A hereto, or (ii) does not contain any material information about the Company, the Guarantors or any of their securities that was provided by or on behalf of the Company or any Guarantor.

 7. Conditions of the Obligations of the Initial Purchasers. The obligations of the Initial Purchasers to purchase and
pay for the Offered Securities on the Closing Date will be subject to the accuracy of the representations and warranties of the Company and the Closing Date Guarantors herein (as though made on the Closing Date), to the accuracy of the statements of
the individuals made pursuant to the provisions hereof, to the performance by the Company and each Closing Date Guarantor of its obligations hereunder and to the following additional conditions precedent: 

(a) Express Scripts Accountants’ Comfort Letter. The Initial Purchasers shall have received letters, dated,
respectively, the date hereof on the General Disclosure Package and the Closing Date on the Final Offering Circular, of PricewaterhouseCoopers LLP, confirming that they are a registered public accounting firm and independent public accountants with
respect to the Express Scripts, within the meaning of the Securities Laws and substantially in the form of Schedule D-1 hereto (except that, in any letter dated the Closing Date, the specified date referred to in Schedule D-1 hereto shall be a date
no more than three days prior to the Closing Date). 

  
 15 

 (b) Medco Accountants’ Comfort Letter. The Initial Purchasers
shall have received letters, dated, respectively, the date hereof on the General Disclosure Package and the Closing Date on the Final Offering Circular, of PricewaterhouseCoopers LLP, confirming that they are a registered public accounting firm and
independent public accountants with respect to Medco, within the meaning of the Securities Laws and substantially in the form of Schedule D-2 hereto (except that, in any letter dated the Closing Date, the specified date referred to in Schedule D-2
hereto shall be a date no more than four days prior to the Closing Date). 
 (c) No Material Adverse
Change. Subsequent to the execution and delivery of this Agreement, there shall not have occurred (i) any change, or any development or event involving a prospective change, in the condition (financial or otherwise), results of operations,
business or properties of either (x) Express Scripts and its subsidiaries taken as a whole or (y) the Company and its subsidiaries taken as a whole after giving pro forma effect to the Mergers, which, in the judgment of the
Representatives, is material and adverse and makes it impractical or inadvisable to market the Offered Securities; (ii) any downgrading in the rating of any debt securities of the Company, Express Scripts or Medco by any “nationally
recognized statistical rating organization” (as defined under Section 3 of the Exchange Act), or any public announcement that any such organization has under surveillance or review its rating of any debt securities of the Company, Express
Scripts or Medco (other than an announcement with positive implications of a possible upgrading, and no implication of a possible downgrading, of such rating); (iii) any change in U.S. or international financial, political or economic
conditions or currency exchange rates or exchange controls the effect of which is such as to make it, in the judgment of the Representatives, impractical or inadvisable to market or to enforce contracts for the sale of the Offered Securities,
whether in the primary market or in respect of dealings in the secondary market; (iv) any suspension or material limitation of trading in securities generally on the NASDAQ Stock Market, or any setting of minimum or maximum prices for trading
on such exchange; (v) or any suspension of trading of any securities of Express Scripts or Medco on any exchange or in the over-the-counter market; (vi) any banking moratorium declared by any U.S. Federal or New York authorities;
(vii) any major disruption of settlements of securities, payment, or clearance services in the United States or any other country where such securities are listed; or (viii) any attack on, outbreak or escalation of hostilities or act of
terrorism involving the United States, any declaration of war by Congress or any other national or international calamity or emergency if, in the judgment of the Representatives, the effect of any such attack, outbreak, escalation, act, declaration,
calamity or emergency is such as to make it impractical or inadvisable to market the Offered Securities or to enforce contracts for the sale of the Offered Securities. 

(d) Opinion of Counsel for Company and the Closing Date Guarantors. The Initial Purchasers shall have received
opinions and a negative assurance letter, in each case dated the Closing Date, of Skadden, Arps, Slate, Meagher & Flom LLP, counsel for the Company and the Closing Date Guarantors, substantially in the form set forth in Schedules E-1, E-2
and E-3 hereto. 
 (e) Opinion of General Counsel. The Initial Purchasers shall have received an opinion,
dated the Closing Date, of Keith Ebling, General Counsel of Express Scripts substantially in the form set forth in Schedule F hereto. 
 (f) Opinions of Local Counsel for the Closing Date Guarantors. The Initial Purchasers shall have received opinions, dated the Closing Date, of local counsel for the Closing Date Guarantors,
substantially in the form set forth in Schedule G hereto. 

  
 16 

 (g) Opinion of Regulatory Counsel. The Initial Purchasers shall have
received an opinion, dated the Closing Date, of Holland & Knight LLP, special regulatory counsel of Express Scripts, to the effect the statements in the General Disclosure Package and Final Offering Circular (including the documents
incorporated by reference therein) under any headings relating to regulatory disclosure, insofar as they constitute summaries of legal documents, legal proceedings or refer to matters of law or legal conclusions, are accurate in all material
respects. 
 (h) Opinion of Counsel for Initial Purchasers. The Initial Purchasers shall have received
from Cravath, Swaine & Moore LLP, counsel for the Initial Purchasers, such opinion or opinions, dated the Closing Date, with respect to such matters as the Initial Purchasers may require, and the Company shall have furnished to such
counsel such documents as they request for the purpose of enabling them to pass upon such matters. 
 (i)
Officer’s Certificate. The Initial Purchasers shall have received a certificate, dated the Closing Date, of an executive officer of each of the Company and Express Scripts and a principal financial or accounting officer of each of the
Company and Express Scripts in which such officers shall state that: the representations and warranties of the Company and the Closing Date Guarantors in this Agreement are true and correct; the Company and the Closing Date Guarantors have complied
with all agreements and satisfied all conditions on their part to be performed or satisfied hereunder at or prior to the Closing Date; and, subsequent to the date of the most recent financial statements included or incorporated by reference in the
General Disclosure Package, there has been no Material Adverse Effect except as set forth in the General Disclosure Package or as described in such certificate. 
 (j) Indenture and Registration Rights Agreements. The Base Indenture, the Supplemental Indentures to be dated the Closing Date and the Registration Rights Agreements shall have been duly executed
and delivered, and the Initial Purchasers shall have received copies, conformed and executed thereof. 
 The Company will furnish the Initial
Purchasers with such conformed copies of such opinions, certificates, letters and documents as the Initial Purchasers reasonably request. The Representatives may in their sole discretion waive on behalf of the Initial Purchasers compliance with any
conditions to the obligations of the Initial Purchasers hereunder. 
 8. Indemnification and Contribution.
(a) Indemnification of the Initial Purchasers. Each of the Company and each Closing Date Guarantor, as of the date hereof, and each Merger Date Guarantor, upon execution and delivery of a Joinder Agreement, agree and undertake to the
Initial Purchasers that they will, jointly and severally, indemnify and hold harmless each Initial Purchaser, its partners, members, directors, officers, employees, agents, affiliates and each person, if any, who controls such Initial Purchaser
within the meaning of Section 15 of the Securities Act or Section 20 of the Exchange Act (each, an “Indemnified Party”), against any and all losses, claims, damages or liabilities, joint or several, to which such
Indemnified Party may become subject, under the Securities Act, the Exchange Act, other Federal or state statutory law or regulation or otherwise, insofar as such losses, claims, damages or liabilities (or actions in respect thereof) arise out of or
are based upon any untrue statement or alleged untrue statement of any material fact contained in any part of the Preliminary Offering Circular or Final Offering Circular, in each case as amended or supplemented, or any Issuer Free Writing
Communication (including with limitation, any Supplemental Marketing Material) or the General Disclosure Package, or arise out of or are based upon the omission or alleged omission of a material fact required to be stated therein or necessary to
make the statements therein, in the light of the circumstances under which they were made, not misleading, and will reimburse each Indemnified Party for any legal or other expenses reasonably incurred by such Indemnified Party in connection with
investigating or defending against any loss, claim, damage, liability, action, litigation, investigation or proceeding whatsoever (whether or not such Indemnified Party is a party thereto), whether threatened or commenced, and in connection with the
enforcement of this provision with respect to any of the above as such expenses are incurred; provided, however, that the Company and the Guarantors will not be liable in any such case to the extent that any such loss, claim, damage or liability
arises out of or is based upon an untrue statement or alleged untrue statement in or omission or alleged omission from any of such documents in reliance upon and in conformity with written information

  
 17 

 
furnished to the Company by any Initial Purchaser through the Representatives specifically for use therein, it being understood and agreed that the only such information furnished by any Initial
Purchaser consists of the information described as such in subsection (b) below. 
 (b) Indemnification
of the Company. Each Initial Purchaser will severally and not jointly indemnify and hold harmless the Company and each of the Closing Date Guarantors, as of the date hereof, and each Merger Date Guarantor, upon execution and delivery of a
Joinder Agreement, each of their respective directors and each of their respective officers and each person, if any, who controls the Company or any Closing Date Guarantor, as of the date hereof, or any Merger Date Guarantor, upon execution and
delivery of a Joinder Agreement, within the meaning of Section 15 of the Securities Act or Section 20 of the Exchange Act (each, an “Purchaser Indemnified Party”), against any and all losses, claims, damages or liabilities
to which such Purchaser Indemnified Party may become subject, under the Securities Act, the Exchange Act, other Federal or state statutory law or regulation or otherwise, insofar as such losses, claims, damages or liabilities (or actions in respect
thereof) arise out of or are based upon (i) any untrue statement or alleged untrue statement of any material fact contained in any part of the Preliminary Offering Circular or the Final Offering Circular, in each case as amended or
supplemented, or any Issuer Free Writing Communication or the General Disclosure Package, or arise out of or are based upon the omission or alleged omission of a material fact required to be stated therein or necessary to make the statements
therein, in the light of the circumstances under which they were made, not misleading, in each case to the extent, but only to the extent, that such untrue statement or alleged untrue statement or omission or alleged omission was made in reliance
upon and in conformity with written information furnished to the Company by such Initial Purchaser through the Representatives specifically for use therein, and will reimburse any legal or other expenses reasonably incurred by such Purchaser
Indemnified Party in connection with investigating or defending against any such loss, claim, damage, liability, action, litigation, investigation or proceeding whatsoever (whether or not such Purchaser Indemnified Party is a party thereto), whether
threatened or commenced, based upon any such untrue statement or omission, or any such alleged untrue statement or omission as such expenses are incurred, it being understood and agreed that the only such information furnished by any Initial
Purchaser consists of the following information in the Preliminary Offering Circular and the Final Offering Circular furnished on behalf of each Initial Purchaser: under the caption “Plan of Distribution”, the third, twelfth and thirteenth
paragraphs and the second sentence of the eleventh paragraph. 
 (c) Actions against Parties;
Notification. Promptly after receipt by an indemnified party under this Section of notice of the commencement of any action, such indemnified party will, if a claim in respect thereof is to be made against the indemnifying party under subsection
(a) or (b) above, notify the indemnifying party of the commencement thereof; but the failure to notify the indemnifying party shall not relieve it from any liability that it may have under subsection (a) or (b) above except to
the extent that it has been materially prejudiced (through the forfeiture of substantive rights or defenses) by such failure; and provided further that the failure to notify the indemnifying party shall not relieve it from any liability that it may
have to an indemnified party otherwise than under subsection (a) or (b) above. In case any such action is brought against any indemnified party and it notifies the indemnifying party of the commencement thereof, the indemnifying party will
be entitled to participate therein and, to the extent that it may wish, jointly with any other indemnifying party similarly notified, to assume the defense thereof, with counsel satisfactory to such indemnified party (who shall not, except with the
consent of the indemnified party, be counsel to the indemnifying party), and after notice from the indemnifying party to such indemnified party of its election so to assume the defense thereof, the indemnifying party will not be liable to such
indemnified party under this Section for any legal or other expenses subsequently incurred by such indemnified party in connection with the defense thereof other than reasonable costs of investigation. No indemnifying party shall, without the prior
written consent of the indemnified party, effect any settlement of any pending or threatened action in respect of which any indemnified party is or could have been a party and indemnity could have been sought hereunder by such indemnified party
unless such settlement (i) includes an unconditional release of such indemnified party from all liability on any claims that are the subject matter of such action and (ii) does not include a statement as to, or an admission of, fault,
culpability or a failure to act by or on behalf of an indemnified party. 

  
 18 

 (d) Contribution. If the indemnification provided for in this Section
is unavailable or insufficient to hold harmless an indemnified party under subsection (a) or (b) above, then each indemnifying party shall contribute to the amount paid or payable by such indemnified party as a result of the losses,
claims, damages or liabilities referred to in subsection (a) or (b) above (i) in such proportion as is appropriate to reflect the relative benefits received by the Company and the Guarantors on the one hand and the Initial Purchasers
on the other from the offering of the Offered Securities or (ii) if the allocation provided by clause (i) above is not permitted by applicable law, in such proportion as is appropriate to reflect not only the relative benefits referred to
in clause (i) above but also the relative fault of the Company and the Guarantors on the one hand and the Initial Purchasers on the other in connection with the statements or omissions which resulted in such losses, claims, damages or
liabilities as well as any other relevant equitable considerations. The relative benefits received by the Company and the Guarantors on the one hand and the Initial Purchasers on the other shall be deemed to be in the same proportion as the total
net proceeds from the offering (before deducting expenses) received by the Company and the Guarantors bear to the total discounts and commissions received by the Initial Purchasers. The relative fault shall be determined by reference to, among other
things, whether the untrue or alleged untrue statement of a material fact or the omission or alleged omission to state a material fact relates to information supplied by the Company or any Guarantor or the Initial Purchasers and the parties’
relative intent, knowledge, access to information and opportunity to correct or prevent such untrue statement or omission. The amount paid by an indemnified party as a result of the losses, claims, damages or liabilities referred to in the first
sentence of this subsection (d) shall be deemed to include any legal or other expenses reasonably incurred by such indemnified party in connection with investigating or defending any action or claim which is the subject of this subsection (d).
Notwithstanding the provisions of this subsection (d), no Initial Purchaser shall be required to contribute any amount in excess of the amount by which the total price at which the Securities purchased by it were resold exceeds the amount of any
damages which such Initial Purchaser has otherwise been required to pay by reason of such untrue or alleged untrue statement or omission or alleged omission. No person guilty of fraudulent misrepresentation (within the meaning of Section 11(f)
of the Securities Act) shall be entitled to contribution from any person who was not guilty of such fraudulent misrepresentation. The Initial Purchasers’ obligations in this subsection (d) to contribute are several in proportion to their
respective purchase obligations and not joint. The Company, the Guarantors and the Initial Purchasers agree that it would not be just and equitable if contribution pursuant to this Section 8(d) were determined by pro rata allocation (even if
the Initial Purchasers were treated as one entity for such purpose) or by any other method of allocation which does not take account of the equitable considerations referred to in this Section 8(d). 

9. Default of Initial Purchasers. If any Initial Purchaser or Initial Purchasers default in their obligations to purchase Offered
Securities hereunder on the Closing Date and the aggregate principal amount of Offered Securities that such defaulting Initial Purchaser or Initial Purchasers agreed but failed to purchase does not exceed 10% of the total principal amount of Offered
Securities that the Initial Purchasers are obligated to purchase on the Closing Date, the Representatives may make arrangements satisfactory to the Company for the purchase of such Offered Securities by other persons, including any of the Initial
Purchasers, but if no such arrangements are made by the Closing Date, the non-defaulting Initial Purchasers shall be obligated severally, in proportion to their respective commitments hereunder, to purchase the Offered Securities that such
defaulting Initial Purchasers agreed but failed to purchase on the Closing Date. If any Initial Purchaser or Initial Purchasers so default and the aggregate principal amount of Offered Securities with respect to which such default or defaults occur
exceeds 10% of the total principal amount of Offered Securities that the Initial Purchasers are obligated to purchase on the Closing Date and arrangements satisfactory to the Representatives and the Company for the purchase of the Offered Securities
by other persons are not made within 36 hours after such default, this Agreement will terminate without liability on the part of any non-defaulting Initial Purchaser or the Company, except as provided in Section 10. As used in this Agreement,
the term “Initial Purchaser” includes any person substituted for a Initial Purchaser under this Section. Nothing herein will relieve a defaulting Initial Purchaser from liability for its default. 

  
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 10. Survival of Certain Representations and Obligations. The respective indemnities,
agreements, representations, warranties and other statements of the Company, the Closing Date Guarantors, the Merger Date Guarantors and their respective officers and of the Initial Purchasers set forth in or made pursuant to this Agreement will
remain in full force and effect, regardless of any investigation, or statement as to the results thereof, made by or on behalf of any Initial Purchaser, the Company, the Closing Date Guarantors, the Merger Date Guarantors or any of their respective
representatives, officers or directors or any controlling person, and will survive delivery of and payment for the Offered Securities. If the purchase of the Offered Securities by the Initial Purchasers is not consummated for any reason other than
solely because of the termination of this Agreement pursuant to Section 9 hereof, the Company and the Guarantors will reimburse the Initial Purchasers for all out-of-pocket expenses (including fees and disbursements of counsel) reasonably
incurred by them in connection with the offering of the Offered Securities, and the respective obligations of the Company, each Closing Date Guarantor, each Merger Date Guarantor and the Initial Purchasers pursuant to Section 8 hereof shall
remain in effect. 
 11. Notices. All communications hereunder will be in writing and, if sent to the Initial Purchasers,
will be mailed, delivered or telegraphed and confirmed to Citigroup Global Markets Inc., 388 Greenwich Street, New York, N.Y. 10013, Attention: General Counsel and Credit Suisse Securities (USA) LLC, Eleven Madison Avenue, New York, N.Y. 10010-3629,
Attention: LCD-IBD, or, if sent to the Company, will be mailed, delivered or telegraphed and confirmed to it care of Express Scripts, Inc., One Express Way, St. Louis, MO 63121, Attention: Keith Ebling, General Counsel; provided, however, that
any notice to an Initial Purchaser pursuant to Section 8 will be mailed, delivered or telegraphed and confirmed to such Initial Purchaser. 
 12. Successors. This Agreement will inure to the benefit of and be binding upon the parties hereto and their respective successors and the officers and directors and controlling persons referred to
in Section 8, and no other person will have any right or obligation hereunder. 
 13. Representation of Initial
Purchasers. The Representatives will act for the several Initial Purchasers in connection with this purchase, and any action under this Agreement taken by the Representatives jointly will be binding upon all the Initial Purchasers. 

14. Counterparts. This Agreement may be executed in any number of counterparts, each of which shall be deemed to be an original,
but all such counterparts shall together constitute one and the same Agreement. 
 15. Absence of Fiduciary Relationship.
The Company and each Closing Date Guarantor, as of the date hereof, and each Merger Date Guarantor, upon execution and delivery of a Joinder Agreement, acknowledge and agree that: 

(a) No Other Relationship. The Representatives have been retained solely to act as initial purchasers in connection
with the initial purchase, offering and resale of the Offered Securities and that no fiduciary, advisory or agency relationship between the Company and the Guarantors on the one hand and the Representatives on the other hand has been created in
respect of any of the transactions contemplated by this Agreement or the Preliminary Offering Circular or the Final Offering Circular, irrespective of whether the Representatives have advised or are advising the Company and the Guarantors on other
matters; 
 (b) Arms’ Length Negotiations. The prices of the Offered Securities set forth in this
Agreement were established by the Company following discussions and arms-length negotiations with the Representatives and the Company is capable of evaluating and understanding and understands and accepts the terms, risks and conditions of the
transactions contemplated by this Agreement; 
 (c) Absence of Obligation to Disclose. The Company and the
Guarantors have been advised that the Representatives and their affiliates are engaged in a broad range of transactions 

  
 20 

 
which may involve interests that differ from those of the Company and the Guarantors and that the Representatives have no obligation to disclose such interests and transactions to the Company and
the Guarantors by virtue of any fiduciary, advisory or agency relationship; and 
 (d) Waiver. The Company
and the Guarantors waive, to the fullest extent permitted by law, any claims they may have against the Representatives for breach of fiduciary duty or alleged breach of fiduciary duty and agree that the Representatives shall have no liability
(whether direct or indirect) to the Company or any Guarantor in respect of such a fiduciary duty claim or to any person asserting a fiduciary duty claim on behalf of or in right of the Company or any Guarantor, including stockholders, employees or
creditors of the Company. 
 16. Applicable Law. This Agreement
shall be governed by, and construed in accordance with, the laws of the State of New York without regard to principles of conflicts of laws. 
 The Company and each Guarantor hereby submit to the non-exclusive jurisdiction of the Federal and state courts in the Borough of Manhattan in The City of New York in any suit or proceeding arising out of
or relating to this Agreement or the transactions contemplated hereby. The Company and each Guarantor irrevocably and unconditionally waive any objection to the laying of venue of any suit or proceeding arising out of or relating to this Agreement
or the Joinder Agreements or the transactions contemplated hereby in Federal and state courts in the Borough of Manhattan in The City of New York and irrevocably and unconditionally waive and agree not to plead or claim in any such court that any
such suit or proceeding in any such court has been brought in an inconvenient forum. 

  
 21 

 If the foregoing is in accordance with the Representatives’ understanding of our
agreement, kindly sign and return to the Company one of the counterparts hereof, whereupon it will become a binding agreement between the Company and each Guarantor and the several Initial Purchasers in accordance with its terms. 

  
 22 

					
	Very truly yours,
	
	ARISTOTLE HOLDING, INC.
		
	By:	 	 /s/ George Paz

		 	Name:	 	George Paz
		 	Title:	 	 Chairman, Chief Executive Officer
 and President

	
	EXPRESS SCRIPTS, INC.
		
	By:	 	 /s/ George Paz

		 	Name:	 	George Paz
		 	Title:	 	 Chairman, Chief Executive Officer
 and President

	
	AIRPORT HOLDINGS, LLC
	ESI REALTY, LLC
	By: Express Scripts, Inc., as sole Member
		
	By:	 	 /s/ George Paz

		 	Name:	 	George Paz
		 	Title:	 	 Chairman, Chief Executive Officer
 and President

 [Purchase Agreement] 

  
 23 

					
	 BYFIELD DRUG, INC.

	 CARE CONTINUUM, INC.

	 CFI OF NEW JERSEY, INC.

	 CHESAPEAKE INFUSION, INC.

	 CONNECTYOURCARE COMPANY LLC

	 CONNECTYOURCARE, LLC

	 CURASCRIPT PBM SERVICES INC.

	 DIVERSIFIED PHARMACEUTICAL SERVICES, INC.

	 ESI ACQUISITION, INC.

	 ESI CLAIMS, INC.

	 ESI ENTERPRISES, LLC

	 ESI MAIL ORDER PROCESSING, INC.

	 EXPRESS SCRIPTS CANADA HOLDING CO.

	 EXPRESS SCRIPTS PHARMACEUTICAL PROCUREMENT, LLC

	 EXPRESS SCRIPTS SERVICES COMPANY

	 FRECO, INC.

	 FREEDOM SERVICE COMPANY, LLC

	 HEALTHBRIDGE, INC.

	 HEALTHBRIDGE REIMBURSEMENT AND PRODUCT SUPPORT, INC.

	 iBIOLOGIC, INC.

	 IVTX, INC.

	 LYNNFIELD COMPOUNDING CENTER, INC.

	 LYNNFIELD DRUG, INC.

	 MATRIX GPO LLC

	 NATIONAL PRESCRIPTION ADMINISTRATORS, INC.

	 PRIORITY HEALTHCARE CORPORATION

	 PRIORITY HEALTHCARE CORPORATION WEST

	 PRIORITY HEALTHCARE DISTRIBUTION, INC.

	 PRIORITY HEALTHCARE PHARMACY, INC.

	 PRIORITYHEALTHCARE.COM, INC.

	 SINUSPHARMACY, INC.

	 SPECIALTY INFUSION PHARMACY, INC.

	 SPECTRACARE, INC.

	 SPECTRACARE HEALTH CARE VENTURES, INC.

	 SPECTRACARE INFUSION PHARMACY, INC.

	 VALUE HEALTH, INC.

	 YOURPHARMACY.COM, INC.

		
	By:	 	 /s/ Keith J. Ebling

		 	Name:	 	Keith J. Ebling
		 	Title:	 	Vice President

 [Purchase Agreement] 

  
 24 

  

					
	 CURASCRIPT, INC.

	 ESI MAIL PHARMACY SERVICE, INC.

	 EXPRESS SCRIPTS SPECIALTY DISTRIBUTION SERVICES, INC.

	 EXPRESS SCRIPTS UTILIZATION MANAGEMENT CO.

	 MOORESVILLE ON-SITE PHARMACY, LLC

		
	By:	 	 /s/ Patrick McNamee

		 	Name:	 	Patrick McNamee
		 	Title:	 	President

 [Purchase Agreement] 

  
 25 

					
	ESI-GP HOLDINGS, INC.
	ESI RESOURCES, INC.
		
	By:	 	 /s/ Tom Rocheford

		 	Name:	 	Tom Rocheford
		 	Title:	 	President
	
	ESI PARTNERSHIP
	
	By: Express Scripts, Inc., as Partner
		
	By:	 	 /s/ Martin P. Akins

		 	Name:	 	Martin P. Akins
		 	Title:	 	Vice President and Deputy General Counsel
	
	By: ESI-GP Holdings, Inc., as Partner
		
	By:	 	 /s/ Tom Rocheford

		 	Name:	 	Tom Rocheford
		 	Title:	 	President

 [Purchase Agreement] 

  
 26 

					
	SPECTRACARE OF INDIANA
	
	 By: Spectracare, Inc., as Partner

		
	By:	 	 /s/ Keith J. Ebling

		 	Name:	 	Keith J. Ebling
		 	Title:	 	Vice President
	
	By: Care Continuum, Inc., as Partner
		
	By:	 	 /s/ Keith J. Ebling

		 	Name:	 	Keith J. Ebling
		 	Title:	 	Vice President
	
	EXPRESS SCRIPTS MSA, LLC
	EXPRESS SCRIPTS WC, INC.
		
	By:	 	 /s/ Edward Ignaczak

		 	Name:	 	Edward Ignaczak
		 	Title:	 	President
	
	 EXPRESS SCRIPTS SENIOR CARE, INC.

	 EXPRESS SCRIPTS SENIOR CARE HOLDINGS, INC.

		
	By:	 	 /s/ George Paz

		 	Name:	 	George Paz
		 	Title:	 	President
	
	 EXPRESS SCRIPTS CANADA HOLDING, LLC

		
	By:	 	 /s/ Keith J. Ebling

		 	Name:	 	Keith J. Ebling
		 	Title:	 	Vice President

 [Purchase Agreement] 

  
 27 

  

					
	The foregoing Purchase Agreement is hereby confirmed and accepted as of the date first above written.
	
	 Acting on behalf of themselves and as the Representatives of the several Initial Purchasers

	
	 CREDIT SUISSE SECURITIES (USA) LLC

		
	By:	 	 /s/ Michael Muntner

			
		 	Name:	 	Michael Muntner
		 	Title:	 	Managing Director

 [Purchase Agreement] 

  
 28 

  

					
	CITIGROUP GLOBAL MARKETS INC.
		
	By:	 	 /s/ Jack D. McSpadden, Jr.

			
		 	Name:	 	Jack D. McSpadden, Jr.
		 	Title:	 	Managing Director

 [Purchase Agreement] 

  
 29

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