EX-4.2






Exhibit 4.2




EXECUTION VERSION




SECOND SUPPLEMENTAL INDENTURE




     SECOND SUPPLEMENTAL INDENTURE (the “Second Supplemental Indenture”), effective as of
February 11, 2009, by and among PETROBRAS INTERNATIONAL FINANCE COMPANY – PIFCO, 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 MELLON (formerly known
as 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”, and as supplemented by this Second
Supplemental Indenture and any further supplements thereto, the “Indenture”), providing for
the issuance from time to time of debt securities and debt warrants of the Company to be issued in
one or more series as provided in the Indenture;



     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 Indenture);



     WHEREAS, on the date hereof the Company intends to issue pursuant to its Registration
Statement on Form F-3 (File No. 333-139459-01) (the “Registration Statement”), dated
December 18, 2006, the Prospectus Supplement dated February 4, 2009 and related Base Prospectus
dated December 18, 2006 (collectively, the “Offering Document”) and the Indenture,
U.S.$1,500,000,000 of its 7.875% Global Notes due 2019, in the form attached as Exhibit A hereto
(the “Notes”), having the terms and conditions contemplated in the Offering Document as
provided for in the Original Indenture, as supplemented by this Second Supplemental Indenture;



     WHEREAS, as contemplated in the Offering Document, Petrobras and the Trustee intend, in
connection with the issuance of the Notes, to enter into a guaranty, dated as of the date hereof in
the form attached as Exhibit B hereto (the “Guaranty”), to provide for an unconditional and
irrevocable guaranty of the Notes by Petrobras;



     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, any and all conditions and requirements necessary to make this Second Supplemental
Indenture a valid, binding, and legal instrument in accordance with the terms of the Indenture have
been performed and fulfilled and the execution and delivery of this Second Supplemental Indenture
have been in all respects duly authorized;



     WHEREAS, pursuant to Section 9.01 of the Original Indenture, the Trustee is authorized to
execute and deliver this Second Supplemental Indenture; and



     WHEREAS, the Company and Petrobras have requested that the Trustee execute and deliver this
Second 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
Second 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 February 11, 2009.




          “Comparable Treasury Issue” means the United States Treasury security or securities selected
by an Independent Investment Banker as having an actual or interpolated maturity comparable to the
remaining term of 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(f) herein.




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




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




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          “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(c) 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(l) 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 Second
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;




     (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;



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     (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 Second Supplemental Indenture;




     (h)  Lien resulting from the Indenture or the Guaranty;




     (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 (d)), 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), (c) and (f) 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 Company’s
consolidated total assets (as determined in accordance with Reporting 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 HSBC Securities (USA) Inc. and J.P. Morgan
Securities Inc. or, in each case, 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.




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          “Regular Record Date” means one Business Day prior to any Interest Payment Date.




          “Reporting GAAP” means (i) generally accepted accounting principles in effect in the United
States of America applied on a basis consistent with the principles, methods, procedures and
practices in effect from time to time or (ii) International Financial Reporting Standards
(“IFRS”) as adopted by the International Accounting Standards Board (“IASB”) as from the
date the Guarantor adopts IFRS as its primary reporting or accounting standard in its reports filed
with the SEC pursuant to Section 13 or 15(d) of the Exchange Act.




          “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 series of Securities having the title “7.875% Global
Notes due 2019.”




          (b) Aggregate Amount: The aggregate principal amount of the Notes that may be initially
authenticated and delivered under the Second Supplemental Indenture shall be U.S.$1,500,000,000.
As provided in the Original Indenture, the Company may, from time to time, without the consent of
the Holders of Notes, issue 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 shall have executed and delivered and the Trustee shall have acknowledged an amended
Guaranty 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.




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          (c) Ranking: The Notes (including any 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 15, 2019 (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 7.875% 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 15 and September 15 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 September 15, 2009, 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 preceding the relevant 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 0.5% 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 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.




          (g) Payment Account: On the Closing Date, the Trustee shall establish (and shall promptly
notify the Company of the establishment of such account, including the relevant account numbers and
other relevant identifying details) and, until the Notes and all accounts due in respect thereof
have been paid in full, maintain a special purpose non-interest bearing trust account (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 be
maintained in the name of the Trustee and under its sole dominion and control



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(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.




          (h) 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 U.S.$2,000 and integral
multiples of U.S.$1,000 in excess thereof, and shall be transferable in integral multiples of
U.S.$2,000 and integral multiples of U.S.$1,000 in excess thereof and the Depository for such
Global Notes shall be The Depository Trust Company, New York, New York.




          (i) Guaranty: The Notes shall have the benefit of the Guaranty in the manner provided in
Article 3 of this Second Supplemental Indenture.




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




          (k) 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 50 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.




          (l) 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 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



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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.




          (m) 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 Guaranty, 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 Guaranty, or otherwise by the end of such 30 calendar
day period;




     3. The Company or Petrobras shall fail to perform, or breach, any term, covenant,
agreement or obligation contained in this Indenture or the Guaranty and such failure (other
than any failure to make any payment under the Guaranty, 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;



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     4. The maturity of any Indebtedness of the Company, Petrobras or any Material
Subsidiary in a total aggregate principal amount of U.S.$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 U.S.$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 Guaranty, 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
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



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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 Guaranty 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 Guaranty, or the Company or Petrobras shall contest the
enforceability of this Indenture, the Notes or the Guaranty or deny that it has liability
under this Indenture, the Notes or the Guaranty;




     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) Maintenance of Corporate Existence: As it applies to the Notes, Section 10.02 of
the Original Indenture shall be replaced with the following:




          “The Company will (i) maintain in effect its corporate existence and all registrations
necessary therefor except as otherwise permitted by Article VIII and (ii) take all reasonable
actions to maintain all rights, privileges, titles to property, franchises, concessions and the
like necessary or desirable in the normal conduct of its business, activities or operations;
provided, however, that this Section 10.02 shall not require the Company to maintain any such
right, privilege, title to property or franchise, if the Company’s Board of Directors shall
determine that the preservation thereof is no longer desirable in the conduct of the business of
the Company, and that the loss thereof is not disadvantageous in any material respect to the
Holders.”




          (c) 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.




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     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
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 and to finance its
planned capital expenditures.



          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 Material
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



11









 







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 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

GUARANTY




     Section 3.01. Execution. The Trustee is hereby authorized and directed to acknowledge the
Guaranty and to perform all of its duties and obligations thereunder.



     Section 3.02. Enforcement. The Trustee shall enforce the provisions of the Guaranty against
Petrobras in accordance with the terms thereof and the terms of the Indenture and Petrobras, by
execution of this Second 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 Guaranty as if
it were a party thereto.



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



     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 guaranty 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.”



     Section 3.05. Taxes; Additional Amounts. For the avoidance of doubt, the Company’s
obligations to pay any indemnity with respect to taxes, including the obligation to pay Additional



12









 







Amounts pursuant to Section 10.10 of the Original Indenture, shall extend to any payments made by
Petrobras pursuant to the Guaranty.



ARTICLE 4

MISCELLANEOUS




     Section 4.01. Effect of the Second Supplemental Indenture. This Second 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 Second Supplemental Indenture, is in all respects
ratified and confirmed, and the Original Indenture and this Second Supplemental Indenture shall be
read, taken and construed as one and the same instrument. All provisions included in this Second
Supplemental Indenture supersede any conflicting provisions included in the Original Indenture
unless not permitted by law. The provisions of this Second 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 Second Supplemental Indenture. The
Trustee accepts the trusts created by the Original Indenture, as supplemented by this Second
Supplemental Indenture, and agrees to perform the same upon the terms and conditions of the
Original Indenture, as supplemented by this Second Supplemental Indenture.



     Section 4.02. Governing Law. This Second 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 Second 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 Second Supplemental Indenture.



     Section 4.05. 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 shall represent the
same agreement.



[SIGNATURE PAGE TO FOLLOW IMMEDIATELY]




13









 





          IN WITNESS WHEREOF, the parties have caused this Second 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:	 	 








 









 








	 	 	 	 	 	 	 
	STATE OF NEW YORK

	 	 	)	 	 	 
	 

	 	 	)	 	 	ss:
	COUNTY OF QUEENS

	 	 	)	 	 	 






          On this       day of February 2009, 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 February 2009, 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.




[Notarial Seal]




	 	 	 	 	 
	 

	 	 

Notary Public
	 	 
	 

	 	COMMISSION EXPIRES	 	 






	 	 	 	 	 	 	 
	STATE OF NEW YORK

	 	 	)	 	 	 
	 

	 	 	)	 	 	ss: 
	COUNTY OF NEW YORK

	 	 	)	 	 	 






          On this       day of February 2009, 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	 	 





 









 





	 	 	 	 	 	 	 
	 	 	THE BANK OF NEW YORK MELLON, as Trustee	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name:
	 	 
	 

	 	 	 	Title:	 	 
	 
	 	 	 	 	 	 
	 	 	WITNESSES:	 	 
	 
	 	 	 	 	 	 
	 

	 	1.	 	 	 	 
	 

	 	 	 	 

Name:
	 	 
	 

	 	2.	 	 	 	 
	 

	 	 	 	 

Name:
	 	 







 









 






	 	 	 	 	 	 	 
	STATE OF NEW YORK

	 	 	)	 	 	 
	 

	 	 	)	 	 	ss: 
	COUNTY OF NEW YORK

	 	 	)	 	 	 






          On this       day of February 2009 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 Mellon, 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 February 2009, 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	 	 
	 

	 	 	 	 	 	 






 









 





Exhibit A




Form of 7.875% Global Note due 2019




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




7.875% GLOBAL NOTES DUE 2019




No.

CUSIP No.: 71645WAN1

ISIN No.: US71645WAN11

Common Code: 041298995




Principal Amount: U.S.$          

Initial Issuance Date: February 11, 2009




          This Note is one of a duly authorized issue of notes of PETROBRAS INTERNATIONAL FINANCE
COMPANY – PIFCO, an exempted company with limited liability organized under the laws of the Cayman
Islands (the “Issuer”), designated as its 7.875% Global Notes Due 2019 (the
“Notes”), issued in an initial aggregate principal amount of ONE BILLION FIVE HUNDRED
MILLION U.S. DOLLARS (U.S.$1,500,000,000) under the Second Supplemental Indenture (the “Second
Supplemental Indenture”), effective as of February 11, 2009, by and among the Issuer, The Bank
of New York Mellon (formerly known as 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 Second 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 as the Holder of record of
this Note, the principal amount specified above in U.S. dollars on March 15, 2019 (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 15 and September 15 of each
year (or if such date is not a Business Day, the next succeeding Business Day following such day),
commencing September 15, 2009 (each such date, an “Interest Payment Date”), at a rate equal
to 7.875% 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 Business Day preceding 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
U.S.$2,000 and integral multiples of U.S.$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 QUEENS

	 	 	)	 	 	 






          On this       day of February 2009, 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 February 2009, 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.




[Notarial Seal]




	 	 	 	 	 
	 

	 	 
	 	 
	 

	 	Notary Public	 	 
	 

	 	COMMISSION EXPIRES	 	 






	 	 	 	 	 	 	 
	STATE OF NEW YORK

	 	 	)	 	 	 
	 

	 	 	)	 	 	ss: 
	COUNTY OF NEW YORK

	 	 	)	 	 	 






          On this       day of February 2009, 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: February 11, 2009



	 	 	 	 	 
	 	The Bank of New York Mellon

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 Guaranty]