Document:

EXHIBIT 10.1

 

TWENTy-THIRD
AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT

 

This TWENTy-THIRD
AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT (this “Amendment”) is made and entered into as of February
14, 2018 (the “Amendment Closing Date”) by and among Bacterin
International, Inc., a Nevada corporation (the “Borrower”), ROS
acquisition offshore lp, a Cayman Islands Exempted Limited Partnership (“ROS”), ORBIMED ROYALTY
OPPORTUNITIES II, LP, a Delaware limited partnership (“Royalty Opportunities”), and, in their capacity as
Guarantors under the Credit Agreement (as defined below), XTANT MEDICAL HOLDINGS, INC., a Delaware corporation (“Holdings”),
X-SPINE SYSTEMS, INC., an Ohio corporation (“X-Spine” or the “Additional Delayed Draw Borrower”
and, together with the Borrower, the “Borrowers”) and XTANT MEDICAL, INC., a Delaware corporation (“Xtant”
and, along with Holdings and X-Spine, collectively, the “Guarantors”).

 

WHEREAS, the Borrowers,
ROS and Royalty Opportunities are party to that certain Amended and Restated Credit Agreement, dated as of July 27, 2015, as amended
by that certain First Amendment to Amended and Restated Credit Agreement, dated as of March 31, 2016, that certain Second Amendment
to Amended and Restated Credit Agreement, dated as of May 25, 2016, that certain Third Amendment to Amended and Restated Credit
Agreement, dated as of June 30, 2016, that certain Fourth Amendment to Amended and Restated Credit Agreement, dated as of July
29, 2016, that certain Fifth Amendment to the Amended and Restated Credit Agreement, dated as of August 12, 2016, that certain
Sixth Amendment to the Amended and Restated Credit Agreement, dated as of September 27, 2016, that certain Seventh Amendment to
the Amended and Restated Credit Agreement, dated as of December 31, 2016, that certain Eighth Amendment to Amended and Restated
Credit Agreement, dated as of January 13, 2017, that certain Ninth Amendment to Amended and Restated Credit Agreement, dated as
of January 31, 2017, that certain Tenth Amendment to Amended and Restated Credit Agreement, dated as of February 14, 2017, that
certain Eleventh Amendment to Amended and Restated Credit Agreement, dated as of February 28, 2017, that certain Twelfth Amendment
and Waiver to Amended and Restated Credit Agreement, dated as of March 31, 2017, that certain Thirteenth Amendment to Amended and
Restated Credit Agreement, dated as of April 30, 2017, that certain Fourteenth Amendment to Amended and Restated Credit Agreement,
dated as of May 11, 2017, that certain Fifteenth Amendment to Amended and Restated Credit Agreement, dated as of June 30, 2017,
that certain Sixteenth Amendment to Amended and Restated Credit Agreement, dated as of July 15, 2017, that certain Seventeenth
Amendment and Waiver to Amended and Restated Credit Agreement, dated as of August 11, 2017, that certain Eighteenth Amendment to
Amended and Restated Credit Agreement, dated as of September 29, 2017, that certain Nineteenth Amendment to Amended and Restated
Credit Agreement, dated as of October 31, 2017, that certain Waiver, dated as of November 14, 2017, that certain Twentieth Amendment
and Waiver to Amended and Restated Credit Agreement, dated as of November 30, 2017, that certain Twenty-First Amendment to Amended
and Restated Credit Agreement, dated as of December 28, 2017 and that certain Twenty-Second Amendment to Amended and Restated Credit
Agreement, dated as of January 30, 2018 (the “Credit Agreement”), pursuant to which (i) ROS and Royalty Opportunities,
as Lenders under the Credit Agreement, have extended credit to the Borrowers on the terms set forth therein and (ii) each Lender
has appointed ROS as the administrative agent (the “Administrative Agent”) for the Lenders;

 

     

     

    

 

WHEREAS, the Guarantors
and the Administrative Agent entered into an Amended and Restated Guarantee, dated as of July 31, 2015 and supplemented on September
11, 2015, pursuant to which the Guarantors have agreed to guarantee the Obligations of the Borrowers under the Credit Agreement;

 

WHEREAS, pursuant
to Section 11.1 of the Credit Agreement, the Credit Agreement may be amended by an instrument in writing signed by each of the
Borrowers and the Administrative Agent (acting on behalf of the Lenders); and

 

WHEREAS, the Borrowers
and the Lenders desire to amend certain provisions of the Credit Agreement as provided in this Amendment.

 

NOW, THEREFORE,
in consideration of the mutual agreements herein contained, and for other good and valuable consideration, the receipt and sufficiency
of which are hereby acknowledged, the parties hereto agree as follows:

 

1.       Definitions;
Loan Document. Capitalized terms used herein without definition shall have the meanings assigned to such terms in the Credit
Agreement. This Amendment shall constitute a Loan Document for all purposes of the Credit Agreement and the other Loan Documents.

 

2.       Amendment
to Section 1.1. Section 1.1 of the Credit Agreement is hereby amended by amending and restating the following definitions
in their entirety as follows:

 

“Change in Control”
means and shall be deemed to have occurred if (i) any “person” or “group” (within the meaning of Rule 13d-5
of the Securities Exchange Act of 1934 as in effect on the date hereof) (other than OrbiMed Advisors LLC and any of its Affiliates)
shall own, directly or indirectly, beneficially or of record, determined on a fully diluted basis, more than 35% of the Voting
Securities of Holdings; (ii) a majority of the seats (other than vacant seats) on the board of directors (or equivalent) of
Holdings shall at any time be occupied by persons who were neither (x) nominated by the board of directors of Holdings nor
(y) appointed by directors so nominated; or (iii) Holdings shall cease to own, directly or indirectly, beneficially and of
record, 100% of the issued and outstanding Capital Securities of the Borrower or the Subsidiaries. The Acquisition and the transactions
contemplated by the Acquisition Agreement (including under the “Escrow Agreement,” as defined in the Acquisition Agreement)
shall not be deemed to be a “Change in Control.”

 

“Consolidated EBITDA”
shall mean, for Holdings and its Subsidiaries, for any period, an amount equal to the sum of (i) Consolidated Net Income for such
period plus (ii) solely to the extent deducted in determining Consolidated Net Income for such period, and without duplication,
(A) Consolidated Interest Expense, (B) income tax expense determined on a consolidated basis in accordance with GAAP, (C) depreciation
and amortization determined on a consolidated basis in accordance with GAAP, (D) compensation paid solely in Capital Securities
of Holdings that are not Disqualified Capital Securities, (E) non-cash impairment charges, (F) out-of-pocket fees, costs and expenses
actually paid in connection with the closing of the transactions contemplated by that certain Restructuring and Exchange Agreement,
dated as of January 11, 2018, by and among Holdings, the Lenders and the Consenting Noteholders parties thereto, (G) severance
costs or one-time reduction-in-force compensation expenses paid to employees, (H) expenses associated with the Dayton repurposing
and restructuring of the sales organization approved by the Administrative Agent in its sole discretion and (I) all other non-cash
charges approved by the Administrative Agent in its sole discretion, determined on a consolidated basis in accordance with GAAP,
in each case for such period.

 

    -2- 

     

    

 

“LIBO Rate”
means the three-month London Interbank Offered Rate for deposits in U.S. Dollars at approximately 11:00 a.m. (London, England time),
quoted by the Administrative Agent from the appropriate Bloomberg or Reuters page selected by the Administrative Agent (or any
successor thereto or similar source determined by the Administrative Agent from time to time), which shall be that three-month
London Interbank Offered Rate for deposits in U.S. Dollars in effect two Business Days prior to the last Business Day of the Fiscal
Quarter immediately prior to the relevant Fiscal Quarter, adjusted for any reserve requirement in effect on such Business Day (including,
basic, supplemental, marginal and emergency reserves) under any regulations of the Board or other Governmental Authority having
jurisdiction with respect thereto dealing with reserve requirements prescribed for eurocurrency funding (currently referred to
as "Eurocurrency Liabilities" in Regulation D of the Board) maintained by a member bank of the Federal Reserve System),
such rate to be rounded up to the nearest 1/16 of 1% and such rate to be reset quarterly as of the first Business Day of each Fiscal
Quarter. If the Loans are advanced other than on the first Business Day of a Fiscal Quarter, the initial LIBO Rate shall be that
three-month London Interbank Offered Rate for deposits in U.S. Dollars in effect two Business Days prior to the date of the Loans,
which rate shall be in effect until (and including) the last Business Day of the Fiscal Quarter next ending. The Administrative
Agent’s internal records of applicable interest rates shall be determinative in the absence of manifest error.

 

“Optional PIK Interest”
is defined in Section 3.4(a)(iii).

 

3.       Amendment
to Section 1.1. Section 1.1 of the Credit Agreement is hereby amended by deleting the definition of “Additional PIK
Interest” in its entirety.

 

4.       Amendment
to Section 3.2. Section 3.2 of the Credit Amendment is hereby amended by deleting “9.0%” from such Section
3.2 and inserting “1.0%” in replacement thereof.

 

5.       Amendments
to Section 3.4. Section 3.4 of the Credit Agreement is hereby amended and restated in its entirety as follows:

 

“SECTION
3.4 Interest Rate.

 

(a) From and
after the Restatement Date until June 30, 2016:

 

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(i)       interest
payable in cash by the Borrower shall accrue on the Loans during such period at a rate per annum equal to 9.00%;

 

(ii)       additional
interest (“PIK Interest”) shall accrue on the Loans during such period at a rate per annum equal to the difference
of (A) the sum of (1) the Applicable Margin plus (2) the higher of (x) the LIBO Rate for such Interest Period and (y) 1.00% minus
(B) 9.00%, and such PIK Interest shall be added to the outstanding principal amount of the Loans on the last day of each Fiscal
Quarter until July 1, 2016; and

 

(iii)        notwithstanding
anything in this Section 3.4(a) to the contrary, from and after the Restatement Date until March 31, 2016 , the Borrower
may elect, in its sole discretion and in lieu of interest payments pursuant to Section 3.4(a)(i) and Section 3.4(a)(ii)
during such period, by delivering written notice to the Administrative Agent prior to the date on which the first cash interest
payment would be payable pursuant to Section 3.4(a)(i) and Section 3.6(c), to have all or any portion (as the Borrower
shall so elect) of interest on the Loans accrue on the Loans during such period at a rate per annum equal to the sum of (1) the
Applicable Margin plus (2) the higher of (x) the LIBO Rate for such Interest Period and (y) 1.00% (“Optional PIK Interest”),
and such Optional PIK Interest shall be added to the outstanding principal amount of the Loans on the last day of each Fiscal Quarter
until March 31, 2016.

 

(b) From and after
July 1, 2016 until February 13, 2018, PIK Interest shall accrue on the Loans during such period at a rate per annum equal to the
difference of the sum of (1) the Applicable Margin plus (2) the higher of (x) the LIBO Rate for such Interest Period and (y) 1.00%,
and such PIK Interest shall be added to the outstanding principal amount of the Loans on the last day of each Fiscal Quarter until
December 31, 2017 and on February 14, 2018;

 

(c) From and after
February 14, 2018 until December 31, 2018:

 

(i)       interest
payable in cash by the Borrower shall accrue on the Loans during such period at a rate per annum equal to the sum of (1) 10.00%
plus (2) the LIBO Rate for such Interest Period; and

 

(ii)        notwithstanding
anything in this Section 3.4(c) to the contrary, from and after February 14, 2018 until December 31, 2018, the Borrower
may elect, in its sole discretion and in lieu of interest payments pursuant to Section 3.4(c)(i) during such period, by
delivering written notice to the Administrative Agent prior to the date on which the first cash interest payment would be payable
pursuant to Section 3.4(c)(i) and Section 3.6(c), to have all or any portion (as the Borrower shall so elect) of
interest on the Loans accrue on the Loans during such period as Optional PIK Interest at a rate per annum equal to the sum of (1)
12.00% plus (2) the LIBO Rate for such Interest Period, and such Optional PIK Interest shall be added to the outstanding principal
amount of the Loans on the last day of each Fiscal Quarter until December 31, 2018.

 

(d) From and after
January 1, 2019 until June 30, 2019:

 

(i)       interest
payable in cash by the Borrower shall accrue on the Loans during such period at a rate per annum equal to the sum of (1) 10.00%
plus (2) the LIBO Rate for such Interest Period; and

 

    -4- 

     

    

 

(ii)        notwithstanding
anything in this Section 3.4(d) to the contrary, from and after January 1, 2019 until June 30, 2019, the Borrower may elect,
in its sole discretion and in lieu of interest payments pursuant to Section 3.4(d)(i) during such period, by delivering
written notice to the Administrative Agent prior to the date on which the first cash interest payment would be payable pursuant
to Section 3.4(d)(i) and Section 3.6(c), to have all or any portion (as the Borrower shall so elect) of interest
on the Loans accrue on the Loans during such period as Optional PIK Interest at a rate per annum equal to the sum of (1) 15.00%
plus (2) the LIBO Rate for such Interest Period, and such Optional PIK Interest shall be added to the outstanding principal amount
of the Loans on the last day of each Fiscal Quarter until June 30, 2019.

 

(e) From and after
July 1, 2019 until the Maturity Date, interest payable in cash by the Borrower shall accrue on the Loans during such period at
a rate per annum equal to the sum of (1) 10.00% plus (2) the LIBO Rate for such Interest Period.

 

(f) The interest rate
shall be recalculated and, if necessary, adjusted for each Interest Period, in each case pursuant to the terms hereof.

 

(g) All references
hereunder to the principal amount of the Loans shall include any PIK Interest or Optional PIK Interest, if any, so added to the
principal.

 

(h) Notwithstanding
anything in this Section 3.4 to the contrary, the Borrower may, in its sole discretion, and in lieu of PIK Interest and/or Optional
PIK Interest payments pursuant to Sections 3.4(a), (b), (c) or (d), by delivering written notice to
the Administrative Agent prior to the date on which any such payment-in-kind interest payment would have been payable pursuant
to Section 3.4(a), (b). (c) or (d) and Section 3.6(c), elect to pay such aggregate principal
amount of PIK Interest and/or Optional PIK Interest in cash instead of making payment-in-kind, in which case the Borrower shall
be required to make such PIK Interest and/or Optional PIK Interest payment in cash at the time such payment-in-kind interest would
have been payable pursuant to Section 3.4(a), (b), (c) or (d) and Section 3.6(c).”

 

6.       Amendments
to Section 3.5. Section 3.5 of the Credit Agreement is hereby amended by deleting “, Additional PIK Interest”
from such Section 3.5.

 

7.       Amendments
to Section 3.6. Section 3.6 of the Credit Agreement is hereby amended by deleting the last sentence from such Section 3.6
in its entirety.

 

8.       Amendments
to Section 8.4(a). Section 8.4(a) of the Credit Agreement is hereby amended and restated in its entirety to read as follows:

 

“(a)        [Intentionally
Omitted.]”

 

9.       Amendments
to Section 8.4(b). Section 8.4(b) of the Credit Agreement is hereby amended by deleting the first two sentences from such
Section 8.4(b) in their entirety and inserting the following in lieu thereof:

 

“At
all times after February 14, 2018, the Liquidity shall not be less than $500,000.”

 

    -5- 

     

    

 

10.       Amendments
to Section 8.4(c). Section 8.4(c) of the Credit Agreement is hereby amended and restated in its entirety to read as follows:

 

“(c) Consolidated
Senior Leverage Ratio. The Consolidated Senior Leverage Ratio shall not be greater than the amount set forth below at any time,
in each case, other than as set forth in the definition thereof, with respect to the most recent period of four Fiscal Quarters
then ended (starting at the time that the financial statements for the most recent four Fiscal Quarters ended June 30, 2019 are
required to have been delivered hereunder (or have been so delivered, if earlier)):

 

	Four Fiscal 

Quarters Ended	Consolidated Senior

Leverage Ratio
	June 30, 2019	10.00:1.00
	September 30, 2019	10.00:1.00
	December 31, 2019	8.00:1.00
	March 31, 2020	7.00:1.00
	June 30, 2020	7.00:1.00

 

11.       Amendments
to Section 8.4(d). Section 8.4 of the Credit Amendment is hereby amended by adding the following as a new Section 8.4(d):

 

“(d) Consolidated
EBITDA. The Consolidated EBITDA for the periods set forth below shall not be less than the amounts set forth opposite such
periods for the periods set forth below:

 

	Testing Period	Minimum Consolidated EBITDA
	Three Fiscal Quarters ended September 30, 2018	$2.2 million
	Four Fiscal Quarters ended December 31, 2018	$4.0 million 
	Four Fiscal Quarters ended March 31, 2019	$5.5 million
	Four Fiscal Quarters ended June 30, 2019	$7.0 million
	Four Fiscal Quarters ended September 30, 2019	$8.5 million
	Four Fiscal Quarters ended December 31, 2019	$10.0 million
	Four Fiscal Quarters ended March 31, 2020	The greater of (a) $10.0 million or (b) 75% of projected Adjusted EBITDA for such period pursuant to projections, based on good faith estimates and assumptions believed by the Borrower to be reasonable at the time made, delivered to the Administrative Agent no later than December 31, 2019
	Four Fiscal Quarters ended June 30, 2020	The greater of (a) $10.0 million or (b) 75% of projected Adjusted EBITDA for such period pursuant to projections, based on good faith estimates and assumptions believed by the Borrower to be reasonable at the time made, delivered to the Administrative Agent no later than December 31, 2019

 

    -6- 

     

    

 

12.       Waiver.
The Lenders hereby waive any non-compliance with (a) the covenant set forth in Section 8.4(a) of the Credit Agreement as in effect
prior to this Amendment for the Fiscal Quarter ended December 31, 2017, (b) the covenant set forth in the second sentence of Section
8.4(b) of the Credit Agreement as in effect prior to this Amendment for the period from and including November 1, 2017 through
and including December 31, 2017 and (c) the covenant set forth in Section 8.4(c) of the Credit Agreement as in effect prior to
this Amendment for the four Fiscal Quarters ended December 31, 2017.

 

13.       Conditions
to Effectiveness of Amendment. This Amendment shall become effective upon receipt by the Borrowers, the Administrative
Agent, the Lenders and the Guarantors of a counterpart signature of the others to this Amendment duly executed and delivered by
each of the Borrowers, the Lenders, the Administrative Agent and the Guarantors.

 

14.       Expenses.
The Borrowers agree to pay on demand all expenses of the Administrative Agent (including, without limitation, the fees and out-of-pocket
expenses of Covington & Burling LLP, counsel to the Administrative Agent) incurred in connection with the Administrative Agent’s
review, consideration and evaluation of this Amendment, including the rights and remedies available to it in connection therewith,
and the negotiation, preparation, execution and delivery of this Amendment.

 

15.       Representations
and Warranties. The Borrowers and the Guarantors represent and warrant to each Lender as follows:

 

(a)       After
giving effect to this Amendment, the representations and warranties of the Borrowers and the Guarantors contained in the Credit
Agreement or any other Loan Document shall, (i) with respect to representations and warranties that contain a materiality qualification,
be true and correct in all respects on and as of the date hereof, and (ii) with respect to representations and warranties that
do not contain a materiality qualification, be true and correct in all material respects on and as of the date hereof, and except
that the representations and warranties limited by their terms to a specific date shall be true and correct as of such date.

 

(b)       Before
and after giving effect to this Amendment, no Default or Event of Default under the Credit Agreement has occurred or will occur
or be continuing.

 

    -7- 

     

    

 

16.       No
Implied Amendment or Waiver. Except as expressly set forth in this Amendment, this Amendment shall not, by implication
or otherwise, limit, impair, constitute a waiver of or otherwise affect any rights or remedies of the Administrative Agent or the
Lenders under the Credit Agreement or the other Loan Documents, or alter, modify, amend or in any way affect any of the terms,
obligations or covenants contained in the Credit Agreement or the other Loan Documents, all of which shall continue in full force
and effect. Nothing in this Amendment shall be construed to imply any willingness on the part of the Administrative Agent or the
Lenders to agree to or grant any similar or future amendment, consent or waiver of any of the terms and conditions of the Credit
Agreement or the other Loan Documents.

 

17.       Waiver
and Release. TO INDUCE THE ADMINISTRATIVE AGENT, ACTING ON BEHALF OF THE LENDERS, TO AGREE TO THE TERMS OF THIS AMENDMENT,
THE BORROWERS, THE GUARANTORS AND THEIR AFFILIATES (COLLECTIVELY, THE RELEASING PARTIES”) REPRESENT AND WARRANT THAT
AS OF THE DATE HEREOF THERE ARE NO CLAIMS OR OFFSETS AGAINST OR RIGHTS OF RECOUPMENT WITH RESPECT TO OR DEFENSES OR COUNTERCLAIMS
TO THEIR OBLIGATIONS UNDER THE LOAN DOCUMENTS AND IN ACCORDANCE THEREWITH THEY:

 

(a)       WAIVE
ANY AND ALL SUCH CLAIMS, OFFSETS, RIGHTS OF RECOUPMENT, DEFENSES OR COUNTERCLAIMS, WHETHER KNOWN OR UNKNOWN, ARISING PRIOR TO THE
DATE HEREOF; AND

 

(b)       FOREVER
RELEASE, RELIEVE, AND DISCHARGE THE ADMINISTRATIVE AGENT, THE LENDERS, THEIR OFFICERS, DIRECTORS, SHAREHOLDERS, MEMBERS, PARTNERS,
PREDECESSORS, SUCCESSORS, ASSIGNS, ATTORNEYS, ACCOUNTANTS, AGENTS, EMPLOYEES, AND REPRESENTATIVES (COLLECTIVELY, THE "RELEASED
PARTIES"), AND EACH OF THEM, FROM ANY AND ALL CLAIMS, LIABILITIES, DEMANDS, CAUSES OF ACTION, DEBTS, OBLIGATIONS, PROMISES,
ACTS, AGREEMENTS, AND DAMAGES, OF WHATEVER KIND OR NATURE, WHETHER KNOWN OR UNKNOWN, SUSPECTED OR UNSUSPECTED, CONTINGENT OR FIXED,
LIQUIDATED OR UNLIQUIDATED, MATURED OR UNMATURED, WHETHER AT LAW OR IN EQUITY, WHICH THE RELEASING PARTIES EVER HAD, NOW HAVE,
OR MAY, SHALL, OR CAN HEREAFTER HAVE, DIRECTLY OR INDIRECTLY ARISING OUT OF OR IN ANY WAY BASED UPON, CONNECTED WITH, OR RELATED
TO MATTERS, THINGS, ACTS, CONDUCT, AND/OR OMISSIONS AT ANY TIME FROM THE BEGINNING OF THE WORLD THROUGH AND INCLUDING THE DATE
HEREOF, INCLUDING WITHOUT LIMITATION ANY AND ALL CLAIMS AGAINST THE RELEASED PARTIES ARISING UNDER OR RELATED TO THE LOAN DOCUMENTS
OR THE TRANSACTIONS CONTEMPLATED THEREBY.

 

    -8- 

     

    

 

(c)       IN
CONNECTION WITH THE RELEASE CONTAINED HEREIN, THE RELEASING PARTIES ACKNOWLEDGE THAT THEY ARE AWARE THAT THEY MAY HEREAFTER DISCOVER
CLAIMS PRESENTLY UNKNOWN OR UNSUSPECTED, OR FACTS IN ADDITION TO OR DIFFERENT FROM THOSE WHICH THEY KNOW OR BELIEVE TO BE TRUE,
WITH RESPECT TO THE MATTERS RELEASED HEREIN. NEVERTHELESS, IT IS THE INTENTION OF THE RELEASING PARTIES, THROUGH THIS AGREEMENT
AND WITH ADVICE OF COUNSEL, FULLY, FINALLY, AND FOREVER TO RELEASE ALL SUCH MATTERS, AND ALL CLAIMS RELATED THERETO, WHICH DO NOW
EXIST, OR HERETOFORE HAVE EXISTED. IN FURTHERANCE OF SUCH INTENTION, THE RELEASES HEREIN GIVEN SHALL BE AND REMAIN IN EFFECT AS
A FULL AND COMPLETE RELEASE OR WITHDRAWAL OF SUCH MATTERS NOTWITHSTANDING THE DISCOVERY OR EXISTENCE OF ANY SUCH ADDITIONAL OR
DIFFERENT CLAIMS OR FACTS RELATED THERETO.

 

(d)       THE
RELEASING PARTIES COVENANT AND AGREE NOT TO BRING ANY CLAIM, ACTION, SUIT, OR PROCEEDING AGAINST THE RELEASED PARTIES, DIRECTLY
OR INDIRECTLY, REGARDING OR RELATED IN ANY MANNER TO THE MATTERS RELEASED HEREBY, AND FURTHER COVENANT AND AGREE THAT THIS AGREEMENT
IS A BAR TO ANY SUCH CLAIM, ACTION, SUIT, OR PROCEEDING.

 

(e)       THE
RELEASING PARTIES REPRESENT AND WARRANT TO THE RELEASED PARTIES THAT THEY HAVE NOT HERETOFORE ASSIGNED OR TRANSFERRED, OR PURPORTED
TO ASSIGN OR TRANSFER, TO ANY PERSON OR ENTITY ANY CLAIMS OR OTHER MATTERS HEREIN RELEASED.

 

18.       Counterparts;
Governing Law. This Amendment may be executed in any number of counterparts and by different parties hereto on separate
counterparts, each of such when so executed and delivered shall be an original, but all of such counterparts shall together constitute
but one and the same agreement. Delivery of an executed counterpart of a signature page of this Amendment by fax transmission or
other electronic mail transmission (e.g., “pdf” or “tif”) shall be effective as delivery of a manually
executed counterpart of this Amendment. THIS AMENDMENT SHALL BE GOVERNED BY, AND CONSTRUED IN ACCORDANCE WITH, THE INTERNAL LAWS
OF THE STATE OF NEW YORK (INCLUDING FOR SUCH PURPOSE SECTIONS 5-1401 AND 5-1402 OF THE GENERAL OBLIGATIONS LAW OF THE STATE OF
NEW YORK).

 

[Remainder
of Page Intentionally Left Blank]

 

    -9- 

     

    

 

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

 

	 	BACTERIN INTERNATIONAL, INC.,

as the Borrower

	 	 	 
	 	By:	/s/ Carl D. O’Connell
	 	Name:	Carl D. O’Connell
	 	Title:	Chief Executive Officer
	 	 	 
	 	XTANT MEDICAL HOLDINGS, INC.,
	 	(fka: Bacterin International Holdings, Inc.)
	 	as a Guarantor
	 	 	 
	 	By:	/s/ Carl D. O’Connell
	 	Name:	Carl D. O’Connell
	 	Title:	Chief Executive Officer
	 	 	 
	 	X-SPINE SYSTEMS, INC.,
	 	as a Guarantor and the Additional Delayed Draw Borrower
	 	 	 
	 	By:	/s/ Carl D. O’Connell
	 	Name:	Carl D. O’Connell
	 	Title:	Chief Executive Officer
	 	 	 
	 	XTANT MEDICAL, INC.,
	 	as a Guarantor
	 	 	 
	 	By:	/s/ Carl D. O’Connell
	 	Name:	Carl D. O’Connell
	 	Title:	Chief Executive Officer

 

Signature Page to Twenty-Third Amendment
to A&R Credit Agreement

 

     

     

    

 

	 	ROS Acquisition Offshore LP,
 as a Lender and as the Administrative Agent
	 	 	 
	 	By OrbiMed Advisors LLC, solely in its capacity as
	 	 Investment Manager
	 	 	 
	 	By:	/s/ W. Carter Neild
	 	Name:	W. Carter Neild
	 	Title:	Member
	 	 	 
	 	ORBIMED ROYALTY OPPORTUNITIES II, LP,
 as a Lender
	 	 	 
	 	By OrbiMed ROF II LLC,
	 	its General Partner
	 	By OrbiMed Advisors LLC,
	 	its Managing Member
	 	 	 
	 	By:	/s/ W. Carter Neild
	 	Name:	W. Carter Neild
	 	Title:	Member

 

Signature Page to Twenty-Third Amendment
to A&R Credit AgreementEXHIBIT 10.2

 

SECURITIES
PURCHASE AGREEMENT

 

Xtant Medical Holdings, Inc.

664 Cruiser Lane

Belgrade, Montana 59714

 

Ladies and Gentlemen:

 

Each of the undersigned (each, an “Investor”)
hereby confirms its agreement with you as follows:

 

		1.	This Securities Purchase Agreement (the “Agreement”) is made as of the Effective
Date between Xtant Medical Holdings, Inc., a Delaware corporation (the “Company”), and the Investors listed
on the signature pages hereto. 

 

		2.	The Company is proposing to issue and sell to the Investors (the “Placement”) an aggregate of $6,809,896.80
of the Company’s common stock, par value $0.000001 per share (the “Securities”),
at a price per share of $7.20 pursuant to the Restructuring and Exchange Agreement, dated as of January 11, 2018, among the Company,
the Investors and the consenting noteholders party thereto (the “Restructuring Agreement”). The Securities
will be entitled to the benefits of a Registration Rights Agreement (the “Registration Rights Agreement”), to be entered
into among the Company and the Investors, pursuant to which the Company agrees, among other thing, to file and cause to become
effective under the Securities Act of 1933, as amended (the “Securities Act”), a registration statement covering the
resale of the Securities. 

 

		3.	The Company and the Investors agree that, upon the terms and subject to the conditions set forth
herein and in the Restructuring Agreement, the Investors will purchase from the Company and the Company will issue and sell to
the Investors the number of Securities set forth below on each Investor’s signature page for the aggregate purchase price
set forth below on such Investor’s signature page. The Securities shall be purchased pursuant to the Terms and Conditions
for Purchase of Securities attached hereto as Annex A and incorporated herein by reference as if fully set forth herein.
The Securities purchased by the Investors will be delivered by electronic book-entry through the facilities of the Depository Trust
Company (“DTC”) pursuant to the Investors’ instructions at the Closing.

 

     

     

    

 

Number of Securities the Investor Agrees to Purchase: 603,687
shares

 

Aggregate Purchase Price of such Securities : $4,346,546.40

 

Please confirm that the foregoing correctly
sets forth the agreement between us by signing in the space provided below for that purpose.

 

	AGREED AND ACCEPTED BY:	 
	 	 
	______________________________________

 

	Xtant Medical Holdings, Inc.	 	Name of Investor:
	a Delaware corporation	 	ROS Acquisition Offshore LP
	 	 	 
	 	 	By OrbiMed Advisors LLC, solely in its
	 	 	capacity as Investment Manager
	 	 	 
	By: 	/s/ Carl D. O’Connell	 	By:	/s/ W. Carter Neild
	Name: Carl D. O’Connell	 	Name: W. Carter Neild
	Title: Chief Executive Officer	 	Title: Member
	 	 	 
	 	 	Address: 601 Lexington Avenue, 54th Floor
	 	New York, NY 10022
	 	 

 

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If you are a registered investment company, please provide information
relating to your Custodial Agent.

 

	 	Name of Custodial Agent: Merrill Lynch
	 	Address: 600 California St., Floor 8
	 	San Francisco, CA 94108
	 	Tax ID No.:
	 	Settlement Contact Name: Peter Miller

 

 

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Number of Securities the Investor
Agrees to Purchase: 342,132 shares

 

Aggregate Purchase Price of such
Securities : $2,463,350.40

 

Please confirm that the foregoing correctly
sets forth the agreement between us by signing in the space provided below for that purpose.

 

	AGREED AND ACCEPTED BY:	 
	 	 
	______________________________________
	 

 

	Xtant Medical Holdings, Inc.	 	Name of Investor:
	a Delaware corporation	 	OrbiMed Royalty Opportunities II, LP
	 	 	 
	 	 	By OrbiMed ROF II LLC,
	 	 	its General Partner
	 	 	 
	 	 	By OrbiMed Advisors LLC,
	 	 	its Managing Member
	 	 	 
	By: 	/s/ Carl D. O’Connell	 	By:	/s/ W. Carter Neild
	Name: Carl D. O’Connell	 	Name: W. Carter Neild
	Title: Chief Executive Officer	 	Title: Member
	 	 	 
	 	 	Address: 601 Lexington Avenue, 54th Floor
	 	New York, NY 10022
	 	 

 

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If you are a registered investment company, please provide information
relating to your Custodial Agent.

 

	 	Name of Custodial Agent: Merrill Lynch
	 	Address: 600 California St., Floor 8
	 	San Francisco, CA 94108
	 	Tax ID No.:
	 	Settlement Contact Name: Peter Miller

 

 

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ANNEX A
TO THE SECURITIES PURCHASE AGREEMENT

TERMS AND CONDITIONS FOR PURCHASE OF SECURITIES

 

		1.	Agreement to Sell and Purchase the Securities; Closings and Delivery of Securities and Funds.

 

		1.1	Upon the terms and subject to the conditions hereinafter set forth, at the Closing (as defined below), the Company will sell
to the Investors, and the Investors will purchase from the Company, the amount of Securities set forth on each such Investor’s
signature page hereto at the purchase price set forth on such signature page.

 

		1.2	The completion of the purchase and sale of the Securities (the “Closing”) shall occur on or around February
14, 2018 (the “Closing Date”), at the offices of the Company’s counsel. At the Closing, (i) the Company
shall cause the Company’s transfer agent to deliver to the Investors the Securities to the DTC account specified by the Investors
and agreed by the Company, and (ii) the aggregate purchase price for the Securities shall be delivered by or on behalf of the Investors
to the Company in the manner set forth in the funds flow memorandum attached hereto as Annex B.

 

		1.3	The Company’s obligation to issue and sell Securities to any Investor shall be subject to the accuracy of the representations
and warranties made by the Investors.

 

		1.4	The Investors’ obligation to accept delivery of the Securities and to pay for the Securities shall be subject to the
following conditions: (a) each of the representations and warranties of the Company made in Article 3 of the Restructuring Agreement
shall be accurate in all material respects as of the Closing Date; (b) the Tier 2 Transaction and Reverse Stock Split (each as
described in the Company’s definitive proxy statement filed with the SEC on January 22, 2018) shall have occurred and (c)
the Company shall have furnished to the Investors such further certificates and documents as the Investors may reasonably request.

 

		2.	Representations, Warranties and Covenants of the Company.

 

The Company hereby represents and warrants
to, and covenants with, the Investors that:

 

		2.1	The Company has full right, power, authority and capacity to enter into this Agreement and the Registration Rights Agreement
and to consummate the transactions contemplated hereby and thereby, and has taken all necessary action to authorize the execution,
delivery and performance of this Agreement and the Registration Rights Agreement.

 

		2.2	The Company has all requisite corporate power and authority to issue and sell the Securities. The Securities have been duly
authorized by the Company, and are validly issued, fully paid and non-assessable, and the Securities are not subject to any preemptive
or similar rights.

 

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		2.3	The Company hereby makes to the Investors the representations and warranties made by the Company pursuant to Article 3 of the
Restructuring Agreement as of the date hereof.

 

		3.	Representations, Warranties and Covenants of the Investors.

 

The Investors hereby represent and warrant
to, and covenant with, the Company that:

 

		3.1	(1)	 Each Investor is (a) either a QIB as defined in Rule 144A under the Securities Act, or an institutional accredited
investor as defined in Rule 501(a)(1), (a)(2), (a)(3), or (a)(7) under the Securities Act, as presently in effect, (b) aware that
the sale to it is being made in reliance on a private placement exemption from registration under the Securities Act, and (c) acquiring
the Securities for its own account or for the account of a QIB or an institutional accredited investor.

 

		(2)	Each Investor understands and agrees on behalf of itself and on behalf of any investor account for which it is purchasing the
Securities, that the Securities are being offered in a transaction not involving any public offering within the meaning of the
Securities Act, that the Securities have not been, and will not be, registered under the Securities Act and that (a) if it decides
to offer, resell, pledge or otherwise transfer any of the Securities, such Securities may be offered, resold, pledged or otherwise
transferred only (i) pursuant to an exemption from the registration requirements of the Securities Act, including Rule 144 under
the Securities Act (if available), (ii) pursuant to an effective registration statement under the Securities Act, or (iii) to the
Company, or one of its subsidiaries, in each of cases (i) through (iii) in accordance with any applicable securities laws of any
state of the United States.

 

		(3)	The Investors understand that the Securities will, unless sold pursuant to a registration statement that has been declared
effective under the Securities Act or in compliance with Rule 144, and will bear a legend that reflects the restricted nature of
the securities.

 

		(4)	Each Investor:

 

		(a)	is able to fend for itself in the transactions contemplated hereby;

 

		(b)	has such knowledge and experience in financial and business matters as to be capable of evaluating the merits and risks of
its prospective investment in the Securities; and

 

		(c)	has the ability to bear the economic risks of its prospective investment and can afford the complete loss of such investment.

 

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		(5)	Each Investor acknowledges that (a) it has conducted its own investigation of the Company, (b) it has had access to, and has
had an adequate opportunity to review, (i) all information the Company has filed with and furnished to the Securities and Exchange
Commission (the “Commission”), (ii) all information set forth in such filings, and (iii) such financial and
other information as it deems necessary to make its decision to purchase the Securities, and (c) it has been offered the opportunity
to ask questions of the Company, and received such answers thereto, as it deemed necessary in connection with the decision to purchase
the Securities.

 

		(6)	The Investors understand that the Company, and others will rely upon the truth and accuracy of the foregoing representations,
acknowledgements and agreements and agrees that if any of the representations and acknowledgements deemed to have been made by
it by its purchase of the Securities are no longer accurate, the Investors shall promptly notify the Company. If the Investors
are acquiring the Securities as a fiduciary or agent for one or more investor accounts, it represents that it has sole investment
discretion with respect to each such account and it has full power to make the foregoing representations, acknowledgements and
agreements on behalf of such account.

 

		3.2	The Investors acknowledge that no action has been or will be taken in any jurisdiction outside the United States by the Company
that would permit an offering of the Securities, or possession or distribution of offering materials in connection with the issue
of the Securities (including any filing of a registration statement), in any jurisdiction outside the United States where action
for that purpose is required. Each Investor outside the United States will comply with all applicable laws and regulations in each
foreign jurisdiction in which it purchases, offers, sells or delivers Securities or has in its possession or distributes any offering
material, in all cases at its own expense.

 

		3.3	The Investors have full right, power, authority and capacity to enter into this Agreement and to consummate the transactions
contemplated hereby and has taken all necessary action to authorize the execution, delivery and performance of this Agreement,
and this Agreement constitutes a valid, binding and enforceable obligation of the Investors, except as the enforceability of the
Agreement may be subject to or limited by bankruptcy, insolvency, reorganization, arrangement, moratorium or other similar laws
relating to or affecting the rights of creditors generally.

 

		3.4	The entry into and performance of this Agreement by the Investors and the consummation by the Investors of the transactions
contemplated hereby and thereby will not (i) result in a violation of the organizational documents of Investors, (ii) conflict
with, or constitute a default under, or give to others any rights of termination, amendment, acceleration or cancellation of any
agreement, indenture or instrument to which the Investors are party, or (iii) result in the violation of any law, rule, regulation,
order, judgment or decree (including federal and state securities laws) applicable to the Investors, except in the case of clauses
(ii) and (iii) above, for such conflicts, defaults, rights or violations which would not, individually or in the aggregate, reasonably
be expected to have a material adverse effect on the ability of the Investors to perform their obligations hereunder.

 

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		4.	Survival of Representations, Warranties and Agreements. Notwithstanding any investigation made by any party to
this Agreement, all covenants, agreements, representations and warranties made by the Company and the Investors herein shall survive
the execution of this Agreement, the delivery to the Investors of the Securities being purchased and the payment therefor.

 

		5.	Notices. All notices, requests, consents and other communications hereunder shall be in writing, shall be delivered
(A) if within the domestic United States, by first-class registered or certified mail, or nationally recognized overnight express
courier, postage prepaid, or by facsimile, or (B) otherwise by International Federal Express or facsimile, and shall be deemed
given (i) if delivered by first-class registered or certified mail, three business days after so mailed, (ii) if delivered by a
nationally recognized overnight carrier, one business day after so mailed, (iii) if delivered by International Federal Express,
two business days after so mailed and (iv) if delivered by facsimile, upon electronic confirmation of receipt and shall be delivered
as addressed as follows:

 

(a) if to the Company, to:

 

Xtant Medical Holdings, Inc.

664 Cruiser Lane

Belgrade, Montana 59714

Attention: Carl O’Connell

 

(b) if to an Investor, at its address on the signature
page hereto, or at such other address or addresses as may have been furnished to the Company in writing.

 

		6.	Independent Nature of Investors’ Obligations and Rights. The obligations of the Investors under this Agreement
are several and not joint, and no Investor shall be responsible in any way for the performance of the obligations of any other
Investor under the Agreement. The decision of each Investor to purchase the Securities pursuant to the Agreement has been made
by such Investor independently of any other Investor. Nothing contained in the Agreement, and no action taken by any Investor pursuant
thereto, shall be deemed to constitute the Investors as a partnership, an association, a joint venture or any other kind of entity,
or create a presumption that the Investors are in any way acting in concert or as a group with respect to such obligations or with
respect to the acquisition, disposition or voting of the Securities or the transactions contemplated by the Agreement. Each Investor
acknowledges that no other Investor has acted as agent for such Investor in connection with making its investment hereunder and
that no Investor will be acting as agent of such Investor in connection with monitoring its investment in the Securities or enforcing
its rights under this Agreement. Each Investor shall be entitled to independently protect and enforce its rights, including without
limitation the rights arising out of this Agreement, and it shall not be necessary for any other Investor to be joined as an additional
party in any proceeding for such purpose. No consideration shall be offered or paid to any person to amend or consent to a waiver
or modification of any provision of the Agreement unless the same consideration is also offered to all of the parties to the Agreement.

 

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		7.	Changes. Except as contemplated herein, this Agreement may not be modified or amended except pursuant to an instrument
in writing signed by the Company.

 

		8.	Headings. The headings of the various sections of this Agreement have been inserted for convenience or reference
only and shall not be deemed to be part of this Agreement.

 

		9.	Severability. In case any provision contained in this Agreement should be invalid, illegal or unenforceable in
any respect, the validity, legality and enforceability of the remaining provisions contained herein shall not in any way be affected
or impaired thereby.

 

		10.	Applicable Law; Venue. This Agreement will be governed by and construed in accordance with the laws of the State
of New York applicable to contracts made and to be performed within the State of New York. Each of the Company and the Investors
agree that any suit, action or proceeding arising out of or based upon this Agreement or the transactions contemplated hereby may
be instituted only in any State or U.S. federal court in The City of New York and County of New York and waives any objection
that such party may now or hereafter have to the laying of venue of any such suit, action or proceeding, and irrevocably submits
to the exclusive jurisdiction of such courts in any such suit, action or proceeding.

 

		11.	Waiver of Jury Trial. Each of the Company and the Investors hereby irrevocably waive, to the fullest extent permitted
by applicable law, any and all right to trial by jury in any legal proceeding arising out of or relating to this Agreement or the
transactions contemplated hereby.

 

Counterparts. This Agreement
may be signed in one or more counterparts, each of which shall constitute an original and all of which together shall constitute
one and the same agreement

 

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