Second Supplemental Indenture



 Exhibit 4.5 
 SECOND SUPPLEMENTAL INDENTURE 
 SECOND SUPPLEMENTAL INDENTURE (this “Second
Supplemental Indenture”), dated as of April 2, 2012, among Medco Health Solutions, Inc., a Delaware corporation (the “Company”), the existing subsidiary guarantors listed as signatories hereto (each, an “Existing
Guarantor” and collectively, the “Existing Guarantors”), the entities listed on Schedule I hereto (each, a “Guarantor” and, collectively, the “Guarantors”), and U.S. Bank Trust National Association, as trustee
under the indenture referred to below (the “Trustee”). 
 W I T N E S S E T H 

WHEREAS, the Company has heretofore executed and delivered to the Trustee an indenture (as amended, the “Indenture”), dated as
of August 12, 2003 providing for the issuance of $500.0 million aggregate principal amount of the Company’s 7.25% Senior Notes due 2013 (the “Notes”); 
 WHEREAS, pursuant to Section 9.01 of the Indenture, the Company is permitted to amend the Indenture to add guarantees with respect to the Notes, as defined in the Indenture and this Second
Supplemental Indenture (the “Guarantees”); and 
 WHEREAS, pursuant to Section 9.01 of the Indenture, the Trustee
is authorized to execute and deliver this Second Supplemental Indenture. 
 NOW THEREFORE, in consideration of the foregoing and
for other good and valuable consideration, the receipt of which is hereby acknowledged, each Guarantor and the Trustee mutually covenant and agree for the equal and ratable benefit of the Holders of the Notes as follows: 

1. Capitalized Terms. Capitalized terms used herein without definition shall have the meanings assigned to them in the Indenture.








 2. Agreement to Guarantee. Each Guarantor hereby agrees as follows: 

(a) To guarantee, jointly and severally with each other Guarantor, each Existing Guarantor and with any other guarantor
hereafter designated as such by the Company, to each Holder of a Note authenticated and delivered by the Trustee and to the Trustee and its successors and assigns, irrespective of the validity and enforceability of the Indenture, the Notes or the
obligations of the Company hereunder or thereunder, that: 
 (i) the principal of, and any premium and interest
on, the Notes will be promptly paid in full when due, whether at maturity, by acceleration, redemption or otherwise, and interest on the overdue principal of and interest on the Notes, if any, if lawful, and all other obligations of the Company to
the Holders or the Trustee hereunder or thereunder will be promptly paid in full or performed, all in accordance with the terms hereof and under the Indenture; and 

(ii) in case of any extension of time of payment or renewal of any Notes or any of such other obligations, that same will
be promptly paid in full when due or performed in accordance with the terms of the extension or renewal, whether at the date scheduled to be paid, by acceleration or otherwise. 
 Failing payment when due of any amount so guaranteed or any performance so guaranteed for whatever reason, each Guarantor shall be obligated to pay the same immediately. Each Guarantor hereby agrees that
this is a guarantee of payment and not a guarantee of collection. 
 (b) The obligations hereunder shall be
unconditional, irrespective of the validity, regularity or enforceability of the Notes or the Indenture, the absence of any action to enforce the same, any waiver or consent by any Holder of the Notes with respect to any provisions hereof or
thereof, the recovery of any judgment against the Company, any action to enforce the same or any other circumstance which might otherwise constitute a legal or equitable discharge or defense of any Guarantor. 

(c) The Guarantors hereby waive diligence, presentment, demand of payment, filing of claims with a court in the event of
insolvency or bankruptcy of the Company, any right to require a proceeding first against the Company, protest, notice and all demands whatsoever. 
 (d) This Guarantee shall not be discharged except by complete performance of the obligations contained in the Notes and the Indenture or release in accordance with the Indenture, and each Guarantor
accepts all obligations of a Guarantor under the Indenture. 







 (e) If any Holder or the Trustee is required by any court or otherwise to
return to the Company, any Guarantor, or any custodian, trustee, liquidator or other similar official acting in relation to either the Company or any Guarantor, any amount paid by any of them to the Trustee or such Holder, this Guarantee, to the
extent theretofore discharged, shall be reinstated in full force and effect. 
 (f) The Guarantors shall not be
entitled to any right of subrogation in relation to the Holders in respect of any obligations guaranteed hereby until payment in full of all obligations guaranteed hereby. 

(g) As between the Guarantors, on the one hand, and the Holders and the Trustee, on the other hand, (x) the maturity
of the obligations guaranteed hereby may be accelerated as provided in Article 6 of the Indenture for the purposes of this Guarantee, notwithstanding any stay, injunction or other prohibition preventing such acceleration in respect of the
obligations guaranteed hereby, and (y) in the event of any declaration of acceleration of such obligations as provided in Article 6 of the Indenture, such obligations (whether or not due and payable) shall forthwith become due and payable by
the Guarantors for the purpose of this Guarantee. 
 (h) After giving effect to any maximum amount and all other
contingent and fixed liabilities that are relevant under any applicable Bankruptcy or fraudulent conveyance laws, this Guarantee shall be limited to the maximum amount permissible such that the obligations of the Guarantors under this Guarantee will
not constitute a fraudulent transfer or conveyance. 
 3. Execution and Delivery. Each Guarantor agrees that the Guarantee shall
remain in full force and effect notwithstanding any failure to endorse such Guarantee. 
 4. [Reserved.] 

5. Releases. Any Guarantor will be, upon action by the Company to the Trustee, released automatically and relieved of any obligations
under its Guarantee. The Trustee will execute any documents reasonably required in order to evidence the release of such Guarantor from its obligations under its Guarantee. 
 6. No Recourse Against Others. No past, present or future director, officer, employee, incorporator, stockholder or agent of any Guarantor, as such, shall have any liability for any obligations of the
Company or any Guarantor under the Notes, the Guarantee, the Indenture or this Second Supplemental Indenture or for any claim based on, in respect of, or by reason of, such obligations or their creation. Each Holder of the Notes by accepting a Note
waives and releases all such liability. The waiver and release are part of the consideration for issuance of the Notes. 







 7. [Reserved.] 
 8. Separability. In case any provision in this Second Supplemental Indenture or in the Guarantee is invalid, illegal or unenforceable, the validity, legality and enforceability of the remaining provisions
will not in any way be affected or impaired thereby. 
 9. Governing Law. This Second Supplemental Indenture and the Guarantee
shall be governed by and construed in accordance with the laws of the State of New York. 
 10. Counterparts. The parties may
sign any number of copies of this Second Supplemental Indenture. Each signed copy shall be an original, but all of them together represent the same agreement. 
 11. Effect of Headings. The Section headings herein are for convenience of reference only, are not to be considered part of this Second Supplemental Indenture and will in no way modify or restrict any of
the terms or provisions hereof. 
 12. The Trustee. The Trustee shall not be responsible in any manner whatsoever for or in
respect of the validity or sufficiency of this Second Supplemental Indenture or for or in respect of any statement or recital herein or in the Guarantee, all of which statements and recitals are made solely by the Guarantors and the Company.








 IN WITNESS WHEREOF, the parties hereto have caused this Second Supplemental Indenture to be
duly executed and attested, all as of the date first above written. 
 Dated: April 2, 2012 

 

							
		 	MEDCO HEALTH SOLUTIONS, INC.
			
		 	By:	 	 /s/ Keith J. Ebling

		 		 	Name:	 	Keith J. Ebling
		 		 	Title:	 	Vice President
	
	Existing Guarantors
		
		 	ACCREDO HEALTH, INCORPORATED
		 	ACCREDO HEALTH GROUP, INC.
		 	MEDCO HEALTH SERVICES, INC.
			
		 	By:	 	 /s/ Keith J. Ebling

		 		 	Name:	 	Keith J. Ebling
		 		 	Title:	 	Vice President
	
	Guarantors
		
		 	EXPRESS SCRIPTS HOLDING COMPANY
			
		 	By:	 	 /s/ Keith J. Ebling

		 	Name:	 	Keith J. Ebling
		 	Title:	 	Executive Vice President, General Counsel, and Secretary
		
		 	EXPRESS SCRIPTS, INC.
			
		 	By:	 	 /s/ Keith J. Ebling

		 	Name:	 	Keith J. Ebling
		 	Title:	 	Vice President
		
		 	AIRPORT HOLDINGS, LLC
		 	ESI REALTY, LLC
			
		 	By:	 	Express Scripts, Inc., as sole Member
			
		 	By:	 	 /s/ Keith J. Ebling

		 	Name:	 	Keith J. Ebling
		 	Title:	 	Vice President


 [Signature Page to 2003 Medco Second Supplemental Indenture] 








					
	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 CANADA HOLDING, LLC
	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 COMPUNDING 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
	
	CURASCRIPT, INC.
	EXPRESS SCRIPTS UTILIZATION MANAGEMENT CO.
	EXPRESS SCRIPTS MSA, LLC
	EXPRESS SCRIPTS SENIOR CARE, INC.
	EXPRESS SCRIPTS SENIOR CARE HOLDINGS, INC.
	EXPRESS SCRIPTS WC, INC.
		
	By:	 	 /s/ Martin P. Akins

		 	Name:	 	Martin P. Akins
		 	Title:	 	Assistant Secretary


 [Signature Page to 2003 Medco Second Supplemental Indenture] 








					
	ESI MAIL PHARMACY SERVICE, INC.
	EXPRESS SCRIPTS SPECIALTY DISTRIBUTION SERVICES, INC.
	MOORESVILLE ON-SITE PHARMACY, LLC
		
	By:	 	 /s/ Martin P. Akins

		 	Name:	 	Martin P. Akins
		 	Title:	 	Secretary
	
	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/ Keith J. Ebling

		 	Name:	 	Keith J. Ebling
		 	Title:	 	Vice President
	
	By: ESI-GP Holdings, Inc., as Partner
		
	By:	 	 /s/ Tom Rocheford

		 	Name:	 	Tom Rocheford
		 	Title:	 	President
	
	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


 [Signature Page to 2003 Medco Second Supplemental Indenture] 








			
	U.S. Bank Trust National Association, as Trustee
		
	By:	 	 /s/ Patrick J. Crowley

		 	Authorized Signatory


 [Signature Page to 2003 Medco Second Supplemental Indenture]