TherapeuticsMD, Inc. 10-Q


Exhibit 10.5 


 





Execution
Version


 







SUBSCRIPTION
AGREEMENT


 


This
Subscription Agreement is entered into and dated as of August 5, 2020 (this “Agreement”), by and among TherapeuticsMD,
Inc., a Nevada corporation with offices located at 951 Yamato Road, Suite 220, Boca Raton, FL 33431 (the “Company”),
and the Subscribers identified on the Schedule of Subscribers attached hereto (each, a “Subscriber” and,
together, the “Subscribers”). Capitalized terms not defined below shall have the meaning as set forth in Section
1.1.


 


RECITALS


 


A.       The
Company and each Subscriber is executing and delivering this Agreement in reliance upon the exemption from securities registration
afforded by Section 4(a)(2) of the Securities Act of 1933, as amended (the “1933 Act”), and Rule 506 of Regulation
D (“Regulation D”) as promulgated by the United States Securities and Exchange Commission (the “Commission”)
under the 1933 Act.


 


B.       The
Company is a borrower under that certain Financing Agreement, dated as of April 24, 2019, by and among the Company, as borrower,
certain subsidiaries of the Company, as guarantors, the lenders from time to time party thereto, and Sixth Street Specialty Lending,
Inc. (f/k/a TPG Specialty Lending, Inc.), as administrative agent for the lenders thereunder (as amended, amended and restated,
supplemented or otherwise modified from time to time, the “Financing Agreement”).


 


C.       To
induce the Subscribers (or Affiliates thereof) to further amend the Financing Agreement, the Company wishes to issue, upon the
terms and conditions stated in this Agreement, a warrant to acquire up to that aggregate number of shares of Common Stock set
forth opposite such Subscriber’s name in column (3) on the Schedule of Subscribers, in the form attached hereto as Exhibit
A (the “Warrants”) (as exercised, collectively, the “Warrant Shares”), subject to adjustment
for any stock split, stock dividend, stock combination, reclassification or similar transaction.


 


E.       The
Warrants and the Warrant Shares are collectively referred to herein as the “Securities.”


 


NOW,
THEREFORE, IN CONSIDERATION of the mutual covenants contained in this Agreement, and for other good and valuable consideration,
the receipt and adequacy of which are hereby acknowledged, the Company and each Subscriber, severally and not jointly, agree as
follows:


 






     


     


    

 


ARTICLE
I.

DEFINITIONS


 


1.1          Definitions. In addition to the terms defined elsewhere in this Agreement, the following terms shall have the meanings
set forth in this Section 1.1:


 


“1934
Act” means the Securities Exchange Act of 1934, as amended, and the rules and regulations promulgated thereunder.


 


“Affiliate”
shall have the meaning ascribed to such term in Rule 405 of the 1933 Act.


 


“Business
Day” means any day other than Saturday, Sunday or other day on which commercial banks in the City of New York, New York
are authorized or required by law to remain closed; provided, however, for clarification, commercial banks shall
not be deemed to be authorized or required by law to remain closed due to “stay at home”, “shelter-in-place”,
“non-essential employee” or any other similar orders or restrictions or the closure of any physical branch locations
at the direction of any governmental authority so long as the electronic funds transfer systems (including for wire transfers)
of commercial banks in the City of New York, New York generally are open for use by customers on such day.


 


“Common
Stock” means (a) the Company’s shares of common stock, par value $0.001 per share, and (b) any share capital into which
such common stock shall have been changed or any share capital resulting from a reclassification, reorganization or recapitalization
of such common stock.


 


“Designee”
means Sixth Street Specialty Lending, Inc.


 


“Eligible
Market” means the Principal Market, the NYSE American, The Nasdaq Global Select Market, The Nasdaq Global Market, The
Nasdaq Capital Market or The New York Stock Exchange, Inc.


 


“Governmental
Authority” shall mean any: (a) nation, state, commonwealth, province, territory, county, municipality, district or other
jurisdiction of any nature; (b) federal, state, provincial, local, municipal, foreign or other government; (c) governmental or
quasi-governmental authority of any nature (including any governmental division, department, agency, commission, commissioner,
bureau, tribunal, instrumentality, official, ministry, fund, foundation, center, organization, board, unit, body or Person and
any court or other tribunal); or (d) regulatory or self-regulatory organization (including the Principal Market or other
applicable Eligible Market).


 


“Lien”
means any mortgage, deed of trust, lien, charge, claim, encumbrance, security interest, right of first refusal, preemptive right
or other restrictions of any kind.


 


“Person”
means an individual or corporation, partnership, trust, incorporated or unincorporated association, joint venture, limited liability
company, joint stock company, government (or an agency or subdivision thereof) or other entity of any kind.


 






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“Principal
Market” means The Nasdaq Stock Market LLC.


 


“Proceeding”
means an action, claim, suit, inquiry, investigation or proceeding (including, without limitation, an investigation or partial
proceeding, such as a deposition), whether commenced or, to the Company’s knowledge, threatened in writing.


 


“Required
Holders” means the holders of Warrants representing at least a majority of the number of shares of Common Stock issuable
upon exercise of the Warrants then outstanding and shall include the Designee so long as the Designee or any of its Affiliates
holds any Warrants.


 


“SEC
Reports” shall mean all reports, schedules, forms, applications and other documents, together with any amendments required
to be made with respect thereto, required to be filed by the Company under the 1933 Act and the 1934 Act, including pursuant to
Section 13(a) or 15(d) thereof, for the two (2) years preceding the date hereof (or such shorter period as the Company was
required by law or regulation to file such materials).


 


“Subsidiary”
has the meaning as set forth in the Financing Agreement.


 


“Trading
Day” means any day on which the Common Stock is traded on the Principal Market, or, if the Principal Market is not the
principal trading market for the Common Stock, then on the principal securities exchange or securities market on which the Common
Stock is then traded.


 


“Transaction
Documents” means this Agreement, the Warrants and any other documents, certificates, letters of instruction, or agreements
executed or delivered in connection with the transactions contemplated hereby, but shall not include the Loan Documents (as defined
in the Financing Agreement).


 


ARTICLE
II.

PURCHASE AND SALE


 


2.1         Purchase and Sale of the Securities. Subject to the terms and conditions of this Agreement, each Subscriber agrees, severally
and not jointly, to purchase from the Company, and the Company agrees to sell and issue to each Subscriber, at the Closing, such
Warrants to acquire up to that aggregate number of Warrant Shares as is set forth opposite such Subscriber’s name in column (3)
on the Schedule of Subscribers.


 


2.2         Closing. The issuance of the Warrants pursuant to the terms of this Agreement (the “Closing”) shall take
place remotely by electronic transfer of Closing documentation at 10:00 a.m. (New York City time) on the date hereof (the “Closing
Date”).


 


2.3         Form of Payment. On the Closing Date, the Company shall deliver to each Subscriber a Warrant pursuant to which such Subscriber
shall have the right to acquire up to such aggregate number of Warrant Shares as is set forth opposite such Subscriber’s name
in column (3) of the Schedule of Subscribers, duly executed on behalf of the Company and registered in the name of such
Subscriber or its designee.


 






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2.4         Tax Matters. The parties agree that for U.S. federal income tax purposes (a) pursuant to Treasury Regulation 1.761-3
the Warrant shall not be treated as stock of the Company unless and until exercised in accordance with the terms hereof, (b) the
issuance of the Warrant shall be treated as a payment in respect of the Initial Term Loan (as defined in the Financing Agreement)
(and not as a fee or as a payment of interest) and (c) (1) the Initial Term Loan and the Warrant constitute an “investment
unit” and (2) the issue price of the Initial Term Loan is $192,500,000 and the issue price of the Warrant is $7,500,000 (clauses
(a) through (b), the “Tax Treatment”). Neither the Company nor the Subscribers shall take any position inconsistent
with the Tax Treatment on any tax return except required otherwise by a change in law or pursuant to a final determination by
an applicable tax authority. 


 


ARTICLE
III.

REPRESENTATIONS AND WARRANTIES


 


3.1         Representations and Warranties of the Company. The Company hereby represents and warrants as of the date hereof and as
of the Closing Date (except for representations and warranties that speak as of a specific date, which shall be made as of such
date) to each of the Subscribers, except as set forth in the Schedules delivered herewith:


 


(a)             
Authorization; Enforcement. The Company has the requisite corporate power and authority to enter into and to consummate
the transactions contemplated by each of the Transaction Documents and otherwise to carry out its respective obligations hereunder
and thereunder. Other than the Required Approvals (as defined in Section 3.1(c)), the execution and delivery by the Company
of each of the Transaction Documents to which it is a party and the consummation by it of the transactions contemplated hereunder
and thereunder have been duly authorized by all necessary action on the part of the Company and no further consent or action is
required by the Company, or its board of directors or stockholders. Each Transaction Document has been (or upon delivery will
have been) duly executed by the Company, and, when delivered in accordance with the terms hereof, will constitute the valid and
binding obligation of the Company, enforceable against the Company, in accordance with its terms, except as such enforceability
may be limited by general principles of equity or applicable bankruptcy, insolvency, reorganization, moratorium, liquidation or
similar laws relating to, or affecting generally, the enforcement of applicable creditors’ rights and remedies and except as rights
to indemnification and to contribution may be limited by federal or state securities law.


 


(b)             
No Conflicts. The execution, delivery and performance of the Transaction Documents by the Company and the consummation
by the Company of the transactions contemplated hereby and thereby (including, without limitation, the issuance of the Warrants
and the Warrant Shares and the reservation for issuance of the Warrant Shares) do not and will not (i) conflict with or violate
any provision of the Company’s or any of its Subsidiaries’ certificate or articles of incorporation, bylaws or other organizational
or charter documents, (ii) conflict with, or constitute a default (or an event that with notice or lapse of time or both
would become a default) under, result in the creation of any Lien upon any of the properties or assets of the Company or any of
its Subsidiaries, or give to others any rights of termination, amendment, acceleration or cancellation (with or without notice,
lapse of time or both) of, any agreement, credit facility, debt or other instrument (evidencing a Company or a Company Subsidiary’s
debt or otherwise) or other understanding to which the Company any of its Subsidiaries is a party or by which any property or
asset of the Company or any of its Subsidiaries is bound or affected, or (iii) result in a violation of any law, rule, regulation,
order, judgment, injunction, decree or other restriction of any Governmental Authority to which the Company or a Company Subsidiary
is subject (including, without limitation, foreign, federal and state securities laws and regulations and the rules and regulations
of the Principal Market), or by which any property or asset of the Company or a Company Subsidiary is bound or affected; except
in the case of clause (ii) or (iii) above, as would not, reasonably be expected to, (i) have or result in a material adverse
effect on the legality, validity, binding effect or enforceability of any Transaction Document, (ii) have or result in a
material adverse effect on the business operations, properties, assets, condition (financial or otherwise) or liabilities of the
Company and its Subsidiaries, taken as a whole, or (iii) have or result in a material adverse effect on the Company’s authority
or ability to perform fully on a timely basis its obligations under any Transaction Document (any of (i), (ii) or (iii), a “Material
Adverse Effect”).


 






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(c)             
Filings, Consents and Approvals. Neither the Company nor any Company Subsidiary is required to obtain any consent, waiver,
authorization, permit or order of, give any notice to, or make any filing or registration with, any Governmental Authority or
other Person in connection with the execution, delivery and performance by the Company of the Transaction Documents, other than
(i) the filing by the Company of a Notice of Sale of Securities on Form D with the Commission under Regulation D and state and
applicable Blue Sky filings, (ii) the filing of any requisite notices and/or applications(s) to the Principal Market for the issuance
and sale of the Warrants and the issuance of the Warrant Shares upon exercise of the Warrants and the listing of the Warrant Shares
for trading thereon, and (iii) the filing of a Current Report on Form 8-K, or the disclosure required thereby in another filing,
with the Commission (collectively, but excluding the foregoing clauses (i) through (iii), the “Required Approvals”).
All Required Approvals have been obtained or effected on or prior to the Closing Date, and neither the Company nor any Company
Subsidiary are aware of any facts or circumstances which might prevent the Company or any Company Subsidiary from obtaining or
effecting any of the registration, application or filings contemplated by the Transaction Documents. The Company is not in violation
of any material requirements of the Principal Market and has no knowledge of any facts or circumstances which would reasonably
be expected to result in the delisting or suspension of the Common Stock in the foreseeable future.


 


(d)             
Issuance of the Securities. The issuance of the Warrants is duly authorized and, upon issuance in accordance with the terms
of the Transaction Documents, the Warrants will be validly issued free from all preemptive or similar rights, taxes, Liens (other
than Liens under the 1933 Act and applicable Blue Sky laws) and charges with respect to the issue thereof. As of the Closing,
the Company shall have reserved from its duly authorized capital stock not less than 100% of the maximum number of Warrant Shares
issuable upon exercise of the Warrants (without taking into account any limitations on the exercise of the Warrants set forth
therein). Upon exercise in accordance with the Warrants, the Warrant Shares when issued, will be validly issued, fully paid and
nonassessable and free from all preemptive or similar rights, taxes, Liens and charges with respect to the issue thereof, with
the holders being entitled to all rights accorded to a holder of Common Stock (as set forth in the applicable charter documents).
Subject to the accuracy of the representations and warranties of the Subscribers in this Agreement, the offer and issuance by
the Company of the Securities is exempt from registration under the 1933 Act.


 






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(e)             
Capitalization. The number of shares and type of all authorized, issued and outstanding capital stock of the Company has
been set forth in the SEC Reports and has changed since the date set forth in the most recent applicable SEC Report only to reflect
exercises of stock options and other convertible securities that have not been required to be reported by the Company under the
1934 Act. Without limiting the foregoing, as of the date hereof, immediately prior to the issuance of the Warrants, the authorized
capital stock of the Company consists of (i) 600,000,000 shares of Common Stock, of which 272,294,380 shares are issued and outstanding,
24,590,141 shares are reserved for issuance pursuant to issued and outstanding options, 12,658,298 shares are reserved for issuance
pursuant to securities (other than the aforementioned options) exercisable or exchangeable for, or convertible into, shares of
Common Stock, 3,286,444 shares are reserved for issuance under the Company’s 2019 Stock Incentive Plan, and 5,400,000 shares are
reserved for issuance under the Company’s 2020 Employee Stock Purchase Plan; and (ii) 10,000,000 shares of preferred stock,
par value $0.001 per share, none of which are outstanding. Other than as stated in the immediately preceding sentence, the Company
does not have any outstanding securities that are exercisable or exchangeable for, or convertible into, shares of Common Stock.
All of such outstanding shares are duly authorized and have been, or upon issuance will be, validly issued and are fully paid
and nonassessable. No securities of the Company are entitled to preemptive or similar rights, and no Person has any right of first
refusal, preemptive right, right of participation, or any similar right to participate in the transactions contemplated by the
Transaction Documents. There are no securities or instruments containing anti-dilution or similar provisions that will be triggered
by the issuance of the Securities. The Company does not have any stock appreciation rights or “phantom stock” or similar
plans or agreements currently outstanding except as disclosed above.


 


(f)              
Certain Fees. No brokerage or finder’s fees or commissions are or will be payable by the Subscribers to any broker, financial
advisor or consultant, finder, placement agent, investment banker, bank or other Person with respect to the transactions contemplated
by this Agreement as a result of an agreement entered into by the Company.


 


(g)             
Private Placement; No Integrated Offering; No General Solicitation; No Disqualification Events. Assuming in part the accuracy
of each Subscriber’s representations and warranties set forth in Section 3.2(c)-(g), (i) no registration under
the 1933 Act is required for the offer and sale of the Securities by the Company to the Subscribers under the Transaction Documents,
and (ii) the issuance and sale of the Securities hereunder does not contravene the rules and regulations of the Principal Market.
Assuming in part the accuracy of the Subscribers’ representations and warranties set forth in Section 3.2, neither the
Company, the Company Subsidiaries, any of their respective Affiliates, nor any Person acting on their behalf has, directly or
indirectly, made any offers or sales of any Company security or solicited any offers to buy any security, under circumstances
that would require registration of the issuance of any of the Securities under the 1933 Act, whether through integration with
prior offerings or otherwise or cause this offering of the Securities to require approval of stockholders of the Company for purposes
of the 1933 Act or any applicable stockholder approval provisions, including, without limitation, under the rules and regulations
of any exchange or automated quotation system on which any of the securities of the Company are listed or designated. Neither
the Company, the Company Subsidiaries nor their Affiliates, nor any Person acting on its or their behalf, has engaged in any form
of general solicitation or general advertising (within the meaning of Regulation D) in connection with the offer or sale of the
Securities. With respect to Securities to be offered and sold hereunder in reliance on Rule 506(b) under the 1933 Act (“Regulation
D Securities”), none of the Company, any of its predecessors, any affiliated issuer, any director, executive officer,
other officer of the Company participating in the offering hereunder, any beneficial owner of 20% or more of the Company’s outstanding
voting equity securities, calculated on the basis of voting power, nor any promoter (as that term is defined in Rule 405 under
the 1933 Act) connected with the Company in any capacity at the time of sale, nor any other Person covered by Rule 506(d) (each,
an “Issuer Covered Person” and, together, “Issuer Covered Persons”) is or has been subject to
any of the “Bad Actor” disqualifications described in Rule 506(d)(1)(i) to (viii) under the 1933 Act (a “Disqualification
Event”), except for a Disqualification Event covered by Rule 506(d)(2) or (d)(3). The Company has determined that no
Issuer Covered Person is subject to a Disqualification Event. The Company has complied, to the extent applicable, with its disclosure
obligations under Rule 506(e), and has furnished to the Subscribers a copy of any disclosures provided thereunder. No Person has
been or will be paid (directly or indirectly) remuneration for solicitation of Subscribers or potential purchasers in connection
with the sale of any Regulation D Securities.


 






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(h)             
Application of Takeover Protections. The Company and its Board of Directors have taken all necessary action, if any, in
order to render inapplicable any control share acquisition, interested stockholder, business combination, poison pill (including
any distribution under a rights agreement, or similar arrangement or plan) or other similar anti-takeover provision under the
Company’s articles of incorporation and bylaws, each as amended, that is or could become applicable to the Subscribers as a result
of the Subscribers and the Company fulfilling their obligations or exercising their rights under the Transaction Documents, including
without limitation as a result of the Company’s issuance of the Securities and the Subscribers’ ownership of the Securities. The
Company and its Board of Directors have taken all necessary action, if any, in order to render inapplicable any stockholder rights
plan or similar arrangement now in effect relating to accumulations of beneficial ownership of shares of Common Stock or a change
in control of the Company or any Company Subsidiary.


 


(i)               
Transfer Taxes. On the Closing Date, all stock transfer or other taxes (other than income or similar taxes) which are required
to be paid in connection with the sale and transfer of the Securities to be sold to each Subscriber hereunder will be, or will
have been, fully paid or provided for by the Company, and all laws imposing such taxes will be or will have been complied with.


 


(j)               
Investment Company Status. Neither the Company nor any Company Subsidiary is, and upon consummation of the sale of the
Securities, will not be, an “investment company,” a company controlled by an “investment company” or an “affiliated
person” of, or “promoter” or “principal underwriter” for, an “investment company” as such terms
are defined in the Investment Company Act of 1940, as amended.


 


(k)             
U.S. Real Property Holding Corporation. The Company is not and has never been a U.S. real property holding corporation
within the meaning of Section 897 of the Internal Revenue Code of 1986, as amended, and the Company shall so certify upon any
Subscriber’s request.


 






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(l)               
Loan Documents. The Company hereby acknowledges and agrees that each of the Transaction Documents constitutes a “Loan
Document” under the Financing Agreement, including for purposes of determining an Event of Default under the Financing Agreement.


 


3.2          Representations and Warranties of the Subscribers. Each Subscriber hereby, as to itself only and for no other Subscriber,
represents and warrants as of the date hereof and as of the Closing Date (except for representations and warranties that speak
as of a specific date, which shall be made as of such date) to the Company as follows:


 


(a)             
Organization; Authority. Such Subscriber is an entity duly organized, validly existing and in good standing under the laws
of the jurisdiction of its organization with the requisite power and authority to enter into and to consummate the transactions
contemplated by the Transaction Documents and otherwise to carry out its obligations hereunder and thereunder. The execution,
delivery and performance by such Subscriber of the Transaction Documents to which it is a party have been duly authorized by all
necessary action on the part of such Subscriber. Each of the Transaction Documents to which such Subscriber is a party has been
duly executed by such Subscriber and, when delivered by such Subscriber in accordance with terms hereof, will constitute the valid
and legally binding obligation of such Subscriber, enforceable against it in accordance with its terms, except as such enforceability
may be limited by general principles of equity or applicable bankruptcy, insolvency, reorganization, moratorium, liquidation or
similar laws relating to, or affecting generally, the enforcement of applicable creditors’ rights and remedies.


 


(b)             
No Conflicts. The execution, delivery and performance of the Transaction Documents by such Subscriber and the consummation
by such Subscriber of the transactions contemplated hereby and thereby do not and will not (i) conflict with or violate any
provision of such Subscriber’s certificate or articles of incorporation, bylaws or other organizational or charter documents,
(ii) conflict with, or constitute a default (or an event which with notice or lapse of time or both would become a default) under,
or give to others any rights of termination, amendment, acceleration or cancellation of, any agreement, indenture or instrument
to which such Subscriber is a party or by which any property or asset of such Subscriber is bound or affected, or (iii) result
in a violation of any law, rule, regulation, order, judgment, injunction, decree or other restriction of any Governmental Authority
to which such Subscriber is subject (including, without limitation, foreign, federal and state securities laws and regulations);
except in the case of clause (ii) or (iii) above, as would not, reasonably be expected to have, individually or in the aggregate,
a material adverse effect on the ability of the Subscriber to perform its obligations thereunder.


 


(c)             
Investment Intent. Such Subscriber is acquiring the Securities as principal for its own account for investment purposes
and not with a view to distributing or reselling such Securities or any part thereof in violation of applicable securities laws,
without prejudice, however, to such Subscriber’s right at all times to sell or otherwise dispose of all or any part of such Securities
in compliance with applicable federal and state securities laws. Nothing contained herein shall be deemed a representation or
warranty by such Subscriber to hold the Securities for any period of time. Notwithstanding the foregoing, such Subscriber understands
that the Securities have not been registered under the 1933 Act, and therefore the Securities may not be sold, assigned or transferred
unless pursuant to (i) an effective registration statement under the 1933
Act with respect thereto or (ii) an available exemption from the registration
requirements of the 1933 Act. Such Subscriber has been advised or is aware of the provisions of Rule 144 promulgated under the
1933 Act (or a successor rule thereto) (collectively, “Rule 144”) as in effect from time to time, which permit
limited resale of shares purchased in a private placement subject to the satisfaction of certain conditions.


 






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(d)             
Subscriber Status. At the time such Subscriber was offered the Securities, it was, and at the date hereof it is, and on
each date on which it exercises the Warrants it will be, an “accredited investor” as defined in Rule 501(a) under the
1933 Act.


 


(e)             
Experience of such Subscriber. Such Subscriber, either alone or together with its representatives, has such knowledge,
sophistication and experience in business and financial matters so as to be capable of evaluating the merits and risks of the
prospective investment in the Securities, and has so evaluated the merits and risks of such investment. Such Subscriber is able
to bear the economic risk of an investment in the Securities and, at the present time, is able to afford a complete loss of such
investment.


 


(f)              
General Solicitation. Such Subscriber is not purchasing the Securities as a result of any advertisement, article, notice
or other communication regarding the Securities published in any newspaper, magazine or similar media or broadcast over television
or radio or presented at any seminar or, to such Subscriber’s knowledge, any other general solicitation or general advertisement.


 


(g)             
Access to Data. Such Subscriber has received and reviewed information about the Company and has had an opportunity to discuss
the Company’s business, management and financial affairs with its management and to review the Company’s facilities. Such Subscriber
acknowledges that it has been afforded (i) the opportunity to ask such questions as it has deemed necessary of, and to receive
answers from, representatives of the Company concerning the terms and conditions of the offering of the Securities and the merits
and risks of investing in the Securities; (ii) access to information about the Company and its respective financial condition,
results of operations, business, properties, management and prospects sufficient to enable it to evaluate its investment; and
(iii) the opportunity to obtain such additional information that the Company possesses or can acquire without unreasonable
effort or expense that is necessary to make an informed investment decision with respect to the investment. In deciding to enter
into this Agreement and the transactions contemplated hereby, such Subscriber has not relied upon any representations and warranties
other than the express representations and warranties contained in the Loan Documents. The foregoing, however, does not limit
or modify the representations and warranties made by the Company in this Agreement or any other provision in this Agreement or
the right of the Subscribers to rely thereon. Such Subscriber has sought such accounting, legal and tax advice as it has considered
necessary to make an informed decision with respect to its acquisition of the Securities.


 


(h)             
Transfer or Resale. Such Subscriber understands that: (i) the Securities have not been and are not being registered under
the 1933 Act or any state securities laws, and may not be offered for sale, sold, assigned or transferred unless (A) subsequently
registered thereunder, (B) such Subscriber shall have delivered to the Company (if requested by the Company) an opinion of counsel
to such Subscriber, reasonably satisfactory to the Company as to such counsel and to the form of opinion, to the effect that such
Securities may be sold, assigned or transferred without registration under the applicable requirements of the 1933 Act; provided,
however, that Schulte Roth & Zabel LLP shall be deemed reasonably satisfactory to the Company; provided, further,
that no such opinion shall be required to sell, assign or otherwise transfer all or any portion of such Securities to an Affiliate
of the holder of the Securities, or (C) such Subscriber provides the Company with assurance reasonably satisfactory to the Company
that such Securities can be sold, assigned or transferred pursuant to Rule 144 or to an accredited investor in a private transaction
exempt from the registration requirements of the 1933 Act; (ii) any sale of the Securities made in reliance on Rule 144 may
be made only in accordance with the terms of Rule 144; and (iii) neither the Company nor any other Person is under any obligation
to register the Securities under the 1933 Act or any state securities laws or to comply with the terms and conditions of any exemption
thereunder.


 






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(i)               
Reliance on Exemptions. Such Subscriber understands that the Securities are being offered and sold to it in reliance on
specific exemptions from the registration requirements of United States federal and state securities laws and that the Company
is relying in part upon the truth and accuracy of, and such Subscriber’s compliance with, the representations, warranties, agreements,
acknowledgements and understandings of such Subscriber set forth herein in order to determine the availability of such exemptions
and the eligibility of such Subscriber to acquire the Securities.


 


(j)               
No Governmental Review. Such Subscriber understands that no United States federal or state agency or any other government
or governmental agency has passed on or made any recommendation or endorsement of the Securities or the fairness or suitability
of the investment in the Securities nor have such authorities passed upon or endorsed the merits of the offering of the Securities.


 


(k)             
Legends. Such Subscriber understands that the certificates or other instruments representing the Warrants and the stock
certificates representing the Warrant Shares, except as set forth below, shall bear a restrictive legend in substantially the
following form (and a stop-transfer order may be placed against transfer of such stock certificates):


 


[NEITHER
THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS WARRANT NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE EXERCISABLE
HAVE BEEN][THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN] REGISTERED UNDER THE SECURITIES ACT OF
1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED
IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR THE SECURITIES UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR
(B) AN OPINION OF COUNSEL SELECTED BY THE HOLDER, IN A FORM REASONABLY SATISFACTORY TO THE COMPANY, THAT REGISTRATION IS NOT REQUIRED
UNDER SAID ACT. NOTWITHSTANDING THE FOREGOING, THE SECURITIES MAY BE PLEDGED IN CONNECTION WITH A BONA FIDE MARGIN ACCOUNT OR
OTHER LOAN OR FINANCING ARRANGEMENT SECURED BY THE SECURITIES.


 


 



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The
legend set forth above shall be removed and the Company shall issue a certificate without such legend to the holder of the Securities
upon which it is stamped or issue to such holder by electronic delivery at the applicable balance account at The Depository Trust
Company (“DTC”), if (i) such Securities are registered for resale under the 1933 Act and the holder has delivered
to the Company a representation that such Securities have been sold pursuant to such registration statement, or (ii) in connection
with a sale, assignment or other transfer, such holder provides the Company with an opinion of counsel, reasonably satisfactory
to the Company as to such counsel and to the form of opinion, to the effect that such sale, assignment or transfer of the Securities
may be made (or was made, as applicable under Rule 144) without registration under the applicable requirements of the 1933 Act;
provided, however, that Schulte Roth & Zabel LLP shall be deemed reasonably satisfactory to the Company; provided,
further, that no such opinion shall be required to sell, assign or otherwise transfer all or any portion of such Securities
to an Affiliate of the holder of the Securities. The Company shall be responsible for the fees of its transfer agent and all DTC
fees associated with such issuance.


 


The
Company acknowledges and agrees that no Subscriber makes or has made any representations or warranties with respect to the transactions
contemplated hereby or by any other Transaction Document other than those specifically set forth in Section 3.2.


 


ARTICLE
IV.

OTHER AGREEMENTS OF THE PARTIES


 


4.1          Register; Pledge.


 


(a)             
The Company shall maintain at its principal executive offices (or such other office or agency of the Company as it may designate
by notice to each holder of Securities), a register for each series of the Warrants in which the Company shall record the name
and address of the Person in whose name the Warrants have been issued (including the name and address of each permitted transferee)
the number of Warrant Shares issuable upon exercise of the Warrants held by such Person. The Company shall keep the register open
and available at all times during business hours upon reasonable notice for inspection of any Subscriber or its legal representatives.


 


(b)             
The Company acknowledges and agrees that a Subscriber may from time to time pledge or grant a security interest in some or all
of the Securities in connection with a bona fide margin agreement secured by the Securities and, if required under the terms of
such agreement, such Subscriber may transfer pledged or secured Securities to the pledgees or secured parties. Such a pledge or
transfer would not be subject to approval of the Company and no legal opinion of the pledgee, secured party or pledgor shall be
required in connection therewith. Further, no notice shall be required of such pledge. At the appropriate Subscriber’s expense,
the Company will execute and deliver such reasonable documentation as a pledgee or secured party of Securities may reasonably
request in connection with a pledge or transfer of the Securities.


 






    -11- 


     


    

 


4.2          Integration. The Company shall not, and shall use its reasonable best efforts to ensure that no Affiliate of the Company
shall, sell, offer for sale or solicit offers to buy or otherwise negotiate in respect of any security (as defined in Section 2
of the 1933 Act) that would be integrated with the offer or sale of the Securities in a manner that would require the registration
under the 1933 Act of the sale of the Securities to the Subscribers or that would be integrated with the offer or sale of the
Securities for purposes of the rules and regulations of the Principal Market.


 


4.3          Reservation and Listing of Securities. So long as any Subscriber owns any Warrants, the Company shall take all action necessary
to at all times after the date hereof have authorized, and reserved for the purpose of issuance, no less than 100% of the number
of shares of Common Stock issuable upon exercise of the Warrants then outstanding (without taking into account any limitations
on the exercise of the Warrants set forth in the Warrants).


 


4.4          Form D and Blue Sky. The Company shall file a Form D with respect to the Securities as required under Regulation D. The
Company shall, on or before the Closing Date, take such action as the Company shall reasonably determine is necessary in order
to obtain an exemption for, or to, qualify the Securities for sale to the Subscribers at the Closing pursuant to this Agreement
under applicable securities or “Blue Sky” laws of the states of the United States (or to obtain an exemption from such
qualification), and shall provide evidence of any such action so taken to the Subscribers on or prior to the Closing Date. Without
limiting any other obligation of the Company under this Agreement, the Company shall timely make all filings and reports relating
to the offer and sale of the Securities required under all applicable securities laws (including, without limitation, all applicable
federal securities laws and all applicable “Blue Sky” laws), and the Company shall comply with all applicable federal,
state and local laws, statutes, rules, regulations and the like relating to the offering and sale of the Securities to the Subscribers.


 


4.5          Indemnification. In consideration of each Subscriber’s execution and delivery of the Transaction Documents and acquiring
the Securities thereunder and in addition to all of the Company’s other obligations under the Transaction Documents, the Company
shall defend, protect, indemnify and hold harmless each Subscriber and each other holder of the Warrants and all of their shareholders,
partners, members, officers, directors, employees and investors and any of the foregoing Persons’ agents or other representatives
(including, without limitation, those retained in connection with the transactions contemplated by this Agreement) (collectively,
the “Indemnitees”) from and against any and all actions, causes of action, suits, claims, losses, costs, penalties,
fees, liabilities and damages, and expenses in connection therewith (irrespective of whether any such Indemnitee is a party to
the action for which indemnification hereunder is sought), and including reasonable attorneys’ fees and disbursements (the “Indemnified
Liabilities”), incurred by any Indemnitee as a result of, or arising out of, or relating to (a) any misrepresentation
or breach of any representation or warranty made by the Company in the Transaction Documents, (b) any breach of any covenant,
agreement or obligation of the Company contained in the Transaction Documents, or (c) any cause of action, suit or claim brought
or made against such Indemnitee by a third party (including for these purposes a derivative action brought on behalf of the Company)
and arising out of or resulting from (i) the execution, delivery, performance or enforcement of the Transaction Documents,
or (ii) the status of such Subscriber as an investor in the Company pursuant to the transactions contemplated by the Transaction
Documents. For the avoidance of doubt, clauses (a) and (b) of the preceding sentence are intended to apply, and shall apply, to
direct claims asserted by any Subscriber against the Company as well as any third party claims asserted by an Indemnitee (other
than a Subscriber) against the Company. To the extent that the foregoing undertaking by the Company may be unenforceable for any
reason, the Company shall make the maximum contribution to the payment and satisfaction of each of the Indemnified Liabilities
which is permissible under applicable law. NOTWITHSTANDING ANYTHING TO THE CONTRARY IN ANY TRANSACTION DOCUMENT, THE COMPANY SHALL
HAVE NO OBLIGATION TO ANY INDEMNITEE HEREUNDER WITH RESPECT TO (I) ANY INDEMNIFIED LIABILITIES TO THE EXTENT SUCH INDEMNIFIED
LIABILITIES ARISE FROM THE GROSS NEGLIGENCE OR WILLFUL MISCONDUCT, AS DETERMINED BY A COURT OF COMPETENT JURISDICTION IN A FINAL
ORDER SUBJECT TO NO FURTHER APPEAL, OF THAT INDEMNITEE OR ANY OF ITS AFFILIATES OR (II) ANY SPECIAL, PUNITIVE OR CONSEQUENTIAL
DAMAGES RELATING TO ANY TRANSACTION DOCUMENT OR ARISING OUT OF ITS ACTIVITIES IN CONNECTION HEREWITH OR THEREWITH (WHETHER BEFORE
OR AFTER THE CLOSING DATE).


 






    -12- 


     


    

 


ARTICLE
V.

CLOSING DELIVERABLES


 


5.1          Closing Deliverables of the Company. At the Closing, the Company shall deliver to the Investors the following:


 


(a)            Representations and Warranties; Certificates. The representations and warranties of the Company shall be true and correct
in all material respects as of the date when made and as of the Closing Date as though made at that time (except for representations
and warranties that speak as of a specific date which shall be true and correct as of such specified date) and the Company shall
have performed, satisfied and complied in all material respects with the covenants, agreements and conditions required by the
Transaction Documents to be performed, satisfied or complied with by the Company at or prior to the Closing Date. Such Subscriber
shall have received a certificate, executed by the Chief Executive Officer of the Company, dated as of the Closing Date, to the
foregoing effect and as to such other matters as may be reasonably requested by such Subscriber, in the form attached hereto as
Exhibit B. In addition, such Subscriber shall have received a certificate, executed by the Secretary or other applicable
officer of the Company, dated as of the Closing Date, as to the resolutions consistent with Section 3.1(a) as adopted by the Company’s
Board of Directors in a form reasonably acceptable to such Subscriber and the incumbency and specimen signature of each officer
of the Company who may sign this Agreement and the other Transaction Documents, in the form attached hereto as Exhibit C.


 


(b)            Transaction Documents. The Company shall have duly executed and delivered to such Subscriber (i) each of the Transaction
Documents to which it is a party and (ii) Warrants for such aggregate number of shares of Common Stock as is set forth across
from such Subscriber’s name in column (3) of the Schedule of Subscribers.


 


(c)            Legal Opinion. Such Subscriber shall have received the opinion of DLA Piper LLP (US), the Company’s outside counsel, dated
as of the Closing Date, in the form and substance reasonably acceptable to the Subscribers.


 






    -13- 


     


    

 


ARTICLE
VI.

MISCELLANEOUS


 


6.1          Fees and Expenses. The Company shall reimburse the Designee or its designee(s) (in addition to any other expense amounts
paid to any Subscriber prior to the date of this Agreement) for all reasonable and documented actual costs and expenses incurred
in connection with the transactions contemplated by the Transaction Documents (including all reasonable and documented legal fees
and disbursements in connection therewith and documentation and implementation of the transactions contemplated by the Transaction
Documents) on or prior to the Closing, which amount shall be paid by the Company at the Closing. The Company shall pay, and hold
each Subscriber harmless against, any liability, loss or expense (including, without limitation, reasonable attorney’s fees and
out-of-pocket expenses) arising in connection with any claim relating to any placement agent’s fees, financial advisory fees,
or broker’s commissions (other than for any Persons engaged by any Subscriber) relating to or arising out of the transactions
contemplated hereby as a result of an agreement entered into by the Company. Except as otherwise set forth in the Transaction
Documents, each party to this Agreement shall bear its own expenses in connection with the sale of the Securities to the Subscribers.


 


6.2          Entire Agreement; Amendments. This Agreement and the other Transaction Documents supersede all other prior oral or written
agreements between the Subscribers, the Company, their affiliates and Persons acting on their behalf with respect to the matters
discussed herein, and this Agreement, the other Transaction Documents and the instruments referenced herein and therein contain
the entire understanding of the parties with respect to the matters covered herein and therein and, except as specifically set
forth herein or therein, neither the Company nor any Subscriber makes any representation, warranty, covenant or undertaking with
respect to such matters. No provision of this Agreement may be amended other than by an instrument in writing signed by the Company
and the Required Holders, and any amendment to this Agreement made in conformity with the provisions of this Section 6.2
shall be binding on all Subscribers and holders of Warrants. No provision hereof may be waived other than by an instrument in
writing signed by the party against whom enforcement is sought. No such amendment shall be effective to the extent that it applies
to less than all of the holders of Warrants then outstanding. The Company has not, directly or indirectly, made any agreements
with any Subscribers relating to the terms or conditions of the transactions contemplated by the Transaction Documents except
as set forth in the Transaction Documents. Without limiting the foregoing, the Company confirms that, except as set forth in this
Agreement and the Financing Agreement, no Subscriber has made any commitment or promise or has any other obligation to provide
any financing to the Company or otherwise. No consideration shall be offered or paid to any Person to amend or consent to a waiver
or modification of any provision of any of the Transaction Documents unless the same consideration (other than the reimbursement
of legal fees) also is offered to all of the parties to the Transaction Documents or holders of the Warrants, as the case may
be.


 






    -14- 


     


    

 


6.3          Notices. Any notices, consents, waivers or other communications required or permitted to be given under the terms of this
Agreement must be in writing and will be deemed to have been delivered: (a) upon delivery, when delivered personally; (b) upon
confirmation of delivery, when sent by electronic mail; or (c) upon delivery or refusal of delivery when sent via a nationally
recognized overnight delivery service, in each case properly addressed to the party to receive the same. The addresses, facsimile
numbers and email addresses for such communications shall be:


 


	If
    to the Company:	TherapeuticsMD,
Inc. 

        951
Yamato Road, Suite 220 

        Boca
Raton, FL 33431 

        Attention: General
Counsel 

         

	 
	With
    a copy (for information purposes only) to:	DLA
Piper LLP (US) 

        200
South Biscayne Boulevard 

        Suite
2500 

        Miami,
FL 33131 

        Attention:
 Joshua M. Samek, Esq.

         

	 
	If
    to a Subscriber:	To
    its address set forth on the Schedule of Subscribers, with copies to such Subscriber’s representatives as set forth
    on the Schedule of Subscribers.
	 	 
	With
    a copy (for information purposes only) to:	Schulte
Roth & Zabel LLP 

        919
Third Avenue 

        New
York, NY 10022 

        Attention:
F. Xavier Kowalski 



 


or
such other address as may be designated in writing hereafter, in the same manner, by such Person by two (2) Business Days’ prior
notice to the other party in accordance with this Section 6.3. Written confirmation of receipt (i) given by the recipient
of such notice, consent, waiver or other communication, or (ii) provided by a courier or overnight courier service shall be rebuttable
evidence of personal service or receipt from a nationally recognized overnight delivery service in accordance with clause (a)
or (c) above, respectively.


 


6.4              
Construction. The headings herein are for convenience only, do not constitute a part of this Agreement and shall not be
deemed to limit or affect any of the provisions hereof. No specific representation or warranty shall limit the generality or applicability
of a more general representation or warranty. The parties agree that each of them and/or their respective counsel has reviewed
and had an opportunity to revise the Transaction Documents and, therefore, the normal rule of construction to the effect that
any ambiguities are to be resolved against the drafting party shall not be employed in the interpretation of the Transaction Documents
or any amendments hereto.


 


6.5              
Successors and Assigns. This Agreement shall be binding upon and inure to the benefit of the parties and their successors
and permitted assigns. The Company may not assign this Agreement or any rights or obligations hereunder without the prior written
consent of the Subscribers, except in connection with a Fundamental Transaction (as defined in the Warrant). Any Subscriber may
assign its rights under this Agreement to any Person to whom such Subscriber assigns or transfers any Warrants, provided such
transferee (i) agrees in writing in favor of the Company to be bound, with respect to the transferred Warrants, by the provisions
hereof and of the applicable Transaction Documents that apply to the “Subscribers” and (ii) is not a Disqualified Institution
(as defined in the Financing Agreement). Notwithstanding anything to the contrary herein, Securities may be pledged to any Person
in connection with a bona fide margin account or other loan or financing arrangement secured by such Securities.


 






    -15- 


     


    

 


6.6              
No Third-Party Beneficiaries. This Agreement is intended for the benefit of the parties hereto and their respective successors
and permitted assigns and is not for the benefit of, nor may any provision hereof be enforced by, any other Person, except that
each Indemnitee is an intended third party beneficiary of Section 4.5 and may enforce the provisions of such Sections directly
against the parties with obligations thereunder.


 


6.7              
Governing Law; Venue; Waiver of Jury Trial. This Agreement and the Warrants shall be governed by and construed and enforced
in accordance with, and all questions concerning the construction, validity, interpretation and performance of this Agreement
and the Warrants shall be governed by the internal laws of the State of New York, without giving effect to any choice of law or
conflict of law provision or rule (whether of the State of New York or any other jurisdictions) that would cause the application
of the laws of any jurisdictions other than the State of New York (except for matters governed by corporate law in the State of
Nevada). The Company, each Subscriber and each holder of a Warrant, by acceptance thereof, agrees that all legal proceedings concerning
the interpretations, enforcement and defense of the transactions contemplated by this Agreement and the Warrant (whether brought
against any such party or its respective affiliates, directors, officers, stockholders, employees or agents) shall be commenced
exclusively in the state and federal courts sitting in the City of New York, Borough of Manhattan. The Company, each Subscriber
and each holder of a Warrant, by acceptance thereof, hereby irrevocably submits to the exclusive jurisdiction of the state and
federal courts sitting in the City of New York, Borough of Manhattan for the adjudication of any dispute hereunder or in connection
herewith or with any transaction contemplated hereby or discussed herein (including with respect to the enforcement of this Agreement
or a Warrant) and hereby irrevocably waives and agrees not to assert in any suit, action or proceeding, any claim that it is not
personally subject to the jurisdiction of any such court, that such suit, action or proceeding is brought in an inconvenient forum
or that the venue of such suit, action or proceeding is improper. THE COMPANY, EACH SUBSCRIBER AND EACH HOLDER OF A WARRANT,
BY ACCEPTANCE THEREOF, HEREBY IRREVOCABLY WAIVES ANY RIGHT IT MAY HAVE TO, AND AGREES NOT TO REQUEST, A JURY TRIAL FOR THE ADJUDICATION
OF ANY DISPUTE HEREUNDER OR IN CONNECTION WITH OR ARISING OUT OF THIS AGREEMENT, A WARRANT OR ANY TRANSACTION CONTEMPLATED HEREBY
OR THEREBY.


 


6.8              
Survival. The representations, warranties, agreements and covenants contained herein shall survive the Closing and the
delivery and/or exercise of the Warrants, as applicable.


 


6.9              
Execution. This Agreement may be executed in two or more counterparts, all of which when taken together shall be considered
one and the same agreement and shall become effective when counterparts have been signed by each party and delivered to the other
party, it being understood that both parties need not sign the same counterpart. In the event that any signature is delivered
by facsimile transmission or by an e-mail which contains a portable document format (.pdf) filed of an executed signature page,
such signature page shall create a valid and binding obligation of the party executing (or on whose behalf such signature is executed)
the same with the same force and effect as if such signature page were an original thereof.


 






    -16- 


     


    

 


6.10           
Severability. If any provision of a Transaction Document is prohibited by law or otherwise determined to be invalid or
unenforceable by a court of competent jurisdiction, the provision that would otherwise be prohibited, invalid, or unenforceable
shall be deemed amended to apply to the broadest extent that it would be valid and enforceable, and the invalidity or unenforceability
of such provision shall not affect the validity of the remaining provisions of the Transaction Document so long as the Transaction
Document as so modified continues to express, without material change, the original intentions of the parties as to the subject
matter hereof or thereof and the prohibited nature, invalidity or unenforceability of the provision(s) in question does not substantially
impair the respective expectations or reciprocal obligations of the parties or the practical realization of the benefits that
would otherwise be conferred upon the parties. The parties will endeavor in good faith negotiations to replace the prohibited,
invalid, or unenforceable provision(s) with a valid provision(s), the effect of which comes as close as possible to that of the
prohibited, invalid or unenforceable provision(s).


 


6.11           
Rescission and Withdrawal Right. Notwithstanding anything to the contrary contained in (and without limiting any similar
provisions of) the Transaction Documents, whenever any Subscriber exercises a right, election, demand or option under a Transaction
Document and the Company does not timely perform its related obligations within the periods therein provided, then such Subscriber
may rescind or withdraw, in its sole discretion from time to time upon written notice to the Company, any relevant notice, demand
or election in whole or in part without prejudice to its future actions and rights.


 


6.12           
Remedies. In addition to being entitled to exercise all rights provided herein or granted by law, including recovery of
damages, the Company, each Subscriber and each holder of a Warrant, by acceptance thereof, will be entitled to specific performance
under the Transaction Documents. Any Person having any rights under any provision of any Transaction Document shall be entitled
to enforce such rights specifically (without posting a bond or other security), to recover damages by reason of any breach of
any provision of the Transaction Document and to exercise all other rights granted by law. Furthermore, the Company, each Subscriber
and each holder of a Warrant, by acceptance thereof, recognize that in the event that it fails to perform, observe, or discharge
any or all of its obligations under the Transaction Documents, any remedy at law may prove to be inadequate relief to the other
parties. Each of such parties therefore agrees that the other parties shall be entitled to seek specific performance and/or temporary,
preliminary and permanent injunctive or other equitable relief from any court of competent jurisdiction in any such case without
the necessity of showing economic loss and without any bond or other security being required.


 


6.13           
Payment Set Aside. To the extent that the Company makes a payment or payments to any Subscriber hereunder or pursuant to
any of the other Transaction Documents or any Subscriber enforces or exercises its rights hereunder or thereunder, and such payment
or payments or the proceeds of such enforcement or exercise or any part thereof are subsequently invalidated, declared to be fraudulent
or preferential, set aside, recovered from, disgorged by or are required to be refunded, repaid or otherwise restored to the Company
or any Company Subsidiary by a trustee, receiver or any other person under any law (including, without limitation, any bankruptcy
law, state or federal law, common law or equitable cause of action), then to the extent of any such restoration the obligation
or part thereof originally intended to be satisfied shall be revived and continued in full force and effect as if such payment
had not been made or such enforcement or setoff had not occurred.


 






    -17- 


     


    

 


6.14           
Further Assurances. The Company, each Subscriber and each holder of a Warrant, by acceptance thereof, shall do and perform,
or cause to be done and performed, all such further acts and things, and shall execute and deliver all such other agreements,
certificates, instruments and documents, as any other party may reasonably request in order to carry out the intent and accomplish
the purposes of this Agreement and the consummation of the transactions contemplated hereby.


 


6.15           
Replacement of Securities. If any certificate or instrument evidencing any Securities is mutilated, lost, stolen or destroyed,
the Company shall issue or cause to be issued in exchange and substitution for and upon cancellation thereof, or in lieu of and
substitution therefor, a new certificate or instrument, but only upon receipt of evidence reasonably satisfactory to the Company
of such loss, theft or destruction and customary and reasonable indemnity, if requested. The applicants for a new certificate
or instrument under such circumstances shall also pay any reasonable third-party costs associated with the issuance of such replacement
Securities.


 


[REMAINDER
OF PAGE INTENTIONALLY LEFT BLANK

SIGNATURE PAGES FOLLOW]


 




    -18- 


     


    

 


IN
WITNESS WHEREOF, each Subscriber and the Company have caused their respective signature page to this Agreement to be duly
executed as of the date first written above.


 





	 	COMPANY:
	 	 	 
	 	THERAPEUTICSMD, INC.
	 	 	 
	 	By:	/s/ Robert G. Finizio
	 	 	Name: Robert G. Finizio
	 	 	Title: Chief Executive Officer










 





[Signature Page to
Subscription Agreement]




 




     


     


    

 


 


IN
WITNESS WHEREOF, each Subscriber and the Company have caused their respective signature page to this Agreement to be duly
executed as of the date first written above.


 





	 	SUBSCRIBER:
	 	 	 
	 	Sixth
    Street Specialty Lending, Inc.
	 	 	 
	 	By:	/s/ Joshua
    Easterly
	 	 	Name: Joshua Easterly
	 	 	Title: Chief Executive Officer





 


[Signature Page to
Subscription Agreement]


 




     


     


    

 


IN
WITNESS WHEREOF, each Subscriber and the Company have caused their respective signature page to this Agreement to be duly
executed as of the date first written above.


 


	 	SUBSCRIBER:
	 	 	 
	 	Redwood
    IV Finance 1, LLC
	 	 	 
	 	By:	/s/ Joshua
    Peck
	 	 	Name: Joshua Peck
	 	 	Title: Vice President





 


[Signature Page to
Subscription Agreement]


 




     


     


    

 


IN
WITNESS WHEREOF, each Subscriber and the Company have caused their respective signature page to this Agreement to be duly
executed as of the date first written above.


 





	 	SUBSCRIBER:
	 	 	 
	 	TAO
    Finance 1, LLC
	 	 	 
	 	By:	/s/ Joshua
    Peck
	 	 	Name: Joshua Peck
	 	 	Title: Vice President


  


[Signature Page to
Subscription Agreement]


 




     


     


    

 


SCHEDULE
OF SUBSCRIBERS


 


	(1)	(2)	(3)	(4)
	 	 	 	 
	Subscriber	Address
    and Facsimile Number	Number
of

        Warrant
Shares
	Legal
    Representative’s

    Address and Facsimile Number
	 	 	 	 
	Sixth
    Street Specialty Lending, Inc.	2100
McKinney Ave, Suite 1500 

        Dallas
Texas 75201 

        Attn:
Joshua Peck; Sixth Street Legal 
	712,817	Schulte
    Roth & Zabel LLP

    919 Third Avenue

    New York, New York  10022

    Attention: F. Xavier Kowalski
	 	 	 	 
	Redwood
    IV Finance 1, LLC	2100
McKinney Ave, Suite 1500 

        Dallas
Texas 75201 

        Attn:
Joshua Peck; Sixth Street Legal 

         

         
	1,188,029	Schulte
    Roth & Zabel LLP

    919 Third Avenue

    New York, New York  10022

    Attention: F. Xavier Kowalski
	TAO
    Finance 1, LLC	2100
McKinney Ave, Suite 1500 

        Dallas
Texas 75201 

        Attn:
Joshua Peck; Sixth Street Legal
	2,851,270	Schulte
    Roth & Zabel LLP

    919 Third Avenue

    New York, New York  10022

    Attention: F. Xavier Kowalski


  




     


     


    

 


EXHIBIT
A


 


Warrants


 


(See
attached)


 


 




     


     


    

 


EXHIBIT
B


 


Officer’s
Certificate


 


(See
attached)


 




     


     


    

 


EXHIBIT
C 


 


Secretary’s
Certificate


 


(See
attached)