Document:

Eighth Supplemental Indenture

 Exhibit 4.1 
 EIGHTH SUPPLEMENTAL INDENTURE 
 The Eighth Supplemental Indenture (this
“Eighth Supplemental Indenture”), dated as of April 2, 2012, among Express Scripts Holding Company (formerly Aristotle Holding, Inc.), a corporation duly organized and existing under the laws of the State of Delaware (the
“Company”), the Guarantors listed as signatories hereto (each, an “Existing Guarantor” and collectively, the “Existing Guarantors”), Medco Health Solutions, Inc., a Delaware corporation, and its
subsidiaries listed as signatories hereto (each, an “Additional Guarantor,” and, collectively, the “Additional Guarantors”) and Wells Fargo Bank, 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, the Existing Guarantors and the Trustee are parties to the indenture, dated as of November 21, 2011 (the
“Base Indenture”), as supplemented by the First Supplemental Indenture thereto, dated as of November 21, 2011 (the “First Supplemental Indenture”), relating to the Company’s 2.750% Notes due 2014 (the
“2014 Notes”), the Second Supplemental Indenture thereto, dated as of November 21, 2011 (the “Second Supplemental Indenture”), relating to the Company’s 3.500% Notes due 2016 (the “2016
Notes”), the Third Supplemental Indenture thereto, dated as of November 21, 2011 (the “Third Supplemental Indenture”), relating to the Company’s 4.750% Notes due 2021 (the “2021 Notes”), the
Fourth Supplemental Indenture thereto, dated as of November 21, 2011 (the “Fourth Supplemental Indenture”), relating to the Company’s 6.125% Notes due 2041 (the “2041 Notes”), the Fifth Supplemental
Indenture thereto, dated as of February 9, 2012 (the “Fifth Supplemental Indenture”), relating to the Company’s 2.100% Notes due 2015 (the “2015 Notes”), the Sixth Supplemental Indenture thereto, dated as
of February 9, 2012 (the “Sixth Supplemental Indenture”), relating to the Company’s 2.650% Notes due 2017 (the “2017 Notes”) and the Seventh Supplemental Indenture thereto, dated as of February 9,
2012 (together with the First Supplemental Indenture, the Second Supplemental Indenture, the Third Supplemental Indenture, the Fourth Supplemental Indenture, the Fifth Supplemental Indenture and the Sixth Supplemental Indenture, the
“Supplemental Indentures” and the Base Indenture as so supplemented, the “Indenture”), relating to the 3.900% Notes due 2022 (together with the 2014 Notes, the 2016 Notes, the 2021 Notes, the 2041 Notes, the 2015
Notes and the 2017 Notes, the “Notes”); 
 WHEREAS, each Additional Guarantor desires to provide a full and
unconditional guarantee (the “Guarantee”) of the obligations of the Company under the Notes, the Securities (as defined in the Indenture) and the Indenture on the terms and conditions set forth herein; 

WHEREAS, the Company has complied with all conditions precedent provided for in the Indenture and each Supplemental Indenture relating to
this Eighth Supplemental Indenture; and 
 WHEREAS, pursuant to Section 9.1 of the Base Indenture and Section 7.1 of
each Supplemental Indenture, the Company, the Trustee and the Additional Guarantors are authorized to execute and deliver this Eighth Supplemental Indenture. 
 NOW, THEREFORE, for good and valuable consideration, the receipt of which is acknowledged, each Additional Guarantor guarantees the Company’s obligations under the Securities as follows: 

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

 2. Guarantee, Etc. Each Additional Guarantor hereby agrees that from and after the date hereof it shall be a Guarantor
under the Indenture and be bound by its terms thereof applicable to Guarantors and shall be entitled to all of the rights and subject to all of the obligations of a Guarantor thereunder. 

3. Ratification of Indenture; Supplemental Indenture Part of Indenture. The Indenture is in all respects ratified and confirmed,
and all terms, conditions and provisions thereof shall remain in full force and effect. This Eighth Supplemental Indenture shall form a part of the Indenture for all purposes, and every Holder of Securities heretofore or hereafter authenticated and
delivered shall be bound hereby. 
 4. Representations and Warranties. Each Additional Guarantor hereby represents that
(a) it is duly organized, validly existing and in good standing under the laws of the jurisdiction of its organization, (b) it 

 
has full power, authority and legal rights to execute and deliver this Eighth Supplemental Indenture and to perform its obligations hereunder and under the Indenture, (c) the execution,
delivery and performance by it of this Eighth Supplemental Indenture has been duly authorized by all necessary corporate action, and no other proceedings or actions on the part of such Additional Guarantor are necessary therefor and (d) this
Eighth Supplemental Indenture has been duly and validly executed and delivered by such Additional Guarantor and constitutes a legal, valid and binding obligation of such Additional Guarantor, enforceable against such Additional Guarantor in
accordance with its terms (subject to applicable bankruptcy, insolvency, receivership, reorganization, moratorium and other similar laws of general applicability relating to or affecting creditors’ rights and to general equity principles).

 5. No Personal Liability of Directors, Officers, Employees or Stockholders. No director, officer, employee, member or
stockholder of any Additional Guarantor, as such, will have any liability for any obligations of the Company, any Existing Guarantor or any other Additional Guarantor under the Securities, the Indenture or the Guarantees, or for any claim based on,
in respect of, or by reason of, such obligations or their creation. Each Holder of Securities, by accepting a Security, waives and releases the Company, each Existing Guarantor and each Additional Guarantor from all such liability. The waiver and
release are part of the consideration for issuance of the Guarantee by the Additional Guarantors. 
 6. GOVERNING LAW.
THIS EIGHTH SUPPLEMENTAL INDENTURE AND THE GUARANTEES HEREUNDER SHALL BE GOVERNED BY, AND CONSTRUED IN ACCORDANCE WITH, THE LAWS OF THE STATE OF NEW YORK. 
 7. Counterparts. This Eighth Supplemental Indenture may be executed in any number of counterparts, each of which shall be deemed an original; but all such counterparts shall together constitute but
one and the same instrument. 
 8. Effect of Headings. The Section headings herein are for convenience only and shall not
affect the construction hereof. 
 9. Trustee. The Trustee shall not be responsible in any manner whatsoever for or in
respect of the validity or sufficiency of this Eighth Supplemental Indenture or for or in respect of the recitals contained herein, all of which recitals are made solely by the Additional Guarantors, the Existing Guarantors and the Company.

 IN WITNESS WHEREOF, the parties hereto have caused this Eighth Supplemental Indenture to be duly executed,
all as of the day and year first above written. 
  

			
	EXPRESS SCRIPTS HOLDING COMPANY
		
	By:	 	 /s/ Keith J. Ebling

	Name:	 	Keith J. Ebling
	Title:	 	Executive Vice President, General Counsel, and Secretary

 EXISTING GUARANTORS 

 

			
	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 Express Scripts Holding Company Eighth 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.

	 PRIORITY HEALTHCARE.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 Express Scripts Holding Company Eighth 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 Express Scripts Holding Company Eighth Supplemental Indenture] 

 ADDITIONAL GUARANTORS 

 

					
	MEDCO HEALTH SOLUTIONS, INC.
	ACCREDO HEALTH, INCORPORATED
	ACCREDO HEALTH GROUP, INC.
	MEDCO HEALTH SERVICES, INC.
		
	By:	 	 /s/ Keith J. Ebling

		 	Name:	 	Keith J. Ebling
		 	Title:	 	Vice President

 [Signature Page to Express Scripts Holding Company Eighth Supplemental Indenture] 

					
	WELLS FARGO BANK, NATIONAL ASSOCIATION, AS TRUSTEE
		
	By:	 	 /s/ Richard Prokosch

		 	Name:	 	Richard Prokosch
		 	Title:	 	Vice President

 [Signature Page to Express Scripts Holding Company Eighth Supplemental Indenture]Eighth Supplemental Indenture

 Exhibit 4.2 
 EIGHTH SUPPLEMENTAL INDENTURE 
 The Eighth Supplemental Indenture (this
“Eighth Supplemental Indenture”), dated as of April 2, 2012, among Express Scripts, Inc., a corporation duly organized and existing under the laws of the State of Delaware (the “Company”), the Guarantors listed
as signatories hereto (each, an “Existing Guarantor” and collectively, the “Existing Guarantors”), Medco Health Solutions, Inc., a Delaware corporation, and its subsidiaries listed as signatories hereto (each, an
“Additional Guarantor,” and, collectively, the “Additional Guarantors”) and Union Bank, N.A., a 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, the Existing Guarantors and the Trustee are parties to the indenture, dated as of June 9, 2009 (the “Base Indenture”), as supplemented by the First Supplemental
Indenture thereto, dated as of June 9, 2009 (the “First Supplemental Indenture”), relating to the Company’s 5.250% Notes due 2012 (the “2012 Notes”), the Second Supplemental Indenture thereto, dated as of
June 9, 2009 (the “Second Supplemental Indenture”), relating to the Company’s 6.250% Notes due 2014 (the “2014 Notes”), the Third Supplemental Indenture thereto, dated as of June 9, 2009 (the
“Third Supplemental Indenture”), relating to the Company’s 7.250% Notes due 2019 (the “2019 Notes”), the Fourth Supplemental Indenture thereto, dated as of December 1, 2009 (the “Fourth
Supplemental Indenture”), to add subsidiary guarantees, the Fifth Supplemental Indenture thereto, dated as of April 26, 2011 (the “Fifth Supplemental Indenture”), to add subsidiary guarantees, the Sixth Supplemental
Indenture thereto, dated as of May 2, 2011 (the “Sixth Supplemental Indenture”), relating to the Company’s 3.125% Notes due 2016 (together with the 2012 Notes, the 2014 Notes and the 2019 Notes, the
“Notes”), and the Seventh Supplemental Indenture thereto, dated as of November 21, 2011 (together with the First Supplemental Indenture, the Second Supplemental Indenture, the Third Supplemental Indenture, the Fourth
Supplemental Indenture, the Fifth Supplemental Indenture and the Sixth Supplemental Indenture, the “Supplemental Indentures” and the Base Indenture as so supplemented, the “Indenture”), to add subsidiary guarantees;

 WHEREAS, each Additional Guarantor desires to provide a full and unconditional guarantee (the “Guarantee”)
of the obligations of the Company under the Notes, the Securities (as defined in the Indenture) and the Indenture on the terms and conditions set forth herein; 
 WHEREAS, the Company has complied with all conditions precedent provided for in the Base Indenture and each Supplemental Indenture relating to this Eighth Supplemental Indenture; and 

WHEREAS, pursuant to Section 901 of the Base Indenture and Section 7.1 of each of the First Supplemental Indenture, the Second
Supplemental Indenture, the Third Supplemental Indenture and the Sixth Supplemental Indenture, the Company, the Trustee and the Additional Guarantors are authorized to execute and deliver this Eighth Supplemental Indenture. 

NOW, THEREFORE, for good and valuable consideration, the receipt of which is acknowledged, each Additional Guarantor hereby guarantees
the Company’s obligations under the Securities as follows: 
 1. Capitalized Terms. Capitalized terms used herein
without definition shall have the meanings assigned to them in the Indenture. 
 2. Guarantee, Etc. Each Additional
Guarantor hereby agrees that from and after the date hereof it shall be a Guarantor under the Indenture and be bound by its terms thereof applicable to Guarantors and shall be entitled to all of the rights and subject to all of the obligations of a
Guarantor thereunder. 
 3. Ratification of Indenture; Supplemental Indenture Part of Indenture. The Indenture is in all
respects ratified and confirmed, and all terms, conditions and provisions thereof shall remain in full force and effect. This Eighth Supplemental Indenture shall form a part of the Indenture for all purposes, and every Holder of Securities
heretofore or hereafter authenticated and delivered shall be bound hereby. 
 4. Representations and Warranties. Each
Additional Guarantor hereby represents that (a) it is duly organized, validly existing and in good standing under the laws of the jurisdiction of its organization, (b) it has full power, authority and legal rights to execute and deliver
this Eighth Supplemental Indenture and to perform 

 
its obligations hereunder and under the Indenture, (c) the execution, delivery and performance by it of this Eighth Supplemental Indenture has been duly authorized by all necessary corporate
action, and no other proceedings or actions on the part of such Additional Guarantor are necessary therefor and (d) this Eighth Supplemental Indenture has been duly and validly executed and delivered by such Additional Guarantor and constitutes
a legal, valid and binding obligation of such Additional Guarantor, enforceable against such Additional Guarantor in accordance with its terms (subject to applicable bankruptcy, insolvency, receivership, reorganization, moratorium and other similar
laws of general applicability relating to or affecting creditors’ rights and to general equity principles). 
 5. No
Personal Liability of Directors, Officers, Employees or Stockholders. No director, officer, employee, member or stockholder of any Additional Guarantor, as such, will have any liability for any obligations of the Company, any Existing Guarantor
or any other Additional Guarantor under the Securities, the Indenture or the Guarantees, or for any claim based on, in respect of, or by reason of, such obligations or their creation. Each Holder of Securities, by accepting a Security, waives and
releases the Company, each Existing Guarantor and each Additional Guarantor from all such liability. The waiver and release are part of the consideration for issuance of the Guarantee by the Additional Guarantors. 

6. GOVERNING LAW. THIS EIGHTH SUPPLEMENTAL INDENTURE AND THE GUARANTEES HEREUNDER SHALL BE GOVERNED BY, AND CONSTRUED IN
ACCORDANCE WITH, THE LAWS OF THE STATE OF NEW YORK. 
 7. Counterparts. This Eighth Supplemental Indenture may be
executed in any number of counterparts, each of which shall be deemed an original; but all such counterparts shall together constitute but one and the same instrument. 
 8. Effect of Headings. The Section headings herein are for convenience only and shall not affect the construction hereof. 
 9. Trustee. The Trustee shall not be responsible in any manner whatsoever for or in respect of the validity or sufficiency of this Eighth Supplemental Indenture or for or in respect of the recitals
contained herein, all of which recitals are made solely by the Additional Guarantors, the Existing Guarantors and the Company. 

 IN WITNESS WHEREOF, the parties hereto have caused this Eighth Supplemental Indenture to be duly executed,
all as of the day and year first above written. 
  

			
	EXPRESS SCRIPTS, INC.
		
	By:	 	 /s/ Keith J. Ebling

	Name:	 	Keith J. Ebling
	Title:	 	Vice President

 EXISTING GUARANTORS 

 

			
	EXPRESS SCRIPTS HOLDING COMPANY
		
	By:	 	 /s/ Keith J. Ebling

	Name:	 	Keith J. Ebling
	Title:	 	Executive Vice President, General Counsel, and Secretary
	
	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 Express Scripts, Inc. Eighth 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 Express Scripts, Inc. Eighth 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 Express Scripts, Inc. Eighth Supplemental Indenture] 

 ADDITIONAL GUARANTORS 

 

					
	MEDCO HEALTH SOLUTIONS, INC.
	ACCREDO HEALTH, INCORPORATED
	ACCREDO HEALTH GROUP, INC.
	MEDCO HEALTH SERVICES, INC.
		
	By:	 	 /s/ Keith J. Ebling

		 	Name:	 	Keith J. Ebling
		 	Title:	 	Vice President

 [Signature Page to Express Scripts, Inc. Eighth Supplemental Indenture] 

					
	UNION BANK, N.A., AS TRUSTEE
		
	By:	 	 /s/ Rafael E. Miranda

		 	Name:	 	Rafael E. Miranda
		 	Title:	 	Vice President

 [Signature Page to Express Scripts, Inc. Eighth Supplemental Indenture]

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