Document:

EX-4.2

 

Exhibit 4.2

AMENDED AND RESTATED FIRST SUPPLEMENTAL INDENTURE

     AMENDED AND RESTATED FIRST SUPPLEMENTAL INDENTURE (the “Amended and Restated First
Supplemental Indenture”), effective as of January 11, 2008, by and among PETROBRAS
INTERNATIONAL FINANCE COMPANY, an exempted company incorporated with limited liability under the
laws of the Cayman Islands, having its principal office at 4th Floor, Harbour Place, 103
South Church Street, George Town, Grand Cayman, Cayman Islands (the “Company”), THE BANK OF
NEW YORK, a New York banking corporation, as Trustee hereunder (the “Trustee”), and
PETRÓLEO BRASILEIRO S.A. — PETROBRAS, a mixed capital company (sociedade de economia mista)
organized under the laws of Brazil, having its principal office at Avenida República do Chile, 65,
20035-900 Rio de Janeiro — RJ, Brazil (“Petrobras”).

W I T N E S S E T H:

     WHEREAS, the Company and the Trustee previously have entered into an indenture, dated as of
December 15, 2006 (the “Original Indenture”), as supplemented by a First Supplemental
Indenture dated as of November 1, 2007 (the “First Supplement”) providing for the issuance
of US$1,000,000,000 of the Company’s 5.875% Global Notes due 2018 (the “Original Notes”);

     WHEREAS, Section 9.01 of the Original Indenture provides that, subsequent to the execution of
the Original Indenture and subject to satisfaction of certain conditions, the Company and the
Trustee may enter into one or more indentures supplemental to the Original Indenture to add to,
change or eliminate any of the provisions of the Original Indenture in respect of one or more
series of Securities (as defined in the Original Indenture);

     WHEREAS, on the date hereof the Company intends to issue an additional US$750,000,000 of its
5.875% Global Notes due 2018 constituting Add On Notes (as defined in the Original Indenture but
referred to herein as the “Reopening Notes” and together with the Original Notes, being
collectively referred to herein as the “Notes”) pursuant to its existing Registration
Statement on Form F-3 (File No. 333-139459-01) (the “Registration Statement”), dated
December 18, 2006, the Prospectus Supplement dated January 8, 2008 and related Base Prospectus
dated December 18, 2006 (collectively, the “Offering Document”) and the Original Indenture,
as supplemented by this Amended and Restated First Supplemental Indenture dated the date hereof
(the “Amended and Restated First Supplemental Indenture” and together with the Original
Indenture and any further supplements thereto being collectively referred to herein as the
“Indenture”);

     WHEREAS, as contemplated in the Offering Document, the parties hereto intend the Reopening
Notes to be consolidated, form a single series and be fully fungible with the Original Notes all of
which shall have the terms and conditions contemplated in the Offering Document and the form of
Note attached hereto as Exhibit A hereto;

     WHEREAS, as contemplated in the Offering Document, Petrobras and the Trustee intend, in
connection with the issuance of the Reopening Notes, to (i) enter into an Amended and Restated
Standby Purchase Agreement, dated as of the date hereof in the form attached as

 

 

Exhibit B hereto (the “Amended and Restated Standby Purchase Agreement”), to provide
the holders of the Notes (the “Holders”) with assurances that, if the Company shall fail to
make all required payments of principal, interest or other amounts due in respect of the Notes and
the Indenture, Petrobras will purchase the rights of the Holders to receive such amounts in
consideration of the payment by Petrobras of an amount of funds equal to the amounts then owed
under the Indenture and the Notes, subject to the provisions thereof and (ii) grant Holders of the
Notes direct rights against Petrobras in respect of the Amended and Restated Standby Purchase
Agreement by Petrobras being a party to the Indenture as provided herein;

     WHEREAS, the Trustee has provided to the Company and Petrobras Statements of Eligibility under
the Trust Indenture Act of 1939, as amended, with respect to each of the Companies which have been
filed as exhibits to the Registration Statement;

     WHEREAS, the Company and Petrobras confirm that any and all conditions and requirements
necessary to make this Amended and Restated First Supplemental Indenture a valid, binding, and
legal instrument in accordance with the terms of the Indenture (including the requirements of
Section 2.01(b) of the First Supplement) have been performed, satisfied and fulfilled and the
execution and delivery of this Amended and Restated First Supplemental Indenture has been in all
respects duly authorized;

     WHEREAS, pursuant to Section 9.01 of the Indenture, the Trustee is authorized to execute and
deliver this Amended and Restated First Supplemental Indenture; and

     WHEREAS, the Company and Petrobras have requested that the Trustee execute and deliver this
Amended and Restated First Supplemental Indenture;

     NOW, THEREFORE, for and in consideration of the premises and the mutual covenants contained
herein and in the Indenture and for other good and valuable consideration, the receipt and
sufficiency of which are herein acknowledged, the Company, Petrobras and the Trustee hereby agree,
for the equal and ratable benefit of all Holders, as follows:

ARTICLE 1

DEFINITIONS

     Section 1.01. Defined Terms. All capitalized terms used but not defined herein shall have the
meanings ascribed to such terms in the Indenture, as supplemented and amended hereby. All
definitions in the Original Indenture shall be read in a manner consistent with the terms of this
Amended and Restated First Supplemental Indenture.

     Section 1.02. Additional Definitions. (a) For the benefit of the Holders of the Notes,
Section 1.01 of the Original Indenture shall be amended by adding the following new definitions:

          “Closing Date” means November 1, 2007, the closing date of the issuance of the Original Notes
and the effective closing date of the issuance of the Reopening Notes.

          “Comparable Treasury Issue” means the United States Treasury security or securities selected
by an Independent Investment Banker as having an actual or interpolated

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maturity comparable to the remaining term of Notes to be redeemed 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 such Notes.

          “Comparable Treasury Price” means, with respect to any Redemption Date, (1) the average of the
Reference Treasury Dealer Quotations for such Redemption Date, after excluding the highest and
lowest such Reference Treasury Dealer Quotation or (2) if the Trustee obtains fewer than four such
Reference Treasury Dealer Quotations, the average of all such quotations.

          “Default Rate” has the meaning set forth in Section 2.01(g) herein.

          “Denomination Currency” has the meaning set forth in Section 2.03(b) herein.

          “Independent Investment Banker” means one of the Reference Treasury Dealers appointed by the
Company.

          “Interest Period” means the period beginning on an Interest Payment Date and ending on the day
before the next Interest Payment Date, except that the first Interest Period shall be the period
beginning on the Closing Date and ending on the day before the next Interest Payment Date.

          “Judgment Currency” has the meaning set forth in Section 2.03(b) herein.

          “Lien” means any mortgage, pledge, lien, hypothecation, security interest or other charge or
encumbrance on any property or asset, including, without limitation, any equivalent created or
arising under applicable law.

          “Make Whole Amount” has the meaning set forth in Section 2.01(k) herein.

          “Material Subsidiary” means, as to any Person, any Subsidiary of such Person which, on any
given date of determination, accounts for more than 10% of Petrobras’ total consolidated assets, as
such total assets are set forth on the most recent consolidated financial statements of Petrobras
prepared in accordance with U.S. GAAP (or if Petrobras does not prepare financial statements in
U.S. GAAP, consolidated financial statements prepared in accordance with Brazilian generally
accepted accounting principles).

          “Offering Document” shall have the meaning set forth in the recitals to the Amended and
Restated First Supplemental Indenture.

          “Payment Account” has the meaning set forth in Section 2.01(h) herein.

          “Permitted Lien” means a:

     (a) Lien arising by operation of law, such as merchants’, maritime or other similar
Liens arising in the Company’s ordinary course of business or that of any Subsidiary or Lien
in respect of taxes, assessments or other governmental charges that are not yet delinquent
or that are being contested in good faith by appropriate proceedings;

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     (b) Lien arising from the Company’s obligations under performance bonds or surety
bonds and appeal bonds or similar obligations incurred in the ordinary course of business
and consistent with the Company’s past practice;

     (c) Lien arising in the ordinary course of business in connection with Indebtedness
maturing not more than one year after the date on which such Indebtedness was originally
incurred and which is related to the financing of export, import or other trade
transactions;

     (d) Lien granted upon or with respect to any assets hereafter acquired by the Company
or any Subsidiary to secure the acquisition costs of such assets or to secure Indebtedness
incurred solely for the purpose of financing the acquisition of such assets, including any
Lien existing at the time of the acquisition of such assets as long as the maximum amount so
secured shall not exceed the aggregate acquisition costs of all such assets or the aggregate
Indebtedness incurred solely for the acquisition of such assets, as the case may be;

     (e) Lien granted in connection with the Indebtedness of a Wholly-Owned Subsidiary
owing to the Company or another Wholly-Owned Subsidiary;

     (f) Lien existing on any asset or on any stock of any Subsidiary prior to the
acquisition thereof by the Company or any Subsidiary as long as such Lien is not created in
anticipation of such acquisition;

     (g) Lien existing as of the date of the Indenture;

     (h) Lien resulting from the Indenture or the Amended and Restated Standby Purchase
Agreement;

     (i) Lien incurred in connection with the issuance of debt or similar securities of a
type comparable to those already issued by the Company, on amounts of cash or cash
equivalents on deposit in any reserve or similar account to pay interest on such securities
for a period of up to 24 months as required by any Rating Agency as a condition to such
Rating Agency rating such securities investment grade or as is otherwise consistent with
market conditions at such time, as such conditions are satisfactorily demonstrated to the
Trustee;

     (j) Lien granted or incurred to secure any extension, renewal, refinancing, refunding
or exchange (or successive extensions, renewals, refinancings, refundings or exchanges), in
whole or in part, of or for any Indebtedness secured by Lien referred to in paragraphs (a)
through (i) above (but not paragraph (c)), provided that such Lien does not extend to any
other property, the principal amount of the Indebtedness secured by such Lien is not
increased, and in the case of paragraphs (a), (b), and (c), the obligees meet the
requirements of such paragraphs; and

     (k) Lien in respect of Indebtedness the principal amount of which in the aggregate,
together with all Liens not otherwise qualifying as the Company’s Permitted Liens pursuant
to clauses (a) through (j) of this definition, does not exceed 15% of the

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Company’s consolidated total assets (as determined in accordance with U.S. GAAP) at any
date as at which the Company’s balance sheet is prepared and published in accordance with
applicable Law.

          “Reference Treasury Dealer” means each of Citigroup Global Markets Inc., HSBC Securities (USA)
Inc., BNP Paribas Securities Corp. or their affiliates which are primary United States government
securities dealers and two other leading primary United States government securities dealers in New
York City reasonably designated by the Company; provided, however, that if any of the foregoing
shall cease to be a primary United States government securities dealer in New York City (a “Primary
Treasury Dealer”), the Company shall substitute therefore another Primary Treasury Dealer.

          “Reference Treasury Dealer Quotation” 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 3:30 pm New York time on the
third business day preceding such redemption date.

          “Treasury Rate” means, with respect to any Redemption Date, the rate per annum equal to the
semiannual equivalent yield to maturity or interpolated maturity (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 2

TERMS OF THE NOTES

     Section 2.01. General. In accordance with Section 3.01 of the Original Indenture, the
following terms relating to the Notes are hereby established:

          (a) Title: The Notes shall constitute a single series of Securities having the title “5.875%
Global Notes due 2018.”

          (b) Aggregate Amount: The aggregate principal amount of the Reopening Notes that may be
authenticated and delivered under the Amended and Restated First Supplemental Indenture shall be
US$750,000,000 for a total aggregate principal amount of the Notes of US$1,750,000,000. As
provided in the Original Indenture, the Company may, from time to time, without the consent of the
Holders of Notes, issue additional Add On Notes having identical terms (including CUSIP, ISSN and
other relevant identifying characteristics as the Notes), so long as, on the date of issuance of
such Add On Notes: (i) no Default or Event of Default shall have occurred and then be continuing,
or shall occur as a result of the issuance of such Add On Notes, (ii) such Add On Notes shall rank
pari passu with the Notes and shall have identical terms, conditions and benefits as the Notes and
be part of the same series as the Notes, (iii) the Company and the Trustee shall have executed and
delivered a further supplemental indenture to the Indenture providing for the issuance of such Add
On Notes and reflecting such amendments to the Indenture as may be required to reflect the increase
in the aggregate principal amount of the Notes resulting from the issuance of the Add On Notes,
(iv) Petrobras and the

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Trustee shall have executed and delivered an amended Standby Purchase Agreement reflecting the
increase in the aggregate principal amount of the Notes resulting from the issuance of the Add On
Notes and (v) the Trustee shall have received all such opinions and other documents as it shall
have requested, including an Opinion of Counsel stating that such Add On Notes are authorized and
permitted by the Indenture and all conditions precedent to the issuance of such Add On Notes have
been complied with by the Company and Petrobras. All Add On Notes issued hereunder will, when
issued, be considered Notes for all purposes hereunder and will be subject to and take the benefit
of all of the terms, conditions and provisions of this Indenture.

          (c) Ranking: The Notes (including any additional Add On Notes) shall be general senior
unsecured and unsubordinated obligations of the Company and shall at all times rank pari passu
among themselves and at least equal in right of payment with all of the Company’s other present and
future unsecured and unsubordinated obligations from time to time outstanding that are not, by
their terms, expressly subordinated in right of payment to the Notes.

          (d) Maturity: The entire outstanding principal of the Notes shall be payable in a single
installment on March 1, 2018 (the “Stated Maturity”). No payments in respect of the
principal of the Notes shall be paid prior to the Stated Maturity except in the case of the
occurrence of an Event of Default and acceleration of the aggregate outstanding principal amount of
the Notes, upon redemption prior to the Stated Maturity pursuant to Section 11.08 of the Original
Indenture or pursuant to 2.01(l) and (m) hereof.

          (e) Interest: Interest shall accrue on the Notes at the rate of 5.875% per annum until all
required amounts due in respect of the Notes have been paid. All interest shall be paid by the
Company to the Trustee and distributed by the Trustee in accordance with this Indenture
semiannually in arrears on March 1 and September 1 of each year (or, as provided in the Original
Indenture, if such date is not a Business Day, the next succeeding Business Day following such day)
during which any portion of the Notes shall be Outstanding (each, an “Interest Payment
Date”), commencing on March 1, 2008, to the Person in whose name a Note is registered at the
close of business on the preceding Regular Record Date (which shall mean, with respect to any
payment to be made on an Interest Payment Date, the Business Day that is ten Business Days prior to
such Interest Payment Date.) As provided in the Original Indenture, (i) interest shall be
calculated based on a 360-day year of twelve 30-day months, (ii) payment of principal and interest
and other amounts on the Notes will be made at the Corporate Trust Office of the Trustee in New
York City, or such other paying agent office in the United States as the Company appoints, in the
form provided for in Section 10.08 of the Original Indenture, (iii) all such payments to the
Trustee shall be made by the Company by depositing immediately available funds in U.S. dollars one
Business Day prior to the relevant Interest Payment Date to the Payment Account and (iv) so long as
any of the Notes remain Outstanding, the Company shall maintain a paying agent in New York City.

          (f) Default Rate: Upon the occurrence and during the continuation of an Event of Default, (i)
interest on the outstanding principal amount of the Notes shall accrue on the Notes at a rate equal
to 1.0% per annum above the interest rate on the Notes at that time (the “Default Rate”)
and (ii) to the fullest extent permitted by law, interest shall accrue on the amount of any
interest, fee, Additional Amounts, or other amount payable under the Indenture and the

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Notes that is not paid when due, from the date such amount was due until such amount shall be
paid in full, excluding the date of such payment, at the Default Rate.

          (h) Payment Account: Until the Notes and all accounts due in respect thereof have been paid
in full, the Trustee shall continue to maintain the special purpose non-interest bearing trust
account established pursuant to the First Supplement (the “Payment Account”) into which
all payments required to be made by the Company under or with respect to the Notes shall be
deposited. The Company agrees that the Payment Account shall continue to be maintained in the name
of the Trustee and under its sole dominion and control (acting on behalf of the Holders of the
Notes) and used solely to make payments of principal, interest and other amounts from time to time
due and owing on, or with respect to, the Notes. No funds contained in the Payment Account shall
be used for any other purpose or in any manner not expressly provided for herein nor shall the
Company or any other Person have an interest therein or amounts on deposit therein. All amounts on
deposit in the Payment Account on any Interest Payment Date after the Trustee has paid all amounts
due and owing to the holders of the Notes as of such Interest Payment Date shall be retained in the
Payment Account and used by the Trustee to pay any amounts due and owing to the Holders of the
Notes on the next succeeding Interest Payment Date.

          (i) Form and Denomination: The Notes shall be issuable in whole in the registered form of one
or more Global Notes (without coupons), in minimum denominations of US$2,000 and integral multiples
of US$1,000 in excess thereof, and shall be transferable in integral multiples of US$2,000 and
integral multiples of US$1,000 in excess thereof and the Depository for such Global Notes shall be
The Depository Trust Company, New York, New York.

          (j) Amended and Restated Standby Purchase Agreement: The Notes shall have the benefit of the
Amended and Restated Standby Purchase Agreement in the manner provided in Article 3 of this Amended
and Restated First Supplemental Indenture.

          (k) Rating: The Notes can be issued without the requirement that they have any rating from a
nationally recognized statistical rating organization.

          (l) Optional Early Redemption. The Notes are subject to redemption at the Company’s option
before the Stated Maturity in whole or in part, upon not less than 30 but no more than 60 days’
notice, at a Redemption Price equal to the greater of (A) 100% of the principal amount of such
Notes and (B) the sum of the present values of the remaining scheduled payments of principal and
interest thereon (exclusive of interest accrued to the date of redemption) discounted to the
Redemption Date on a semiannual basis (assuming a 360-day year consisting of twelve 30-day months)
at, in each case, the Treasury Rate plus 25 basis points (the “Make Whole Amount”), plus in each
case, accrued interest on the principal amount of such Notes to (but not including) the date of
redemption.

          (m) Early Redemption Solely for Tax Reasons. Pursuant to Section 11.08 of the Original
Indenture, the Notes may be redeemed at the option of the Company, in whole but not in part, at any
time at a Redemption Price equal to the principal amount thereof plus accrued interest to the date
fixed for redemption if as a result of any change in or amendment to the laws

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or regulations or ruling promulgated thereunder of the jurisdiction in which the Company is
incorporated (or, in the case of a successor Person to the Company, of the jurisdiction in which
such successor Person is organized or any political subdivision or taxing authority thereof or
therein) or any change in the official application or interpretation of such laws, regulations or
rulings, or any change in the official application of or interpretation of, or any execution of or
amendment to, any treaty or treaties affecting taxation to which such jurisdiction or such
political subdivision or taxing authority (or such other jurisdiction or political subdivision or
taxing authority) is a party, which change, execution or amendment becomes effective on or after
the date hereof (or in the case of a successor Person to the Company, the date on which such
successor Person became such pursuant to Section 8.01 and 8.02 of the Original Indenture), the
Company would be required to pay Additional Amounts pursuant to Section 10.10 of the Original
Indenture. For purposes of Section 11.08 of the Original Indenture, the reincorporation of the
Company shall be treated as the adoption of a successor entity, provided, however, that redemption
under Section 11.08 of the Original Indenture shall not be available if the reincorporation was
performed in anticipation of a change in, execution of or amendment to any laws or treaties or the
official application or interpretation of any laws or treaties of such new jurisdiction of
incorporation that would result in an obligation to pay Additional Amounts.

          (n) Conversion: The Notes will not be convertible into, or exchangeable for, any other
securities.

     Section 2.02. Amendments to Article Five Relating to Events of Default. (a) Restated
Events of Default: As it applies to the Notes, Section 5.01 of the Original Indenture shall be
amended to read in its entirety as follows:

     “Section 5.01 Events of Default

     “Event of Default,” wherever used herein with respect to the Notes, means any one of
the following events (whatever the reason for such Event of Default and whether it shall be
voluntary or involuntary or be effected by operation of law or pursuant to any judgment,
decree or order of any court or any order, rule or regulation of any administrative or
governmental body):

     1. The Company shall fail to make any payment in respect of principal on any of the
Notes whether on the Stated Maturity, upon redemption or prior to the Maturity or otherwise
in accordance with the terms of the Notes and this Indenture, non-payment of which shall
continue for a period of three calendar days and the Trustee shall not have otherwise
received such amounts from Petrobras under the Standby Purchase Agreement, or otherwise by
the end of such three calendar day period;

     2. The Company shall fail to make any payment in respect of any interest or other
amounts due on or with respect to the Notes (including Additional Amounts, if any) in
accordance with the terms of the Notes and this Indenture, non-payment of which shall
continue for a period of 30 calendar days and the Trustee shall not have otherwise received
such amounts from Petrobras under the Standby Purchase Agreement, or otherwise by the end of
such 30 calendar day period;

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     3. The Company or Petrobras shall fail to perform, or breach, any term, covenant,
agreement or obligation contained in this Indenture or the Standby Purchase Agreement and
such failure (other than any failure to make any payment under the Standby Purchase
Agreement, for which there is no cure) is either incapable of remedy or continues for a
period of 60 calendar days (inclusive of any time frame contained in any such term,
covenant, agreement or obligation for compliance thereunder) after there has been received
by the Company or Petrobras from the Trustee or the Holders of at least 25% in principal
amount of the Outstanding Securities of that series a written notice specifying such default
or breach and requiring it to be remedied and stating that such notice is a “Notice of
Default” hereunder;

     4. The maturity of any Indebtedness of the Company, Petrobras or any Material
Subsidiary in a total aggregate principal amount of US$100,000,000 or more is accelerated in
accordance with the terms of that Indebtedness, it being understood that prepayment or
redemption by the Company, Petrobras or the relevant Material Subsidiary of any Indebtedness
is not acceleration for this purpose;

     5. One or more final and non-appealable judgments or final decrees is entered against
the Company, Petrobras or any Material Subsidiary thereof involving in the aggregate a
liability (not theretofore paid or covered by insurance) of US$100,000,000 (or its
equivalent in another currency) or more, and all such judgments or final decrees shall not
have been vacated, discharged or stayed within 120 calendar days after the rendering
thereof;

     6. The Company, Petrobras or any Material Subsidiary thereof stops payment of, or is
generally unable to pay, its debts as and when they become due except (i) as is otherwise
expressly provided under this Indenture or the Standby Purchase Agreement, or (ii) in the
case of a winding-up, dissolution or liquidation for the purpose of and followed by a
consolidation, merger, conveyance or transfer, the terms of which shall have been approved
by a resolution of a meeting of the Holders;

     7. Proceedings are initiated against the Company, Petrobras or any Material Subsidiary
thereof under any applicable bankruptcy, reorganization, insolvency, moratorium or
intervention law or law with similar effect, or under any other law for the relief of, or
relating to, debtors, and any such proceeding is not dismissed or stayed within 90 days
after the entering of such proceeding, or an administrator, receiver, trustee, manager,
fiduciary, statutory manager, intervener or assignee for the benefit of creditors (or other
similar official) is appointed to take possession or control of, or a distress, execution,
attachment or sequestration or other process is levied, enforced upon, sued out or put in
force against, all or any material part of the undertaking, property, assets or revenues of
the Company, Petrobras or any Material Subsidiary thereof and is not discharged or removed
within 90 days;

     8. The Company, Petrobras or any Material Subsidiary thereof commences voluntarily or
consents to judicial, administrative or other proceedings relating to it under any
applicable bankruptcy, reorganization, insolvency, moratorium or intervention law or law
with similar effect, or under any other law for the relief of, or relating to, debtors, or

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makes or enters into any composition, concordata or other similar arrangement with its
creditors, or appoints or applies for the appointment of an administrator, receiver,
trustee, manager, fiduciary, statutory manager, intervener or assignee for the benefit of
creditors (or other similar official) to take possession or control of the whole or any
material part of its undertaking, property, assets or revenues, or takes any judicial,
administrative or other similar proceeding under any law for a readjustment or deferment of
its Indebtedness or any part of it;

     9. An effective resolution is passed for, or any authorized action is taken by any
court of competent jurisdiction, directing the winding-up, dissolution or liquidation of the
Company, Petrobras or any Material Subsidiary thereof (other than in any of the
circumstances referred to as exceptions in paragraph (6) above);

     10. Any event occurs that under the laws of any relevant jurisdiction has substantially
the same effect as any of the events referred to in any of paragraphs (6), (7), (8) or (9)
of this Section 5.01;

     11. This Indenture, the Notes, the Standby Purchase Agreement or any part thereof shall
cease to be in full force and effect or binding and enforceable against the Company or
Petrobras, it becomes unlawful for the Company or Petrobras to perform any material
obligation under this Indenture, the Notes or the Standby Purchase Agreement, or the Company
or Petrobras shall contest the enforceability of this Indenture, the Notes or the Standby
Purchase Agreement or deny that it has liability under this Indenture, the Notes or the
Standby Purchase Agreement;

     12. Petrobras fails to retain at least 51% direct or indirect ownership of the
outstanding voting and economic interests (equity or otherwise) of and in the Company.”

     Section 2.03. Amendments to Article 10 Relating to Covenants.

          (a) Statement of Officers as to Default and Notices of Events of Default: As it
applies to the Notes, Section 10.05 of the Original Indenture shall be amended by deleting the
second sentence in its entirety and replacing it with the following:

     “Within 10 calendar days (or promptly with respect to Events of Default pursuant to
Sections 5.01(4), 5.01(5), 5.01(6), 5.01(7), 5.01(8), 5.01(9) and 5.01(10) hereunder and in
any event no later than 10 calendar days) after the Company becomes aware or should
reasonably become aware of the occurrence of an Event of Default pursuant to Section 5.01
hereunder, the Company shall provide notice to the Trustee of such occurrence, accompanied by
an Officer’s Certificate of the Company setting forth the details thereof.”

          (b) Additional Covenants Applicable to the Notes: As it applies to the Notes, Article
10 of the Original Indenture shall be amended to include the following:

     “Section 10.11 Use of Proceeds.

     The Company will use the proceeds from the offer and sale of the Notes after the
deduction of any commissions principally for general corporate purposes, including the

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financing of the purchase of oil product imports and the repayment of existing
trade-related debt and intercompany loans. The Company may also lend the proceeds from the
offer and sale of the Notes to Petrobras for use for its general corporate purposes.

     Section 10.12 Negative Pledge

     So long as any Note remains Outstanding, the Company will not create or permit any
Lien, other than a Permitted Lien, on any of the Company’s assets to secure (a) any of the
Company’s Indebtedness or (b) the Indebtedness of any other Person, unless the Company
contemporaneously creates or permits such Lien to secure equally and ratably the Company’s
obligations under the Notes and this Indenture or the Company provides such other security
for the Notes as is duly approved by a resolution of the Holders of the Notes in accordance
with this Indenture. In addition, the Company will not allow any of the Company’s
Subsidiaries to create or permit any Lien, other than a Permitted Lien, on any of its assets
to secure (a) any of the Company’s Indebtedness, (b) any of its own Indebtedness or (c) the
Indebtedness of any other Person, unless it contemporaneously creates or permits the Lien to
secure equally and ratably the Company’s obligations under the Notes and this Indenture or
the Company provides such other security for the Notes as is duly approved by a resolution
of the Holders of the Notes in accordance with the Indenture.

     Section 10.13 Currency Rate Indemnity. (a) The Company shall (to the extent
lawful) indemnify the Trustee and the Holders of the Notes and keep them indemnified
against:

     (i) in the case of nonpayment by the Company of any amount due to the Trustee, on
behalf of the Holders of the Notes, under the Indenture any loss or damage incurred by any
of them arising by reason of any variation between the rates of exchange used for the
purposes of calculating the amount due under a judgment or order in respect thereof and
those prevailing at the date of actual payment by the Company; and

     (ii) any deficiency arising or resulting from any variation in rates of exchange
between (i) the date as of which the local currency equivalent of the amounts due or
contingently due under the Indenture or in respect of the Notes is calculated for the
purposes of any bankruptcy, insolvency or liquidation of the Company, and (ii) the final
date for ascertaining the amount of claims in such bankruptcy, insolvency or liquidation.
The amount of such deficiency shall be deemed not to be increased or reduced by any
variation in rates of exchange occurring between the said final date and the date of any
bankruptcy, insolvency or liquidation or any distribution of assets in connection therewith.

     (b) The Company agrees that, if a judgment or order given or made by any court for the
payment of any amount in respect of its obligations hereunder is expressed in a currency
(the “Judgment Currency”) other than U.S. dollars (the “Denomination
Currency”), it will indemnify the relevant Holder and the Trustee against any deficiency
arising or resulting from any variation in rates of exchange between the date at which the
amount in the Denomination Currency is notionally converted into the amount in the

11

 

Judgment Currency for the purposes of such judgment or order and the date of actual
payment thereof.

     (c) The above indemnities shall constitute separate and independent obligations of the
Company from its obligations under the Indenture, will give rise to separate and independent
causes of action, will apply irrespective of any indulgence granted from time to time and
will continue in full force and effect notwithstanding any judgment or the filing of any
proof or proofs in any bankruptcy, insolvency or liquidation of the Company for a liquidated
sum or sums in respect of amounts due under the Indenture or the Notes.”

     Section 2.04. Application of the Article of the Indenture Regarding Defeasance and Covenant
Defeasance. The provisions of Sections 14.01, 14.02 and 14.03 of the Original Indenture shall
apply to the Notes.

ARTICLE 3

AMENDED AND RESTATED STANDBY PURCHASE AGREEMENT

     Section 3.01. Execution. The Trustee is hereby authorized and directed to execute and deliver
the Amended and Restated Standby Purchase Agreement and to perform all of its duties and
obligations thereunder.

     Section 3.02. Enforcement. The Trustee shall enforce the provisions of the Amended and
Restated Standby Purchase Agreement against Petrobras in accordance with the terms thereof and the
terms of the Indenture and Petrobras, by execution of this Amended and Restated First Supplemental
Indenture, and by so agreeing to become a party to the Indenture, agrees that each Holder of the
Notes shall have direct rights under the Amended and Restated Standby Purchase Agreement as if it
were a party thereto.

     Section 3.03. Petrobras hereby (i) acknowledges and agrees to be bound by the provisions of
Sections 1.08 and 3.14 of the Original Indenture and (ii) confirms that (A) its obligations under
the Amended and Restated Standby Purchase Agreement shall be issued pursuant to the Indenture and
(B) it intends for the Holders of the Notes, in addition to those rights under the Amended and
Restated Standby Purchase Agreement as provided therein, to be entitled to the benefits of the
Indenture with respect to their rights against Petrobras under the Amended and Restated Standby
Purchase Agreement.

     Section 3.04. Definition of the Term “Securities.” For all purposes relating to the Notes,
the term “Securities” in Section 1.01 of the Original Indenture shall be amended by inserting the
following at the end thereof: “All references herein to any Securities shall be deemed to include
the rights of the Holder thereof under any standby purchase agreement or guarantee arrangement
entered into by Petrobras with the Trustee in connection with the issuance of such Securities
pursuant to Section 3.14 hereof, which are an integral part of such Securities.”

ARTICLE 4

MISCELLANEOUS

12

 

     Section 4.01. Effect of the Amended and Restated First Supplemental Indenture. This Amended
and Restated First Supplemental Indenture supplements the Indenture and shall be a part, and
subject to all the terms, thereof. The Original Indenture, as supplemented and amended by this
Amended and Restated First Supplemental Indenture, is in all respects ratified and confirmed, and
the Original Indenture and this Amended and Restated First Supplemental Indenture shall be read,
taken and construed as one and the same instrument. All provisions included in this Amended and
Restated First Supplemental Indenture supersede any conflicting provisions included in the Original
Indenture unless not permitted by law. The provisions of this Amended and Restated First
Supplemental Indenture are intended to apply solely to the Notes and the Holders thereof and shall
not apply to any future issuance of securities by the Company (other than any Add On Notes as
provided herein) and all references to provisions of the Original Indenture herein amended and
restated or otherwise modified shall have effect solely with respect to the Notes contemplated in
this Amended and Restated First Supplemental Indenture. The Trustee accepts the trusts created by
the Original Indenture, as supplemented by this Amended and Restated First Supplemental Indenture,
and agrees to perform the same upon the terms and conditions of the Original Indenture, as
supplemented by this Amended and Restated First Supplemental Indenture.

     Section 4.02. Governing Law. This Amended and Restated First Supplemental Indenture shall be
governed by, and construed in accordance with, the laws of the State of New York.

     Section 4.03. Trustee Makes No Representation. The Trustee shall not be responsible in any
manner whatsoever for or in respect of the validity or sufficiency of this Amended and Restated
First Supplemental Indenture or for or in respect of the recitals contained herein, all of which
are made solely by the Company and Petrobras.

     Section 4.04. Effect of Headings. The section headings herein are for convenience only and
shall not affect the construction of this Amended and Restated First Supplemental Indenture.

     Section 4.05. Counterparts. The parties may sign any number of copies of this Amended and
Restated First Supplemental Indenture. Each signed copy shall be an original, but all of them
shall represent the same agreement.

[SIGNATURE PAGE TO FOLLOW IMMEDIATELY]

13

 

          IN WITNESS WHEREOF, the parties have caused this Amended and Restated First Supplemental
Indenture to be duly executed by their respective officers thereunto duly authorized as of the day
and year first above written.

	 	 	 	 	 
	 	 	PETROBRAS INTERNATIONAL FINANCE COMPANY
	 
	 	 	 	 
	 

	 	By:	 	 
	 

	 	 	 	 
	 

	 	 	 	Name:
	 

	 	 	 	Title:
	 
	 	 	 	 
	 	 	PETRÓLEO BRASILEIRO S.A. — PETROBRAS
	 
	 	 	 	 
	 

	 	By:	 	 
	 

	 	 	 	 
	 

	 	 	 	Name:
	 

	 	 	 	Title:
	 
	 	 	 	 
	 	 	WITNESSES:
	 
	 	 	 	 
	 

	 	1. 	 	 
	 

	 	 	 	 
	 

	 	 	 	Name:
	 
	 	 	 	 
	 

	 	2.	 	 
	 

	 	 	 	 
	 

	 	 	 	Name:

Amended and Restated First Supplemental Indenture

 

 

	 	 	 	 	 
	 	 	THE BANK OF NEW YORK, as Trustee
	 
	 	 	 	 
	 

	 	By:	 	 
	 

	 	 	 	 
	 

	 	 	 	Name:
	 

	 	 	 	Title:
	 
	 	 	 	 
	 	 	WITNESSES:
	 
	 	 	 	 
	 

	 	1. 	 	 
	 

	 	 	 	 
	 

	 	 	 	Name:
	 
	 	 	 	 
	 

	 	2. 	 	 
	 

	 	 	 	 
	 

	 	 	 	Name:

Amended and Restated First Supplemental Indenture

 

 

	 	 	 	 	 	 	 
	STATE OF NEW YORK

	 	 	)	 	 	 
	 

	 	 	)	 	 	ss:
	COUNTY OF NEW YORK

	 	 	)	 	 	 

          On this       day of January, 2008 before me, a notary public within and for said county,
personally appeared                                         , to me personally known who being duly sworn, did say that
                                         is a             
                             of The Bank of New York, one of the persons described
in and which executed the foregoing instrument, and acknowledge said instrument to be the free act
and deed of said corporation.

          On this       day of January, 2008, before me personally came                                          and
                                         to me personally known, who being by me sworn, did depose and say that they
signed their names to the foregoing instrument as witnesses.

	 	 	 
	 	 	 
	 
	 	Notary Public

Amended and Restated First Supplemental Indenture

 

 

	 	 	 	 	 	 	 
	STATE OF NEW YORK

	 	 	)	 	 	 
	 

	 	 	)	 	 	ss:
	COUNTY OF NEW YORK

	 	 	)	 	 	 

          On this       day of January, 2008, before me personally came                                         , to me
known, who, being by me duly sworn, did depose and say that he is the Attorney-in-Fact of Petrobras
International Finance Company — PIFCo, a corporation described in and which executed the foregoing
instrument and acknowledge that said instrument to be the free act and deed of said entity.

          On this       day of January, 2008, before me personally came                                         , to me
known, who, being by me duly sworn, did depose and say that he is the Attorney-in-Fact of Petróleo
Brasileiro S.A. — Petrobras, a corporation described in and which executed the foregoing instrument
and acknowledge that said instrument to be the free act and deed of said entity.

          On this       day of January, 2008, before me personally came                                          and
                                         to me personally known, who being by me sworn, did depose and say that they
signed their names to the foregoing instrument as witnesses.

[Notarial Seal]

	 	 	 
	 	 	 
	 

	 	Notary Public
	 

	 	COMMISSION EXPIRES

Amended and Restated First Supplemental Indenture

 

 

Exhibit A

Form of 5.875% Global Note due 2018

GLOBAL NOTE

THIS NOTE IS A GLOBAL NOTE WITHIN THE MEANING OF THE INDENTURE HEREINAFTER REFERRED TO AND IS
REGISTERED IN THE NAME OF A DEPOSITORY OR A NOMINEE THEREOF. THIS NOTE MAY NOT BE EXCHANGED IN
WHOLE OR IN PART FOR A NOTE REGISTERED, AND NO TRANSFER OF THIS NOTE IN WHOLE OR IN PART MAY BE
REGISTERED, IN THE NAME OF ANY PERSON OTHER THAN SUCH DEPOSITORY OR ITS NOMINEE EXCEPT IN THE
LIMITED CIRCUMSTANCES DESCRIBED IN THE INDENTURE.

UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST
COMPANY TO THE ISSUER OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT AND SUCH
CERTIFICATE ISSUED IN EXCHANGE FOR THIS CERTIFICATE IS REGISTERED IN THE NAME OF CEDE & CO., OR
SUCH OTHER NAME AS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY, ANY TRANSFER,
PLEDGE OR OTHER USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL, SINCE THE
REGISTERED OWNER HEREOF, CEDE & CO., HAS AN INTEREST HEREIN.

 

 

PETROBRAS INTERNATIONAL FINANCE COMPANY

5.875% GLOBAL NOTES DUE 2018

No.

CUSIP No.: 71645WAM3

ISIN No.: US71645WAM38

Common Code: 032961614

	 	 	 
	 

	 	Principal Amount: US$
	 

	 	Issuance Date: January 11, 2008

          This Note is one of a duly authorized issue of notes of PETROBRAS INTERNATIONAL FINANCE
COMPANY, an exempted company with limited liability organized under the laws of the Cayman Islands
(the “Issuer”), designated as its 5.875% Global Notes Due 2018 (the “Notes”),
issued in an initial aggregate principal amount of US$                     under the Amended and
Restated First Supplemental Indenture (the “Amended and Restated First Supplemental
Indenture”), effective as of January 11, 2008, by and among the Issuer, The Bank of New York, a
New York banking corporation, as Trustee (the “Trustee”), and Petróleo Brasileiro S.A. -
PETROBRAS, a mixed capital company (sociedade de economia mista) organized under the laws of Brazil
(“Petrobras”), to the Indenture, dated as of December 15, 2006 (the “Original
Indenture”, and as supplemented by the Amended and Restated First Supplemental Indenture and
any further supplements thereto with respect to the Notes, the “Indenture”), by and among
the Issuer and the Trustee. Reference is hereby made to the Indenture for a statement of the
respective rights, limitations of interests, benefits, obligations and duties thereunder of the
Issuer, the Trustee and the Holders, and of the terms upon which the Notes are, and are to be,
authenticated and delivered. All capitalized terms used in this Note which are defined in the
Indenture and not otherwise defined herein shall have the meanings assigned to them in the
Indenture.

          The Issuer, for value received, hereby promises to pay to Cede & Co. or its registered
assigns, as nominee of The Depository Trust Company (“DTC”) and the Holder of record of
this Note, the principal amount specified above in U.S. dollars on March 1, 2018 (or earlier as
provided for in the Indenture) upon presentation and surrender hereof, at the office or agency of
the Trustee referred to below.

          As provided for in the Indenture, the Issuer promises to pay interest on the outstanding
principal amount hereof, from the Closing Date, semi-annually on March 1 and September 1 of each
year (or if such date is not a Business Day, the next succeeding Business Day following such day),
commencing March 1, 2008 (each such date, an “Interest Payment Date”), at a rate equal to
5.875% per annum. Interest payable, and punctually paid or duly provided for, on this Note on any
Interest Payment Date will, as provided in the Indenture, be paid in U.S. dollars to the Person in
whose name this Note (or one or more predecessor Notes) is registered at the close of business on
the relevant Regular Record Date for such interest payment.

 

 

          Payment of the principal of and interest on this Note will be payable by wire transfer to a
U.S. dollar account maintained by the Holder of this Note as reflected in the Security Register of
the Trustee. In the event the date for any payment of the principal of or interest on any Note is
not a Business Day, then payment will be made on the next Business Day with the same force and
effect as if made on the nominal date of any such date for such payment and no additional interest
will accrue on such payment as a result of such payment being made on the next succeeding Business
Day. Interest accrued with respect to this Note shall be calculated based on a 360-day year of
twelve 30-day months.

          The Notes are subject to redemption by the Issuer on the terms and conditions specified in the
Indenture.

          This Note does not purport to summarize the Indenture, and reference is made to the Indenture
for information with respect to the respective rights, limitations of interests, benefits,
obligations and duties thereunder of the Issuer, the Trustee and the Holders.

          If an Event of Default shall occur and be continuing, the outstanding principal amount of all
the Notes may become or may be declared due and payable in the manner and with the effect provided
in the Indenture.

          Modifications of the Indenture may be made by the Issuer and the Trustee only to the extent
and in the circumstances permitted by the Indenture.

          The Notes shall be issued only in fully registered form, without coupons. Notes shall be
issued in the form of beneficial interests in one or more global securities in denominations of
US$2,000 and integral multiples of US$1,000 in excess thereof.

          Prior to and at the time of due presentment of this Note for registration of transfer, the
Issuer, the Trustee and any agent of the Issuer or the Trustee may treat the Person in whose name
this Note is registered as the owner hereof for all purposes, whether or not this Note is overdue,
and neither the Issuer, the Trustee nor any agent thereof shall be affected by notice to the
contrary.

[REMAINDER OF PAGE INTENTIONALLY LEFT BLANK]

 

 

          Unless the certificate of authentication hereon has been duly executed by the Trustee by
manual signature, this Note shall not be entitled to any benefit under the Indenture, or be valid
or obligatory for any purpose.

          THIS NOTE SHALL BE CONSTRUED IN ACCORDANCE WITH, AND GOVERNED BY, THE LAWS OF THE STATE OF NEW
YORK.

          IN WITNESS WHEREOF, the Issuer has caused this Note to be duly executed.

	 	 	 	 	 
	 	 	PETROBRAS INTERNATIONAL FINANCE COMPANY
	 
	 	 	 	 
	 

	 	By:	 	 
	 

	 	 	 	 
	 

	 	 	 	Name:
	 

	 	 	 	Title:
	 
	 	 	 	 
	 	 	WITNESSES:
	 

	 	1. 	 	 
	 

	 	 	 	 
	 

	 	 	 	Name:
	 

	 	2. 	 	 
	 

	 	 	 	 
	 

	 	 	 	Name:

 

 

	 	 	 	 	 	 	 
	STATE OF NEW YORK

	 	 	)	 	 	 
	 

	 	 	)	 	 	ss:
	COUNTY OF NEW YORK

	 	 	)	 	 	 

          On this      
day of January, 2008, before me personally came                     ,
to me known, who,
being by me duly sworn, did depose and say that he is the                    
                      of Petrobras
International Finance Company, a corporation described in and which executed the foregoing
instrument and acknowledges that said instrument to be the free act and deed of said entity.

          On this       day of
January, 2008, before me personally came                          
                and
                           
             
to me personally known, who being by me sworn, did depose and say that they signed their names to
the foregoing instrument as witnesses.

               [Notarial Seal]

	 	 	 
	 	 	 
	 

	 	Notary Public
	 

	 	COMMISSION EXPIRES

 

 

CERTIFICATE OF AUTHENTICATION

     This is one of the Securities of the series designated therein referred to in the within
mentioned Indenture.

Dated: January      , 2008

	 	 	 	 	 
	 	 	The Bank of New York
	 	 	As Trustee
	 
	 	 	 	 
	 

	 	By:	 	 
	 

	 	 	 	 
	 

	 	 	 	Name:
	 

	 	 	 	Title: Authorized Officer

 

 

ASSIGNMENT FORM

For value received

hereby sells, assigns and transfers unto

(Please insert social security or

other identifying number of assignee)

 

(Please print or type name and address,

including zip code, of assignee:)

the within Note and does hereby irrevocably constitute and appoint Attorney to transfer the Note on
the books of the Note Registrar with full power of substitution in the premises.

	 	 	 	 	 
	Date:

	 	Your Signature:	 	 
	 

	 	 	 	(Sign exactly as your name
	 

	 	 	 	appears on the face of this Note)

 

 

Exhibit B

Form of Standby Purchase AgreementEX-10.25

 

Exhibit 10.25

XANODYNE PHARMACEUTICALS, INC.

Form of Restricted Stock Unit Agreement

Granted Under 2007 Stock Incentive Plan

     1. Grant of Award.

     This Agreement evidences the grant by Xanodyne Pharmaceuticals, Inc., a Delaware corporation
(the “Company”) on ___, 20___(the “Grant Date”) to ___(the “Participant”) of
___restricted stock units of the Company (individually, an “RSU” and collectively, the
“RSUs”) on the terms provided herein and in the Company’s 2007 Stock Incentive Plan (the “Plan”).
Each RSU represents the right to receive one share of the common stock, $0.001 par value per share,
of the Company (“Common Stock”) as provided in this Agreement. The shares of Common Stock that are
issuable upon vesting of the RSUs are referred to in this Agreement as “Shares.”

     2. Vesting; Forfeiture.

          (a) This award shall vest as to (i) 33% of the original number of RSUs on the first
anniversary of the Grant Date, (ii) 33% of the original number of RSUs on the second anniversary of
the Grant Date, and (ii) 34% of the original number of RSUs on the third anniversary of the Grant
Date.

          (b) If the Participant’s employment with the Company terminates before the date upon which
this award is fully vested, any portion of this award that is not vested as of the date of such
termination shall be forfeited.

          (c) For purposes of this Agreement, employment with the Company shall include employment with
a parent or subsidiary of the Company.

     3. Distribution of Shares; Deferral of Delivery

          (a) The Company will distribute the Shares issuable with respect to vested RSUs to the
Participant on the earliest of (i) the third anniversary of the Grant Date, (ii) subject to Section
3(c), the Participant’s “separation of service” as defined in Section 409A of the Internal Revenue
Code of 1986 (the “Code”), and (iii) the date of a Change in Control Event (as defined in the Plan)
that constitutes a “change in the ownership or effective control of a corporation or a change in
the ownership of a substantial portion of the assets of a corporation”, as defined for purposes of
Section 409A of the Code. Neither the Company nor the Participant may accelerate or defer the
delivery of the Shares. For the sake of clarity, if a sale described in clause (iii) of the
preceding sentence occurs before this award is fully vested, then the Company will distribute the
Shares issuable with respect to RSUs that are not then vested on the date, if any, that such RSUs
subsequently vest.

          (b) The Company shall not be obligated to issue the Shares to the Participant unless the
issuance and delivery of such Shares shall comply with all relevant provisions of law and other
legal requirements including, without limitation, any applicable federal or state

 

 

securities laws and the requirements of any stock exchange upon which shares of Common Stock
may then be listed.

          (c) If the Participant is a “specified employee” within the meaning of Section 409A of the
Code, and if any issuance of Shares hereunder is subject to the rule under Section 409A(a)(2)(B)(i)
of the Code, then such issuance of Shares shall be delayed until the date that is six months and
one day after the Participant has a “separation from service” as defined in Section 409A of the
Code.

     4. Restrictions on Transfer.

     The Participant shall not sell, assign, transfer, pledge, hypothecate or otherwise dispose of,
by operation of law or otherwise (collectively “transfer”) any RSUs, or any interest therein,
except by will or the laws of descent and distribution.

     5. Dividend and Other Shareholder Rights.

     Except as set forth in the Plan, neither the Participant nor any person claiming under or
through the Participant shall be, or have any rights or privileges of, a stockholder of the Company
in respect of the Shares issuable pursuant to the RSUs granted hereunder until the Shares have been
delivered to the Participant.

     6. Provisions of the Plan.

     This Agreement is subject to the provisions of the Plan, a copy of which is furnished to the
Participant with this Agreement.

     7. Agreement in Connection with Initial Public Offering.

     The Participant agrees, in connection with the initial underwritten public offering pursuant
to an effective registration statement under the Securities Act, covering the offer and sale of the
Company’s common stock for the account of the Company to the public, (i) not to (a) offer, pledge,
announce the intention to sell, sell, contract to sell, sell any option or contract to purchase,
purchase any option or contract to sell, grant any option, right or warrant to purchase, or
otherwise transfer or dispose of, directly or indirectly, any shares of Common Stock or any other
securities of the Company or (b) enter into any swap or other agreement that transfers, in whole or
in part, any of the economic consequences of ownership of shares of Common Stock or other
securities of the Company, whether any transaction described in clause (a) or (b) is to be settled
by delivery of securities, in cash or otherwise, during the period beginning on the date of the
filing of such registration statement with the Securities and Exchange Commission and ending 180
days after the date of the final prospectus relating to the offering (plus up to an additional 34
days to the extent requested by the managing underwriters for such offering in order to address
Rule 2711(f) of the National Association of Securities Dealers, Inc. or any similar successor
provision), and (ii) to execute any agreement reflecting clause (i) above as may be requested by
the Company or the managing underwriters at the time of such offering. The Company may impose
stop-transfer instructions with respect to the shares of Common Stock or other securities subject
to the foregoing restriction until the end of the “lock-up” period.

-2-

 

     8. Withholding Taxes; No Section 83(b) Election.

          (a) No Shares will be delivered to the Participant unless and until the Participant pays to
the Company, or makes provision satisfactory to the Company for payment of, any federal, state or
local withholding taxes required by law to be withheld in respect of this option.

          (b) The Participant acknowledges that no election under Section 83(b) of the Internal Revenue
Code of 1986 may be filed with respect to this award.

     9. Miscellaneous.

          (a) No Rights to Employment. The Participant acknowledges and agrees that the vesting
of the RSUs is subject to the conditions set forth in Section 2 hereof, including continuing
service as an employee at the will of the Company (not through the act of being hired or purchasing
shares hereunder). The Participant further acknowledges and agrees that the transactions
contemplated hereunder and the vesting schedule set forth herein do not constitute an express or
implied promise of continued engagement as an employee or consultant for the vesting period, for
any period, or at all.

          (b) Severability. The invalidity or unenforceability of any provision of this
Agreement shall not affect the validity or enforceability of any other provision of this Agreement,
and each other provision of this Agreement shall be severable and enforceable to the extent
permitted by law.

          (c) Waiver. Any provision for the benefit of the Company contained in this Agreement
may be waived, either generally or in any particular instance, by the Board of Directors of the
Company.

          (d) Binding Effect. This Agreement shall be binding upon and inure to the benefit of
the Company and the Participant and their respective heirs, executors, administrators, legal
representatives, successors and assigns, subject to the restrictions on transfer set forth in
Section 4 of this Agreement.

          (e) Notice. All notices required or permitted hereunder shall be in writing and
deemed effectively given upon personal delivery or five days after deposit in the United States
Post Office, by registered or certified mail, postage prepaid, addressed to the other party hereto
at the address shown beneath his or its respective signature to this Agreement, or at such other
address or addresses as either party shall designate to the other in accordance with this Section
9(e).

          (f) Pronouns. Whenever the context may require, any pronouns used in this Agreement
shall include the corresponding masculine, feminine or neuter forms, and the singular form of nouns
and pronouns shall include the plural, and vice versa.

          (g) Entire Agreement. This Agreement and the Plan constitute the entire agreement
between the parties, and supersedes all prior agreements and understandings, relating to the
subject matter of this Agreement.

-3-

 

          (h) Amendment. This Agreement may be amended or modified only by a written instrument
executed by both the Company and the Participant.

          (i) Governing Law. This Agreement shall be construed, interpreted and enforced in
accordance with the internal laws of the State of Delaware without regard to any applicable
conflicts of laws.

          (j) Participant’s Acknowledgments. The Participant acknowledges that he or she: (i)
has read this Agreement; (ii) has been represented in the preparation, negotiation, and execution
of this Agreement by legal counsel of the Participant’s own choice or has voluntarily declined to
seek such counsel; (iii) understands the terms and consequences of this Agreement; (iv) is fully
aware of the legal and binding effect of this Agreement; and (v) understands that the law firm of
Wilmer Cutler Pickering Hale and Dorr LLP, is acting as counsel to the Company in connection with
the transactions contemplated by the Agreement, and is not acting as counsel for the Participant.

          (k) Unfunded Rights. The right of the Participant to receive Common Stock pursuant to
this Agreement is an unfunded and unsecured obligation of the Company. The Participant shall have
no rights under this Agreement other than those of an unsecured general creditor of the Company.

     IN WITNESS WHEREOF, the parties hereto have executed this Agreement as of the day and year
first above written.

	 	 	 	 	 
	 	XANODYNE PHARMACEUTICALS, INC.

 	 
	 	By:  	 	 
	 	 	Name:  	 	 
	 	 	Title:  	 	 
	 
	 	 	 
	 	
 	 
	 	[Name of Participant] 	 
	 	Address: 	 
	 

-4-

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