Document:

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                                                                   EXHIBIT 10.16

                               SECOND AMENDMENT TO

                                SUBORDINATION AND

                             INTERCREDITOR AGREEMENT

     Amendment dated as of June 29, 2001 by and among the parties whose names
appear below (this "Amendment") to a certain Intercreditor Agreement (as defined
below).  Unless otherwise defined below, capitalized terms used in this
Agreement shall have the respective meanings set forth in the Intercreditor
Agreement.

                                    RECITALS

     WHEREAS, LTHI proposes to issue, and Capital Resource Partners IV, L.P.
("CRP IV"), proposes to purchase, up to $5,000,000 principal amount of
promissory notes (the "Bridge Notes") and warrants to purchase common stock of
the Company upon the terms and conditions set forth in Exhibit A hereto; and

     WHEREAS, the Bank is willing to consent to the issuance of the Bridge Notes
on the condition that CRP IV, the Purchaser, the Borrowers and the affiliates of
the Borrowers who are parties to the Intercreditor Agreement enter into this
Amendment with the Bank in order to provide that the terms of subordination
between the Bank and the Purchaser set forth in the Intercreditor Agreement also
apply to CRP IV and the Bridge Notes; and

     NOW, THEREFORE, in consideration of the foregoing premises and the
covenants contained herein, and for other good and valuable consideration, the
receipt of which is hereby acknowledged, the parties agree as follows:

Section 11.  Definitions.

     As used in this Amendment, capitalized terms used in this Amendment shall
have the respective meanings set forth in the Intercreditor Agreement, except as
otherwise defined above and except the following capitalized terms shall have
the following respective meanings:

          "Intercreditor Agreement" means that certain Subordination and
     Intercreditor Agreement dated as of February 26, 1999, as amended by the
     First Amendment thereto dated as of June 28, 2001, by and among the Bank,
     the Original Parties and the Additional Parties.

Section 12. Amendment of Intercreditor Agreement.

            a. The definition of "Subordinate Liabilities" set forth in the
Intercreditor Agreement is hereby amended and restated in its entirety as
follows:

          ""Subordinate Liabilities" shall mean (a) all indebtedness of the
     Company to the Subordinated Creditor for principal of and interest on the
     Notes, together
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     with any prepayment fees or premiums under the Notes, (b) all indebtedness
     of LTHI to the Subordinated Creditor for principal of and interest on the
     Bridge Notes, together with any prepayment fees or premiums under the
     Bridge Notes, (c) all indebtedness of the Dutch Subsidiary to the
     Subordinated Creditor under the Dutch Guarantee, and (d) all other
     indebtedness or liabilities of the Borrowers, direct or indirect,
     contingent or noncontingent, now existing or hereafter incurred or now or
     hereafter due and owing to the Subordinated Creditor under or with respect
     to the Notes, the Dutch Guarantee or the Purchase Agreement or otherwise,
     including fees, reimbursement obligations, expenses, costs, and post-
     petition interest in bankruptcy."

            b. The definition of "Subordinated Creditor" set forth in the
Intercreditor Agreement is hereby amended and restated in its entirety as
follows:

          ""Subordinated Creditor" shall mean the Purchaser, CRP IV and any
     holder of the Subordinate Liabilities."

            c. Section 4.3 of the Intercreditor Agreement is hereby amended by
inserting after the work "Notes" and before the word "; provided," in the
twenty-first line of such section the following additional clause:

     "and (v) any regularly-scheduled payments of interest and/or principal in
     accordance with the terms of the Bridge Note, including, without
     limitation, repayment of the Bridge Note on October 31, 2001 (provided five
     (5) business days' notice is given to the Senior Lender in respect of any
     payments of principal)"

Section 13.  Miscellaneous.

     Except as amended hereby, the Subordination Agreement shall remain in full
force and effect.  This Amendment may be executed in any number of counterparts
and by different parties hereto in separate counterparts, each of which when so
executed and delivered shall be deemed an original, and all of which
counterparts taken together shall constitute one and the same instrument.

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     IN WITNESS WHEREOF, the parties hereto have executed this Agreement under
seal as of the date first above written.

                         THE BANK:

                         SILICON VALLEY BANK

                         BY:  /s/ John D. Gaziano, Jr.
                            --------------------------
                            Name:
                            Title:

                         CRP IV:

                         CAPITAL RESOURCE PARTNERS IV, L.P.,

                         BY:  CRP PARTNERS IV, L.L.C.,
                             its General Partner

                         By:   /s/ Stephen M. Jenks
                             ----------------------
                            Stephen M. Jenks, Managing Member

                         THE ORIGINAL AND ADDITIONAL PARTIES:

                         CAPITAL RESOURCE LENDERS III, L.P.,

                         BY:  CAPITAL RESOURCE PARTNERS III,
                             L.L.C., its General Partner

                         By:   /s/ Stephen M. Jenks
                             ----------------------
                            Stephen M. Jenks, Managing Member

                         LIONBRIDGE TECHNOLOGIES HOLDINGS, B.V.

                         BY:  /s/ Rory J. Cowan
                            -------------------
                              Name:  Rory J. Cowan
                              Title:  Chairman, CEO and President

                         LIONBRIDGE TECHNOLOGIES, B.V.

                         BY:  /s/ Rory J. Cowan
                              -----------------
                              Name:  Rory J. Cowan
                              Title:  Chairman, CEO and President

                                       3
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                         LIONBRIDGE TECHNOLOGIES, INC.
                         (f/k/a Lionbridge Technologies Holdings, Inc.)

                         BY:  /s/ Rory J. Cowan
                              -----------------
                              Name:  Rory J. Cowan
                              Title:  Chairman, CEO and President

                         LIONBRIDGE TECHNOLOGIES IRELAND

                         BY:  /s/ Rory J. Cowan
                              -----------------
                              Name:  Rory J. Cowan
                              Title:  Chairman, CEO and President

                         LIONBRIDGE TECHNOLOGIES CALIFORNIA, INC.

                         BY:  /s/ Rory J. Cowan
                              -----------------
                              Name:  Rory J. Cowan
                              Title:  Chairman, CEO and President

                         LIONBRIDGE AMERICA, INC.

                         (f/k/a Lionbridge Technologies, Inc.)

                         By:  /s/ Rory J. Cowan
                              -----------------
                              Name:  Rory J. Cowan
                              Title:  Chairman, CEO and President

                                       4
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                         LIONBRIDGE K.K.
                         (f/k/a Lionbridge Japan K.K.)

                         By:  /s/ Rory J. Cowan
                              -----------------
                              Name:  Rory J. Cowan
                              Title:  Chairman, CEO and President

                         JAPANESE LANGUAGE SERVICES, INC.

                         By:  /s/ Rory J. Cowan
                              -----------------
                              Name:  Rory J. Cowan
                              Title:  Chairman, CEO and President

                         LIONBRIDGE TECHNOLOGIES SARL

                         (f/k/a Lionbridge Technologies (France)

                         By:  /s/ Rory J. Cowan
                              -----------------
                              Name:  Rory J. Cowan
                              Title:  Chairman, CEO and President

                         INT'L.com, INC.

                         BY:  /s/ Rory J. Cowan
                              -----------------
                              Name:  Rory J. Cowan
                              Title:  Chairman, CEO and President

                         INTERNATIONAL LANGUAGE ENGINEERING
                           CORPORATION

                         BY:  /s/ Rory J. Cowan
                              -----------------
                              Name:  Rory J. Cowan
                              Title:  Chairman, CEO and President

                         HARVARD TRANSLATIONS, INC.

                         BY:  /s/ Rory J. Cowan
                              -----------------
                              Name:  Rory J. Cowan
                              Title:  Chairman, CEO and President

                                       5
<PAGE>

                                                                       EXHIBIT A
                                                                       ---------

                               BRIDGE NOTE TERMS
                          CAPITAL RESOURCE PARTNERS IV
                                 JUNE 26, 2001

Borrower:      Lionbridge Technologies Holdings, Inc.

Lender:        Capital Resource Partners IV (CRP IV)

Amount:        $5.0 million

Coupon:        12.0% payable quarterly

Repayment:     Due in full including all accrued and unpaid interest on
               October 31, 2001 unless previously converted.

Conversion:    Upon a Qualified Financing, the Bridge Note and all accrued but
               unpaid interest will convert to the form of the Qualified
               Financing. A Qualified Financing will be a Senior Subordinated
               Note and Warrant financing provided by Capital Resource Partners
               on the terms outlined in the Letter of Intent dated June 26,
               2001.

Warrant
Coverage:      CRP IV will receive a Common Stock Warrant for the number of
               common shares determined by dividing $1.0 million by 80.0% of the
               45 trading day trailing average closing share price on October
               31, 2001. The conversion price of the Common Stock Warrant will
               be the 45 trading day trailing average closing share price on
               October 31, 2001. However, in no case will the total shares
               represented by this Warrant exceed 900,000.

               If the Series A financing is not completed by October 31, 2001
               and the Bridge Note is not repaid, then the Bridge Note will
               convert into an $8.0 million 12.0% Senior Subordinated Note due
               September 30, 2006 which shall have no amortization prior to its
               September 30, 2006 maturity date.

Conditions:    The proceeds of the Bridge Note will be used as a deposit in
               conjunction with Lionbridge's bid to acquire Mendez S.A. and
               other corporate purposes. All other Terms and Conditions of the
               Bridge Note will be standard for a financing of this type.

                                       6<PAGE>
                                                                    Exhibit 10.1

                      FOURTH LOAN MODIFICATION AGREEMENT

     This Fourth Loan Modification Agreement (this "Loan Modification
Agreement") is entered into as of May 4, 2001, by and between CENTRA SOFTWARE,
INC., a Delaware corporation with its principal place of business at 430 Bedford
Street, Lexington, Massachusetts 02173 ("Borrower") and SILICON VALLEY BANK, a
California-chartered bank, with its principal place of business at 3003 Tasman
Drive, Santa Clara, California 95054 and with a loan production office located
at One Newton Executive Park, Suite 200, 2221 Washington Street, Newton,
Massachusetts 02462, doing business under the name "Silicon Valley East"
("Bank").

1.   DESCRIPTION OF EXISTING INDEBTEDNESS. Among other indebtedness which may be
     ------------------------------------
owing by Borrower to Bank, Borrower is indebted to Bank pursuant to a loan
arrangement dated as of November 5, 1997, evidenced by, among other documents, a
certain Loan and Security Agreement dated as of November 5, 1997, as affected
and amended by (i) a First Loan Modification Agreement dated December 30, 1998,
(ii) a Second Loan Modification Agreement dated April 12, 1999, and (iii) a
Third Loan Modification Agreement dated December 22, 2000 (the "Loan
Agreement").  Capitalized terms used but not otherwise defined herein shall have
the same meaning as in the Loan Agreement.

Hereinafter, all indebtedness and obligations owing by Borrower to Bank shall be
referred to as the "Obligations".

2.   DESCRIPTION OF COLLATERAL.  Repayment of the Obligations is secured by the
     -------------------------
Collateral as described in the Loan Agreement (together with any other
collateral security granted to Bank, the "Security Documents").

Hereinafter, the Security Documents, together with all other documents
evidencing or securing the Obligations shall be referred to as the "Existing
Loan Documents".

3.   DESCRIPTION OF CHANGE IN TERMS.
     ------------------------------

     A.   Modification(s) to Loan Agreement.

          1.   The Loan Agreement shall be amended by deleting the following
               definition appearing in Section 1.1 thereof:

                    ""2000 Committed Equipment Line" means a Credit Extension of
                    up to Two Million Dollars ($2,000,000.00)."

               and inserting in lieu thereof the following:

                    ""2000 Committed Equipment Line" means a Credit Extension of
                    up to Four Million Five Hundred Thousand Dollars
                    ($4,500,000.00)."

          2.   The Loan Agreement shall be amended by deleting Section 2.1.5(d)
               thereof and inserting in lieu thereof the following:

                    "(d) In the event the Borrower prepays in whole Equipment
                    Advances made under the 2000 Committed Equipment Line, the
                    Borrower shall be additionally obligated to the Bank for a
                    prepayment fee equal to (i) Forty-Five Thousand Dollars
                    ($45,000.00) if the 2000 Committed Equipment Line is prepaid
                    on or before December 22, 2001, and (ii) Twenty-Two Thousand
                    Five Hundred Dollars ($22,500.00) if the 2000 Committed
                    Equipment Line is prepaid after December 22, 2001 but on or
                    before December 22, 2003."

                                       1
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          3.   Notwithstanding the terms of the Loan Agreement, Bank hereby
               agrees that in connection with the initial Equipment Advance made
               by Bank (in an amount determined by Bank) on or after the date of
               this Loan Modification Agreement, invoices submitted to Bank for
               financing may have invoice dates from and after January 1, 2001.

4.   FEE. Borrower shall pay to Bank on demand all fees (including all
     ---
attorneys' fees), costs, and expenses incurred by Bank in connection with the
execution and delivery of this Loan Modification Agreement.

5.   RATIFICATION OF NEGATIVE PLEDGE.  Borrower hereby ratifies, confirms and
     -------------------------------
reaffirms, all and singular, the terms and conditions of a certain Negative
Pledge Agreement dated as of November 5, 1997 between Borrower and Bank, and
acknowledges, confirms and agrees that said Negative Pledge Agreement shall
remain in full force and effect.

6.   ADDITIONAL COVENANTS: RATIFICATION OF PERFECTION CERTIFICATE.  Borrower
     ------------------------------------------------------------
shall not, without providing the Bank with prior written notice: (i) except as
disclosed in the Perfection Certificate (defined below), relocate its principal
executive office or add any new offices or business locations or keep any
Collateral in any additional locations, or (ii) change its state of formation,
or (iii) change its organizational structure, (iv) change its legal name, or (v)
change any organizational number (if any) assigned by its state of formation.
In addition, the Borrower hereby certifies that no Collateral is in the
possession of any third party bailee (such as at a warehouse).  In the event
that Borrower, after the date hereof, intends to store or otherwise deliver the
Collateral to such a bailee, then Borrower shall receive the prior written
consent of Bank and such bailee must acknowledge in writing that the bailee is
holding such Collateral for the benefit of Bank.  Borrower hereby ratifies,
confirms and reaffirms, all and singular, the terms and disclosures contained in
a certain Perfection Certificate dated as of December 22, 2000 between Borrower
and Bank (the "Perfection Certificate"), and acknowledges, confirms and agrees
the disclosures and information above Borrower provided to Bank in the
Perfection Certificate have not changed, as of the date hereof.

7.   AUTHORIZATION TO FILE.  Borrower hereby authorizes Bank to file financing
     ---------------------
statements without notice to Borrower, with all appropriate jurisdictions, as
Bank deems appropriate, in order to further perfect or protect Bank's interest
in the Collateral.

8.   CONCERNING REVISED ARTICLE 9 OF THE UNIFORM COMMERCIAL CODE.  The Borrower
     -----------------------------------------------------------
affirms and reaffirms that notwithstanding the terms of the Security Documents
to the contrary, that the definition of "Code", "UCC" or "Uniform Commercial
Code" as set forth in the Security Documents shall be deemed to mean and refer
to "the Uniform Commercial Code as adopted by The Commonwealth of Massachusetts
(presently, Mass. Gen. Laws. Ch. 106), may be amended and in effect from time to
time.  In connection therewith, the Collateral shall include, without
limitation, the following categories of assets as defined in the Code: goods
(including inventory, equipment and any accessions thereto), instruments
(including promissory notes), documents, accounts (including health-care-
insurance receivables, and license fees), chattel paper (whether tangible or
electronic), deposit accounts, letter-of-credit rights (whether or not the
letter of credit is evidenced by a writing), commercial tort claims, securities
and all other investment property, general intangibles (including payment
intangibles and software) but excluding intellectual property, as set forth in

                                       2
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the Loan Agreement, supporting obligations and any and all proceeds of any
thereof, wherever located, whether now owned or hereafter acquired.

9.   CONSISTENT CHANGES.  The Existing Loan Documents are hereby amended
     -------------------
wherever necessary to reflect the changes described above.

10.  RATIFICATION OF LOAN DOCUMENTS.  Borrower hereby ratifies, confirms, and
     ------------------------------
reaffirms all terms and conditions of all security or other collateral granted
to the Bank, and confirms that the indebtedness secured thereby includes,
without limitation, the Obligations.

11.  NO DEFENSES OF BORROWER.  Borrower agrees that, as of this date, it has no
     -----------------------
defenses against the obligations to pay any amounts under the Obligations.

12.  CONTINUING VALIDITY.  Borrower understands and agrees that in modifying the
     -------------------
existing Obligations, Bank is relying upon Borrower's representations,
warranties, and agreements, as set forth in the Existing Loan Documents.  Except
as expressly modified pursuant to this Loan Modification Agreement, the terms of
the Existing Loan Documents remain unchanged and in full force and effect.
Bank's agreement to modifications to the existing Obligations pursuant to this
Loan Modification Agreement in no way shall obligate Bank to make any future
modifications to the Obligations.  Nothing in this Loan Modification Agreement
shall constitute a satisfaction of the Obligations.  It is the intention of Bank
and Borrower to retain as liable parties all makers of Existing Loan Documents,
unless the party is expressly released by Bank in writing.  No maker will be
released by virtue of this Loan Modification Agreement.

13.  RIGHT OF SET-OFF.  In consideration of Bank's agreement to enter into this
     ----------------
Loan Modification Agreement, Borrower and any guarantor hereby grant to Bank, a
lien, security interest and right of setoff as security for all Obligations to
Bank, whether now existing or hereafter arising upon and against all deposits,
credits, collateral and property, now or hereafter in the possession, custody,
safekeeping or control of Bank or any entity under the control of Silicon Valley
Bank or in transit to any of them.  At any time after the occurrence and during
the continuance of an Event of Default, without demand or notice, Bank may set
off the same or any part thereof and apply the same to any liability or
obligation of Borrower and any guarantor even though unmatured and regardless of
the adequacy of any other collateral securing the loan.  ANY AND ALL RIGHTS TO
REQUIRE BANK TO EXERCISE ITS RIGHTS OR REMEDIES WITH RESPECT TO ANY OTHER
COLLATERAL WHICH SECURES THE OBLIGATIONS, PRIOR TO EXERCISING ITS RIGHT OF
SETOFF WITH RESPECT TO SUCH DEPOSITS, CREDITS OR OTHER PROPERTY OF THE BORROWER
OR ANY GUARANTOR, ARE HEREBY KNOWINGLY, VOLUNTARILY AND IRREVOCABLY WAIVED.

14.  JURISDICTION/VENUE.  Borrower accepts for itself and in connection with its
     ------------------
properties, unconditionally, the non-exclusive jurisdiction of any state or
federal court of competent jurisdiction in the Commonwealth of Massachusetts in
any action, suit, or proceeding of any kind against it which arises out of or by
reason of this Loan Modification Agreement; provided, however, that if for any
reason Bank cannot avail itself of the courts of the Commonwealth of
Massachusetts, then venue shall lie in Santa Clara County, California.

15.  COUNTERSIGNATURE.  This Loan Modification Agreement shall become effective
     ----------------
only when it shall have been executed by Borrower and Bank (provided, however,
in no event shall this Loan Modification Agreement become effective until signed
by an officer of Bank in California).

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                                       3
<PAGE>

     This Loan Modification Agreement is executed as a sealed instrument under
the laws of the Commonwealth of Massachusetts as of the date first written
above.

BORROWER:                           BANK:

CENTRA SOFTWARE, INC.               SILICON VALLEY BANK, doing business as
                                    SILICON VALLEY EAST

By:                                 By:
     -----------------------------       ----------------------------------
Name:                               Name:
     -----------------------------       ----------------------------------
Title:                              Title:
     -----------------------------       ----------------------------------

                                    SILICON VALLEY BANK

                                    By:
                                         ----------------------------------
                                    Name:
                                         ----------------------------------
                                    Title:
                                         ----------------------------------
                                     (signed in Santa Clara County, California)

                                       4

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