Document:

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)TherapeuticsMD, Inc. 10-Q

Exhibit
10.6

EMPLOYMENT
AGREEMENT

THIS
EMPLOYMENT AGREEMENT (this “Agreement”), by and between TherapeuticsMD, Inc., a Nevada corporation (the
“Company”), and James C. D’Arecca (“Executive”) is entered into and effective as of the
1st day of June 2020 (the “Effective Date”).

WHEREAS,
the Company and Executive now wish to provide for terms and conditions of Executive’s continued employment with the Company,
pursuant to the terms and conditions set forth in this Agreement.

NOW,
THEREFORE, in consideration of the premises and of the mutual covenants set forth in this Agreement, the parties hereto agree
as follows:

1.            Employment and Duties.

(a)         Employment
and Term. The Company hereby agrees to employ Executive, and Executive hereby agrees to serve the Company, in accordance with
the terms and conditions set forth herein, for a period of three (3) years, commencing as of the Effective Date (such three (3)
year period, as it may be extended pursuant to this Section 1(a), the “Term”), unless sooner terminated
pursuant to Section 3 hereof. Commencing on the third anniversary of the Effective Date, and each anniversary thereafter,
the Term shall automatically be extended for one (1) additional year, unless at least ninety (90) days prior to such anniversary,
the Company or Executive shall have given notice in accordance with Section 8 hereof that it or Executive does not
wish to extend the Term.

(b)         Duties of Executive. Executive
shall serve as the Chief Financial Officer of the Company, shall diligently perform all services as may be reasonably assigned
to Executive by the Company’s Board of Directors (the “Board”) or the Company’s Chief Executive
Officer (the “CEO”), of if delegated by the CEO the President of the Company or the Executive Vice President
of Operations (the “President or EVP, Operations”). Executive shall exercise such power and authority as may
from time to time be delegated to Executive by the Board, the CEO, and the President or EVP, Operations. Executive shall
report solely and directly to the CEO (or to the President or EVP, Operations if instructed to by the CEO). During Executive’s
employment, Executive shall devote substantially all of Executive’s full business time, energy, and ability exclusively
to the business and interests of the Company, shall generally be physically present at the Company’s offices in Boca Raton,
Florida during normal business hours each week (other than permitted periods of working remotely, paid time off (“PTO”)
and on appropriate business travel for the benefit of the Company and shall not, without the Company’s prior written consent,
be engaged in any other business activity pursued for gain, profit, or other pecuniary advantage if such activity interferes in
any material respect with Executive’s duties and responsibilities hereunder. In Executive’s capacity as the Chief
Financial Officer of the Company, Executive shall do and perform all services, acts, or things necessary or advisable to manage
and conduct the business of the Company, subject to the policies and procedures set by the Company, including
but not limited to performing the Company’s budgeting and forecasting, record keeping, internal and external reporting; performing
financial risk management; managing – in conjunction with the CEO – the Company’s internal relations functions;
managing the Company’s fundraising plans and capital structure; maintaining the Company’s SOX compliance program, managing the
Company’s cash flow, overseeing the Company’s finance systems; managing taxes, treasury, and other functions, and managing the
finance organization. Except as otherwise agreed in writing by the Company, it shall not be a violation of this Agreement
for Executive, and Executive shall be permitted, to (i) serve on any civic or charitable boards; (ii) deliver lectures, fulfill
speaking engagements, or teach at educational institutions and other institutions; (iii) subject to any applicable Company policies,
make personal investments in such form or manner as will neither require Executive’s services in the operation or affairs
of the companies or enterprises in which such investments are made nor subject Executive to any conflict of interest with respect
to Executive’s duties to the Company; and (iv) serve, with the written approval of the Board, as a director of one or more
private or public companies, in each case so long as any such activities do not significantly interfere with the performance of
Executive’s responsibilities under this Agreement, create a conflict of interest, or create an adverse interest or position
detrimental to Company.

     

     

    

 

(c)        Policies.
Executive shall faithfully adhere to, execute, and fulfill all lawful policies established by the Company as are communicated
to Executive by the Company.

(d)        Place
of Performance. In connection with Executive’s employment by the Company, Executive shall be based at the Company’s
principal executive offices in Boca Raton, Florida.

2.          
Compensation. For all services rendered by Executive, the Company shall compensate Executive as follows:

(a)        Base
Salary. Effective on the Effective Date, the base salary (“Base Salary”) payable to Executive shall be
Four hundred twenty thousand dollars ($420,000) per year, payable on a regular basis in accordance with the Company’s standard
payroll procedures, but not less than monthly. The Board or a committee of the Board shall review Executive’s performance
on at least an annual basis and may make increases to such Base Salary if, in its sole discretion, any such increase is warranted.
The Board may reduce the Base Salary without Executive’s consent only if such reduction applies in the same or greater percentage
to all other executives of the Company at the Chief level and above.

(b)        Annual
Short-Term Incentive. Executive shall be entitled to participate in the Company’s annual short-term incentive compensation
program, as such program may exist from time to time, at a level commensurate with that being offered to other executives of the
Company at the Chief level and above. For calendar years beginning on or after January 1, 2020, the percentage of Base Salary
targeted as annual cash short-term incentive compensation for each calendar year during the Term shall be seventy-five percent
(75%) of Base Salary (the “Targeted Annual Bonus Award”). Executive acknowledges that the amount of annual
short-term incentive compensation, if any, to be awarded shall be at the sole, good faith discretion of the Board or a committee
of the Board, may be less or more than the Targeted Annual Bonus Award, and will be based on a number of factors determined by
the Board or a committee of the Board for each calendar year, including the Company’s performance in connection with, among
other factors, the clinical program, regulatory filings, commercialization and/or sales, and Executive’s individual performance.
Any annual short-term incentive compensation earned for any calendar year shall be paid in the immediately following calendar
year, as soon as practicable. Except as set forth in Sections 3(b)(ii), 3(b)(iii), and 3(b)(iv) hereof.
Executive must be employed by the Company on the date on which short-term incentive compensation is paid in order to receive such
short-term incentive compensation. Executive’s 2020 bonus will not be prorated due to a mid-year start.

    2

     

    

(c)            Long-Term
Incentive.   Executive shall be entitled to participate in the Company’s
long-term incentive compensation program, as such program may exist from time to time, at a level commensurate with that being
offered to other executives of the Company at the Chief level and above. Executive acknowledges that the amount of long-term incentive
compensation, if any, to be awarded shall be at the sole, good faith discretion of the Board or a committee of the Board, and
will be based on a number of factors determined by the Board or a committee of the Board for the applicable performance period,
including the Company’s performance in connection with, among other factors, the clinical program, regulatory filings, commercialization
and/or sales, and Executive’s individual performance. Any long-term incentive compensation earned for the applicable performance
period shall be paid within the first two-and-a-half (21⁄2) months of the calendar year immediately following the calendar
year in which the applicable performance period ends. Except as otherwise set forth herein, Executive must be employed by the
Company on the date on which long-term incentive compensation is paid to receive such long-term incentive compensation.

(d)            Restricted Stock Units. As
soon as practicable following the Effective Date and subject to approval by the Board of Directors, the Company will grant to
Executive six hundred fifty-one thousand five hundred (651,500) restricted stock units (“RSUs”) pursuant to
the Company’s 2019 Stock Incentive Plan, as the same may be amended from time to time (the “Plan”), which
RSUs will vest in equal amounts annually over (3) years from the Effective Date, one-third vesting on each of June 1, 2021, June
1, 2022, and June 1, 2023, subject to Executive’ continued employment with the Company and the terms and conditions in the
Plan and an award agreement to be entered into between the Company and Executive. Executive will also be granted 151,500 performance
share units (“PSUs”) that will vest if the Company achieves EBITDA breakeven, provided EBITDA breakeven is accomplished
on or before December 31, 2022.

(e)            Executive
Perquisites, Benefits, and Other Compensation. Executive shall be entitled to receive additional benefits and compensation
from the Company in such form and to such extent as specified below:

(i)      
Insurance Coverage. During the Term, and as otherwise provided within the provisions of each of the respective plans, the
Company shall make available to Executive all employee benefits to which other executives of the Company are entitled to receive,
subject to the eligibility requirements and other provisions of such arrangements as applicable to executives of the Company generally.
Such benefits shall include, but shall not be limited to, comprehensive health and major medical insurance, dental and life insurance,
and short-term and long-term disability. The Company will provide to Executive D&O insurance and other insurance coverage
typically provided to in-house legal counsel, including legal liability coverage, as reasonably necessary.

(ii)      Reimbursement
for Expenses. Reimbursement for business travel and other out-of-pocket expenses reasonably incurred by Executive in the performance
of Executive’s services under this Agreement, which shall be paid as paid for other executives of the Company at the Chief
level and above., including, but not limited to, industry appropriate seminars and subscriptions and applicable licensing and
continuing education expenses. All reimbursable expenses shall be appropriately documented in reasonable detail by Executive upon
submission of any request for reimbursement and shall be in a format and manner consistent with the Company’s expense reporting
policy. Reimbursements under this section shall be paid within sixty (60) days following date of submission.

    3

     

    

(iii)     Paid
Time Off. Executive shall be eligible to accrue PTO and utilize and carryover from year to year such PTO, consistent with
the Company’s policies and procedures in effect from time to time for executives of the Company at the Chief level and above.

(iv)      Other
Executive Perquisites. The Company shall provide Executive with other executive perquisites as may be made available to or
deemed appropriate for Executive by the Board or a committee of the Board and participation in all other Company-wide employee
benefits as are available to the Company’s executives from time to time, including any plans, programs, or arrangements
relating to retirement, deferred compensation, profit sharing, 401(k), and employee stock ownership.

(v)       Working
Facilities. During the Term, the Company shall furnish Executive with an office, staffing and administrative support and such
other facilities and services suitable to Executive’s position with the Company and adequate for the performance of Executive’s
duties hereunder, which will be reviewed and provided based on the Company’s needs.

(vi)     Commute Expenses and Relocation. The
Company will reimburse Executive for his reasonable expenses with respect to his temporary housing or hotel, rental vehicle, and
airfare to commute from his home to Boca Raton, Florida for a reasonable, mutually agreed upon period of time not to exceed two
(2) years from the Effective Date. The Company will reimburse Executive for his reasonable expenses with respect to relocating
his home to the Boca Raton, Florida area. Reimbursements under this section shall be paid within sixty (60) days following date
of submission and in a manner consistent with the Company’s policies and procedures in effect from time to time for executives
of the Company at the Chief level and above.

3.      
     Term of Employment.

(a)           Termination Under Certain Circumstances.

(i)      
Death. Executive’s
employment and the Term shall be automatically terminated, without notice, effective upon the date of Executive’s death.

(ii)      Disability.
If, as a result of incapacity due to physical or mental illness or injury, Executive shall have been absent from Executive’s
full-time duties hereunder for six (6) consecutive months, then thirty (30) days after giving written notice to Executive (which
notice may occur before or after the end of such six (6) month period, but which shall not be effective earlier than the last
day of such six (6) month period), the Company may terminate Executive’s employment and the Term, provided Executive is
unable to resume Executive’s full-time duties at the conclusion of such notice period.

    4

     

    

(iii)          Termination by the Company for Good Cause.
The Company may terminate Executive’s employment and the Term upon ten (10) days prior written notice to Executive for “Good
Cause,” which shall mean any one or more of the following: (A) Executive’s material breach of this Agreement (continuing
for thirty (30) days after receipt of written notice of need to cure, if, in the Company’s determination, such breach is
curable); (B) Executive’s negligence in the performance or intentional nonperformance (continuing for thirty (30) days after
receipt of written notice of need to cure, if, in the Company’s determination, such breach is curable) of any of Executive’s
material duties and responsibilities; (C) Executive’s willful dishonesty, fraud, or misconduct with respect to the business
or affairs of the Company; (D) Executive’s indictment for, charge of, conviction of, or guilty or nolo contendre
plea to a felony crime involving dishonesty or moral turpitude whether or not relating to the Company; (E) a confirmed positive
drug test result for an illegal drug; or (F) a material sanction is imposed on Executive by any applicable professional organization
or professional governing body including, for the avoidance of doubt, an accounting regulatory board.

(iv)          Termination by the Company Without Good Cause.
The Company may terminate Executive’s employment and the Term at any time without Good Cause. A termination by Executive
without Good Reason shall not be a breach of this Agreement by Executive.

(v)           Termination by Executive Without Good Reason.
Executive, at Executive’s option and upon written notice to the Company, may terminate Executive’s employment and
the Term without Good Reason (as defined below) at any time, effective on the date of that notice.

(vi)          Termination by Executive With Good Reason.
At any time during the Term, Executive may terminate Executive’s employment and the Term for Good Reason. For purposes of
this Agreement, “Good Reason” shall mean (A) the assignment to Executive of material duties inconsistent with
Executive’s position as the Chief Financial Officer (including status, office, titles and reporting requirements), or any
other action by the Company that results in a material diminution in such position, excluding for this purpose (i) any action
not taken in bad faith and that is remedied by the Company promptly after receipt of a Notice of Termination for Good Reason (as
defined below) thereof given by Executive and (ii) any change in status, office, titles and reporting requirements following a
Change in Control of the Company in which the Company ceases to be a standalone public reporting company, provided that the material
duties of Executive following such Change in Control are not inconsistent with those of Executive immediately prior to such Change
in Control; (B) the Company requiring Executive to be based at any office or location other than in Palm Beach County, Florida,
or within thirty-five (35) miles of such location, or such other location as mutually agreed to by the Company and Executive,
except for travel reasonably required in the performance of Executive’s responsibilities, provided, however, that this clause
3(iv)(B) will not have any force or effect until such time that and only for the period of time that Executive has permanently
relocated his home and permanently resides within thirty-five (35) miles of the Company’s Boca Raton headquarters; or (C)
any material failure by the Company to comply with any of the provisions of this Agreement, other than a failure not occurring
in bad faith and that is remedied by the Company promptly after receipt of a Notice of Termination for Good Reason given thereof
by Executive. A termination of employment by Executive for Good Reason shall be effected by Executive’s giving the Board
written notice (“Notice of Termination for Good Reason”) of the termination, setting forth in reasonable detail
the specific conduct of the Company that constitutes Good Reason and the specific provision(s) of this Agreement on which Executive
relies, within ninety (90) days of the initial existence of one of the conditions constituting Good Reason. A termination of employment
by Executive for Good Reason shall be effective on the thirty-first (31st) day following the date when the Notice of Termination
for Good Reason is given to the Company; provided that such a termination of employment shall not become effective if the Company
shall have substantially corrected the circumstance giving rise to the Notice of Termination for Good Reason within thirty (30)
days after the Company’s receipt of such Notice of Termination for Good Reason.

    5

     

    

(b)        Result
of Termination.

(i)      
Except as otherwise set forth in this Agreement, in the event of the termination of Executive’s employment and the Term
pursuant to Sections 3(a)(iii) (“Termination by the Company for Good Cause”) or 3(a)(v) (“Termination
by Executive Without Good Reason”) hereof, Executive shall receive no further compensation under this Agreement
other than the payment of Base Salary as shall have accrued and remained unpaid as of the date of termination, unreimbursed business
expenses, and accrued but unused PTO consistent with the Company’s policies and procedures therefor in effect at the time
of such termination for officers of Executive’s level.

(ii)       In the event of the termination of Executive’s employment and the Term pursuant to Sections 3(a)(iv) (“Termination
by the Company Without Good Cause”) or 3(a)(vi) (“Termination by Executive With Good Reason”)
hereof, (a) Executive shall, for a period of twelve (12) months following the effective date of such termination, continue to
receive Executive’s then current annual Base Salary, as provided in Section 2(a), (b) Executive shall receive
an amount equal to Executive’s Targeted Annual Bonus Award for the calendar year in which the termination of Executive’s
employment occurs, which amount shall be paid to Executive in a single lump sum, which is unpaid on the effective date of Executive’s
termination, and which shall be paid to Executive when paid to other similarly situated executives of the Company in accordance
with Section 2(b) hereof, (c) Executive shall receive, beginning on the first payroll date occurring on or after the thirtieth
(30th) day following the effective date of the termination of Executive’s employment under this Agreement and
for a period of twenty-four (24) months thereafter for a total of twenty-four (24) monthly payments, a monthly cash payment equal
to the one (1) month cost of COBRA continuation of the health insurance benefits for Executive and Executive’s immediate
family as applicable, as the effective date of such termination, less, the one (1) month cost for the same health insurance benefits
for Executive and Executive’s immediate family as applicable that would have been incurred by Executive immediately prior
to the effective date of such termination if Executive remained employed with the Company, (d) all unvested equity compensation
of any kind (including, without limitation, stock options, restricted stock, RSUs, performance shares or PSUs) held by Executive
in Executive’s capacity as an employee of the Company on the effective date of the termination shall vest as of the effective
date of such termination, (e) Executive shall receive payment for (1) Base Salary as shall have accrued and remained unpaid as
of the date of termination, (2) unreimbursed business expenses, (3) accrued but unused PTO consistent with the Company’s
policies and procedures therefor in effect at the time of such termination for executives of the Company at the Chief level and
above, and (4) any annual short-term incentive compensation earned pursuant to Section 2(b) hereof for the calendar year immediately
preceding the calendar year in which the termination of Executive’s employment occurs which is unpaid on the effective date
of Executive’s termination, which shall be paid to Executive when paid to other similarly situated executives of the Company
in accordance with Section 2(b) hereof (the preceding clauses (e)(1), (e)(2), (e)(3) and (e)(4) collectively, the “Accrued
Compensation”).

    6

     

    

(iii)      In the event of the termination of Executive’s employment and the Term pursuant to Sections 3(a)(i) (“Death”)
or 3(a)(ii) (“Disability”) hereof, (a) Executive shall receive an amount equal to Executive’s
Targeted Annual Bonus Award for the calendar year in which the termination of Executive’s employment occurs, multiplied
by a fraction, the numerator of which is the number of full months of such calendar year during which Executive was employed with
the Company, and the denominator of which is twelve (12), which amount shall be paid to Executive in a single lump sum on the
first payroll date occurring on or after the thirtieth (30th) day following the effective date of the termination of
Executive’s employment under this Agreement, (b) all unvested equity compensation of any kind (including, without limitation,
stock options, restricted stock, RSUs, performance shares or PSUs) held by Executive in Executive’s capacity as an employee
of the Company on the effective date of the termination shall vest as of the effective date of such termination, (c) Executive
shall receive payment for the Accrued Compensation.

(iv)      In the event of the termination of Executive’s employment and the Term pursuant to Sections 3(a)(iv) (“Termination
by the Company Without Good Cause”) or 3(a)(vi) (“Termination by Executive With Good Reason”)
hereof during the twelve (12) month period immediately following a Change in Control or otherwise in connection with such Change
in Control, then in lieu of any benefits or amounts otherwise payable under Section 3(b)(ii) hereof, (a) Executive shall,
for a period of eighteen (18) months following the effective date of such termination, continue to receive Executive’s then
current annual Base Salary, as provided in Section 2(a), (b) Executive shall receive an amount equal to one and one
half times (1.5x) Executive’s Targeted Annual Bonus Award for the calendar year in which the termination of Executive’s
employment occurs, which amount shall be paid to Executive in a single lump sum on the first payroll date occurring on or after
the thirtieth (30th) day following the effective date of the termination of Executive’s employment under this
Agreement, (c) Executive shall receive, beginning on the first payroll date occurring on or after the thirtieth (30th)
day following the effective date of the termination of Executive’s employment under this Agreement and for a period of eighteen
(18) months thereafter for a total of eighteen (18) monthly payments, a monthly cash payment equal to the one (1) month cost of
COBRA continuation of the health insurance benefits for Executive and Executive’s immediate family as applicable, as the
effective date of such termination, less, the one (1) month cost for the same health insurance benefits for Executive and Executive’s
immediate family as applicable that would have been incurred by Executive immediately prior to the effective date of such termination
if Executive remained employed with the Company, (d) all unvested equity compensation of any kind (including, without limitation,
stock options, restricted stock, RSUs, performance shares or PSUs) held by Executive in Executive’s capacity as an employee
of the Company on the effective date of the termination shall vest as of the effective date of such termination, (e) Executive
shall receive payment for the Accrued Compensation.

    7

     

    

(c)         Release. Notwithstanding
any other provision in this Agreement to the contrary, as a condition precedent to receiving any post-termination payments or
benefits identified in Sections 3(b)(ii), 3(b)(iii) and 3(b)(iv) hereof, Executive agrees to execute
(and not revoke) a full and complete release of all claims against the Company and its affiliates, in the form attached hereto
as Exhibit A (subject to such modifications as the Company reasonably may request) (the “Release”). If Executive
fails to execute and deliver to the Company the Release within twenty-one (21) days following the date of termination, or revokes
the Release, within seven (7) days following the date Executive executes and delivers the Release, or materially breaches any
term of this Agreement or any other agreement between Executive and the Company while receiving such post-termination payments
or benefits, Executive agrees that Executive shall not be entitled to receive any such post-termination payments. For purposes
of this Agreement, the Release shall be deemed to have been executed by Executive if it is signed by Executive’s legal representative
in the case of legal incompetence or on behalf of Executive’s estate in the case of Executive’s death. Payment of
any post-termination payments or benefits identified in Sections 3(b)(ii), 3(b)(iii) and 3(b)(iv) hereof
shall be delayed until the first payroll date occurring on or after the thirtieth (30th) day following the effective
date of the termination of Executive’s employment under this Agreement, and any payments that are so delayed shall be paid
on the first payroll date occurring on or after the thirtieth (30th) day following the effective date of the termination
of Executive’s employment under this Agreement.

(d)         Section 409A.
Any payments made by the Company pursuant to Sections 3(b)(ii), 3(b)(iii) and 3(b)(iv) hereof (except
for unpaid annual short-term incentive compensation earned in the calendar year immediately preceding the calendar year in which
the termination of Executive’s employment occurs, which shall be paid to Executive when paid to other similarly situated
executives of the Company) shall be paid or commence on the first payroll date occurring on or after the thirtieth (30th)
day following the effective date of Executive’s “separation from service” within the meaning of Section 409A
(“Section 409A”) of the Internal Revenue Code of 1986, as amended (the “Code”). For purposes
of applying the provisions of Section 409A to this Agreement, each separately identified amount to which Executive is entitled
under this Agreement shall be treated as a separate payment. In addition, to the extent permissible under Section 409A, any series
of installment payments under this Agreement shall be treated as a right to a series of separate payments. Executive shall receive
no additional compensation following any termination except as provided herein. In the event of any termination, Executive shall
resign all positions with the Company and its subsidiaries. If Executive is a “specified employee” within the meaning
of Section 409A, then payments identified in Section 3(b) of this Agreement shall not commence until six (6) months following
“separation from service” within the meaning of Section 409A to the extent necessary to avoid the imposition of the
additional twenty percent (20%) tax under Section 409A (and in the case of installment payments, the first payment shall include
all installment payments required by this subsection that otherwise would have been made during such six-month period). If the
payments described in Section 3(b) are “deferred compensation” within the meaning of Section 409A and
must be delayed for six (6) months pursuant to the preceding sentence, Executive shall not be entitled to additional compensation
to compensate for such delay period. Upon the date such payment would otherwise commence, the Company shall reimburse Executive
for such payments, to the extent that such payments otherwise would have been paid by the Company had such payments commenced
upon Executive’s “separation from service” within the meaning of Section 409A. Any remaining payments shall
be provided by the Company in accordance with the schedule and procedures specified herein. This Agreement is intended to satisfy
the requirements of Section 409A with respect to amounts subject thereto, and shall be interpreted and construed consistent with
such intent. Any reimbursements by the Company to Executive of any eligible expenses under this Agreement that are not excludable
from Executive’s income for Federal income tax purposes (the “Taxable Reimbursements”) shall be made
by no later than the last day of the taxable year of Executive following the year in which the expense was incurred. The amount
of any Taxable Reimbursements, and the value of any in-kind benefits to be provided to Executive, during any taxable year of Executive
shall not affect the expenses eligible for reimbursement, or in-kind benefits to be provided, in any other taxable year of Executive.
The right to Taxable Reimbursement, or in-kind benefits, shall not be subject to liquidation or exchange for another benefit.
Notwithstanding the foregoing, the Company does not make any representation to Executive that the payments or benefits provided
under this Agreement are exempt from, or satisfy, the requirements of Section 409A, and the Company shall have no liability or
other obligation to indemnify or hold harmless Executive or any beneficiary for any tax, additional tax, interest or penalties
that Executive or any beneficiary may incur in the event that any provision of this Agreement, or any amendment or modification
thereof, or any other action taken with respect thereto, is deemed to violate any of the requirements of Section 409A.

    8

     

    

(e)       Section
280G. 

(i)      
Certain Reductions in Agreement Payments.
Anything in this Agreement to the contrary notwithstanding, in the event a nationally recognized independent accounting firm designated
by the Company and reasonably acceptable to Executive (the “Accounting Firm”) shall determine that receipt
of all payments or distributions by the Company and its affiliates in the nature of compensation to or for Executive’s benefit,
whether paid or payable pursuant to this Agreement or otherwise (a “Payment”), would subject Executive to the
excise tax under Section 4999 of the Code, the Accounting Firm shall determine as required below in this Section 3(e) whether
to reduce any of the Payments paid or payable pursuant to this Agreement (the “Agreement Payments”) to the
Reduced Amount (as defined below). The Agreement Payments shall be reduced to the Reduced Amount only if the Accounting Firm determines
that Executive would have a greater Net After-Tax Receipt (as defined below) of aggregate Payments if Executive’s Agreement
Payments were so reduced. If the Accounting Firm determines that Executive would not have a greater Net After-Tax Receipt of aggregate
Payments if Executive’s Agreement Payments were so reduced, then Executive shall receive all Agreement Payments to which
Executive is entitled. 

(ii)       Accounting
Firm Determinations. If the Accounting Firm determines that aggregate Agreement Payments should be reduced to the Reduced
Amount, then the Company shall promptly give Executive notice to that effect and a copy of the detailed calculation thereof. All
determinations made by the Accounting Firm under this Section 3(e) shall be binding upon the Company and Executive and
shall be made as soon as reasonably practicable and in no event later than twenty (20) days following the effective date of the
termination of Executive’s employment with the Company. For purposes of reducing the Agreement Payments to the Reduced Amount,
only amounts payable under this Agreement (and no other Payments) shall be reduced. The reduction of the amounts payable hereunder,
if applicable, shall be made (A) only from Payments that the Accounting Firm determines reasonably may be characterized as “parachute
payments” under Section 280G of the Code; (B) only from Payments that are required to be made in cash, (C) only with respect
to any amounts that are not payable pursuant to a “nonqualified deferred compensation plan” subject to Section 409A
of the Code, until those payments have been reduced to zero, and (D) in reverse chronological order, to the extent that any Payments
subject to reduction are made over time (e.g., in installments). In no event, however, shall any Payments be reduced if and to
the extent such reduction would cause a violation of Section 409A of the Code or other applicable law. All fees and expenses of
the Accounting Firm shall be borne solely by the Company.

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(iii)       Overpayments; Underpayments. As a result of the uncertainty in the application of Section 4999 of the Code at the time
of the initial determination by the Accounting Firm hereunder, it is possible that amounts will have been paid or distributed
by the Company to or for the benefit of Executive pursuant to this Agreement which should not have been so paid or distributed
(an “Overpayment”) or that additional amounts which will have not been paid or distributed by the Company to
or for the benefit of Executive pursuant to this Agreement which should have been so paid or distributed (an “Underpayment”),
in each case consistent with the calculation of the Reduced Amount hereunder. In the event that the Accounting Firm, based upon
the assertion of a deficiency by the Internal Revenue Service against either the Company or Executive which the Accounting Firm
believes has a high probability of success determines that an Overpayment has been made, Executive shall pay any such Overpayment
to the Company together with interest at the applicable federal rate provided for in Section 7872(f)(2) of the Code; provided,
however, that no amount shall be payable by Executive to the Company if and to the extent such payment would not either
reduce the amount on which Executive is subject to tax under Section 1 and Section 4999 of the Code or generate a refund
of such taxes. In the event that the Accounting Firm, based upon controlling precedent or other substantial authority, determines
that an Underpayment has occurred, any such Underpayment shall be paid promptly (and in no event later than 60 days following
the date on which the Underpayment is determined) by the Company to or for the benefit of Executive together with interest at
the applicable federal rate provided for in Section 7872(f)(2) of the Code.

(iv)       Definitions. The following terms shall have the following meanings for purposes of this Section 3:

(A)         “Net After-Tax Receipt” shall mean the present value (as determined in accordance with Sections 280G(b)(2)(A)(ii)
and 280G(d)(4) of the Code) of a Payment net of all taxes imposed on Executive with respect thereto under Sections 1 and 4999
of the Code and under applicable state and local laws, determined by applying the highest marginal rate under Section 1 of the
Code and under state and local laws which applied to Executive’s taxable income for the immediately preceding taxable year,
or such other rate(s) as the Accounting Firm determined to be likely to apply to Executive in the relevant taxable year(s).

(B)          “Reduced
Amount” shall mean the greatest amount of Agreement Payments that can be paid that would not result in the imposition
of the excise tax under Section 4999 of the Code if the Accounting Firm determines to reduce Agreement Payments pursuant to Section
3(e)(i) hereof.

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4.           Competition
and Non-Solicitation.

(a)         Interests
to be Protected. The parties acknowledge that Executive will perform essential services for the Company, its employees, and
its stockholders during the term of Executive’s employment with the Company. Executive will be exposed to, have access to,
and work with, a considerable amount of confidential information. The parties also expressly recognize and acknowledge that the
personnel of the Company have been trained by, and are valuable to, the Company and that the Company will incur substantial recruiting
and training expenses if the Company must hire new personnel or retrain existing personnel to fill vacancies. The parties expressly
recognize that it could seriously impair the goodwill and diminish the value of the Company’s business should Executive
compete with the Company in any manner whatsoever. The parties acknowledge that this covenant has an extended duration; however,
they agree that this covenant is reasonable and it is necessary for the protection of the Company, its stockholders, and employees.
For these and other reasons, and the fact that there are many other employment opportunities available to Executive if Executive’s
employment is terminated, the parties are in full and complete agreement that the following restrictive covenants are fair and
reasonable and are entered into freely, voluntarily, and knowingly. Furthermore, each party was given the opportunity to consult
with independent legal counsel before entering into this Agreement.

(b)         Non-Competition.
During the term of Executive’s employment with the Company and for eighteen (18) months after the termination of Executive’s
employment with the Company, which may be extended an additional twelve (12) months in the sole and absolute discretion of the
Company for a total of thirty (30) months after termination of Executive’s employment with the Company, regardless of the
reason therefor, Executive shall not (whether directly or indirectly, as owner, principal, agent, stockholder, director, officer,
manager, employee, partner, participant, or in any other capacity) engage or become substantially and directly financially interested
in any Competitive Business Activities conducted within the Restricted Territory (as defined below). In the event of the termination
of Executive’s employment and the Term pursuant to Sections 3(a)(iv) (“Termination by the Company Without
Good Cause”) or 3(a)(vi) (“Termination by Executive With Good Reason”) hereof, if the
Company exercises its right to extend this non-competition clause by the additional twelve (12) months, then Executive will, (a)
for a period of twelve (12) additional months, continue to receive Executive’s then current annual Base Salary, as provided
in Section 2(a) hereof, and (b) Executive will receive for a period of an additional six (6), a monthly cash payment
equal to the one (1) month cost of COBRA continuation of the health insurance benefits for Executive and Executive’s immediate
family as applicable. As used herein, the term “Competitive Business Activities” shall mean business activities
that are competitive with the business of the Company, including but not limited to, business activities in the pharmaceutical
industry related to products that compete with the Company’s products, and the term “Restricted Territory”
shall mean any state or other geographical area in which the Company has demonstrated an intent to develop, commercialize, and/or
distribute products during Executive’s employment with the Company. Executive hereby agrees that, as of the date hereof,
during Executive’s employment with the Company, the Company has demonstrated an intent to develop, commercialize, and/or
distribute products throughout the United States of America, Canada, Mexico, Brazil, Argentina, Europe, Australia, South Africa,
Russia, Israel, Japan, and South Korea.

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(c)          Non-Solicitation
of Employees. During the term of Executive’s employment and for a period of twenty-four (24) months after the termination
of Executive’s employment with the Company, regardless of the reason therefor, Executive shall not directly or indirectly,
for the Company, or on behalf of or in conjunction with any other person, company, partnership, corporation, or governmental or
other entity, solicit for employment, seek to hire, or hire any person who is employed by the Company, is a consultant of the
Company, or is an independent contractor of the Company, within twenty-four (24) months of the termination of Executive’s
employment, and, as related solely to consultants, for the purpose of having any such consultant engage in services that are the
same as, similar to, or related to the services that such consultant provided for the Company and that are competitive with the
services provided by the consultant for the Company.

(d)          Non-Solicitation
of Customers. During the term of Executive’s employment and for a period of twenty-four (24) months after the termination
of Executive’s employment with the Company, regardless of the reason therefor, Executive shall not directly or indirectly,
for the Company, or on behalf of, or in conjunction with, any other person, company, partnership, corporation, or governmental
entity, call on, solicit, or engage in business with, any of the actual or targeted prospective customers or clients of the Company
on behalf of any person or entity in connection with any Competitive Business, nor shall Executive make known the names and addresses
of such actual or targeted prospective customers or clients, or any information relating in any manner to the trade or business
relationships of the Company with such customers or clients, other than in connection with the performance of Executive’s
duties under this Agreement, and/or persuade or encourage or attempt to persuade or encourage any persons or entities with whom
the Company does business or has some business relationship to cease doing business or to terminate its business relationship
with the Company or to engage in any Competitive Business Activities on its own or with any competitor of the Company. As used
herein, the term “Competitive Business” shall mean business that is directly competitive with the business
of the Company, including but not limited to, business in the pharmaceutical industry related to products that directly compete
with the Company’s products.

(e)          Employee Assignment, Invention and Confidentiality
Agreement. Executive hereby affirms, acknowledges, and agrees that Executive will be subject
to the terms and conditions set forth in that certain Employee Assignment, Invention, and Confidentiality Agreement (the “EAICA”)
by and between the Company and Executive and that this Agreement does not modify or amend the EAICA. 

(f)           Equitable
Relief. In the event a violation of any of the restrictions contained in this Section 4 occurs, the Company shall
be entitled to seek from a court of competent jurisdiction preliminary and permanent injunctive relief (without being required
to post bond), reasonable attorneys’ fees, and damages and an equitable accounting of all earnings, profits, and other benefits
arising from such violation, which right shall be cumulative and in addition to any other rights or remedies to which the Company
may be entitled. In the event of a violation of any provision of Section 4(b), Section 4(c), or Section
4(d) hereof, the period for which those provisions would remain in effect shall be extended for a period of time equal to
that period beginning when such violation commenced and ending when the activities constituting such violation shall have been
finally terminated in good faith.

    12

     

    

(g)          Restrictions
Separable. If the scope of any provision of this Agreement (whether in this Section 4 or otherwise) is found by
a court of competent jurisdiction to be too broad to permit enforcement to its full extent, then such provision shall be enforced
to the maximum extent permitted by law. The parties agree that the scope of any provision of this Agreement may be modified by
a judge in any proceeding to enforce this Agreement, so that such provision can be enforced to the maximum extent permitted by
law. Each and every restriction set forth in this Section 4 is independent and severable from the others, and no such
restriction shall be rendered unenforceable by virtue of the fact that, for any reason, any other or others of them may be unenforceable
in whole or in part.

5.         
Return of Company Property. At any time as requested by the Company, or upon the termination of Executive’s employment
with the Company for any reason, Executive shall deliver promptly to the Company all files, lists, books, records, manuals, memoranda,
drawings, and specifications; all other written or printed materials and computers, cell phones, and other equipment that are
the property of the Company (and any copies of them); and all other materials that may contain confidential information relating
to the business of the Company, which Executive may then have in Executive’s possession or control, whether prepared by
Executive or not.

6.         
Cooperation. Following the Term, Executive shall give assistance and cooperation willingly, upon reasonable advance notice
with due consideration for Executive’s other business or personal commitments, in any matter relating to Executive’s
position with the Company, or Executive’s expertise or experience as the Company may reasonably request, including Executive’s
attendance and truthful testimony where deemed appropriate by the Company, with respect to any investigation or the Company’s
defense or prosecution of any existing or future claims or litigations or other proceedings relating to matters in which Executive
was involved or potentially had knowledge by virtue of Executive’s employment with the Company. The Company agrees that
(a) it shall promptly reimburse Executive for Executive’s reasonable and documented expenses in connection with rendering
assistance and/or cooperation under this Section 6 upon Executive’s presentation of documentation for such expenses
and (b) Executive shall be reasonably compensated for his continued material services as required under this Section 6.
The parties agree to negotiate the reasonable compensation reference in 6(b) in good faith.

7.           
No Prior Agreements. Executive hereby represents and warrants to the Company that the execution of this Agreement by Executive
and Executive’s employment by the Company and the performance of Executive’s duties hereunder will not violate or
be a breach of any agreement with a former employer, client, or any other person or entity. Further, Executive agrees to indemnify
the Company for any claim, including, but not limited to, attorneys’ fees and expenses of investigation, by any such third
party that such third party may now have or may hereafter come to have against the Company based upon or arising out of any non-competition,
invention, or secrecy agreement between Executive and such third party that was in existence as of the date of this Agreement.

    13

     

    

 

8.           
Miscellaneous.

(a)           Notice.
All notices, requests, demands, and other communications required or permitted under this Agreement shall be in writing and shall
be deemed to have been duly given, made, and received (i) if personally delivered, on the date of delivery, (ii) if by e-mail
transmission, upon receipt, (iii) if mailed United States mail, registered or certified, return receipt requested, postage prepaid,
and addressed as provided below, upon receipt or refusal of delivery, or (iv) if by a courier delivery service providing overnight
or “next-day” delivery, upon receipt or refusal of delivery, in each case addressed as follows: 

	  To the Company:	TherapeuticsMD, Inc.
	 	951
Yamato Road, Suite 220

Boca
Raton, Florida 33431

Attention:
Chief Executive Officer

Phone:
(561) 961-1900

	 	 
	  With a copy, which shall not constitute notice, to:
	 	 
	 	TherapeuticsMD,
Inc.

951
Yamato Road, Suite 220

Boca
Raton, Florida 33431

Attention:
General Counsel

Phone:
(561) 961-1900

  

	  To Executive:	James C. D’Arecca

 

	  With a copy to:	Stewart Reifler, Esq.
	 	8
Brightfield Lane

Westport,
Connecticut 06880

Phone:
(203) 557-0722

	 	 

Either
party may alter the address to which communications or copies are to be sent by giving notice of such change of address in conformity
with the provisions of this Section 8 for the giving of notice.

(b)           Indulgences;
Waivers. Neither any failure nor any delay on the part of either party to exercise any right, remedy, power, or privilege
under this Agreement shall operate as a waiver thereof, nor shall any single or partial exercise of any right, remedy, power,
or privilege preclude any other or further exercise of the same or of any other right, remedy, power, or privilege, nor shall
any waiver of any right, remedy, power, or privilege with respect to any occurrence be construed as a waiver of such right, remedy,
power, or privilege with respect to any other occurrence. No waiver shall be binding unless executed in writing by the party making
the waiver.

(c)           Controlling
Law. This Agreement and all questions relating to its validity, interpretation, performance and enforcement, shall be governed
by and construed in accordance with the laws of the State of Florida, notwithstanding any Florida or other conflict-of-interest
provisions to the contrary, unless superseded by federal law. Venue for any action arising out of this Agreement or the employment
relationship shall be brought only in courts of competent jurisdiction in or for Palm Beach County, Florida and each party hereby
irrevocably waives, to the fullest extent permitted by law, any objection which they may now or hereafter have to the laying of
venue in such courts and submits to the jurisdiction of such courts. THE PARTIES (BY THEIR ACCEPTANCE HEREOF) HEREBY KNOWINGLY,
IRREVOCABLY, VOLUNTARILY, AND INTENTIONALLY WAIVE ANY RIGHT EACH MAY HAVE TO A TRIAL BY JURY WITH RESPECT TO ANY DISPUTES BASED
UPON OR ARISING OUT OF THIS AGREEMENT.

    14

     

    

(d)           Execution
in Counterpart. This Agreement may be executed in any number of counterparts, each of which shall be deemed to be an original
as against any party whose signature appears thereon, and all of which shall together constitute one and the same instrument.
This Agreement shall become binding when one or more counterparts hereof, individually or taken together, shall bear the signatures
of the parties reflected hereon as the signatories.

(e)           Entire Agreement.
Except as herein contained, this Agreement contains the entire understanding between the parties hereto with respect to the subject
matter hereof and supersedes all prior and contemporaneous agreements and understandings, inducements, and conditions, express
or implied, oral or written, which shall no longer have any force or effect. The express terms hereof control and supersede any
course of performance and/or usage of the trade inconsistent with any of the terms hereof. This Agreement may not be modified
or amended other than by an agreement in writing signed by Executive and an authorized representative with actual authority to
bind Company.

(f)            Controlling Document.
If any provision of any agreement, plan, program, policy, arrangement or other written document between or relating to the Company
and Executive conflicts with any provision of this Agreement, the provision of this Agreement shall control and prevail.

(g)           Section Headings.
The section headings in this Agreement are for convenience only; they form no part of this Agreement and shall not affect its
interpretation.

(h)           Number of Days.
In computing the number of days for purposes of this Agreement, all days shall be counted, including Saturdays, Sundays, and holidays;
provided, however, that if the final day of any time period falls on a Saturday, Sunday, or holiday, then the final day shall
be deemed to be the next day that is not a Saturday, Sunday, or holiday.

(i)      
    Successors and Assigns. This
Agreement shall inure to the benefit of and be binding upon the successors and assigns of the parties hereto; provided that because
the obligations of Executive hereunder involve the performance of personal services, such obligations shall not be delegated by
Executive. For purposes of this Agreement, successors and assigns shall include, but not be limited to, any individual, corporation,
trust, partnership, or other entity that acquires a majority of the stock or assets of the Company by sale, merger, consolidation,
liquidation, or other form of transfer. The Company will require any successor (whether direct or indirect, by purchase, merger,
consolidation, or otherwise) to all or substantially all of the business and/or assets of the Company to expressly assume and
agree to perform this Agreement in the same manner and to the same extent that the Company would be required to perform it if
no such succession had taken place.

    15

     

    

(j)            Tax Withholding. The
Company may withhold from any benefits payable under this Agreement all federal, state, city, or other taxes as may be required
pursuant to any law or governmental regulation or ruling.

(k)           Survival. The
respective rights and obligations of the parties hereunder shall survive any termination of Executive’s employment hereunder,
including without limitation, the Company’s obligations under Section 3 hereof and Executive’s obligations under Section
4 hereof, and the expiration of the Term, to the extent necessary to the intended preservation of such rights and obligations.

(l)           
Right to Consult with Counsel; No Drafting Party.
Executive acknowledges having read and considered all of the provisions of this Agreement carefully,
and having had the opportunity to consult with counsel of Executive’s own choosing, and, given this, Executive agrees that
the obligations created hereby are not unreasonable. Executive acknowledges that Executive has had an opportunity to negotiate
any and all of these provisions and no rule of construction shall be used that would interpret any provision in favor of or against
a party on the basis of who drafted the Agreement.

[Signature
Page Follows]

    16

     

    

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

	 	THERAPEUTICSMD, INC.
	 	 
	 	/s/ Robert
    Finizio
	 	Robert Finizio
	 	Chief Executive Officer
	 	 
	 	EXECUTIVE:
	 	 
	 	/s/ James
    C. D’Arecca
	 	James C. D’Arecca

 

[Signature
Page to Employment Agreement] 

     

     

    

EXHIBIT
A

FORM OF SEPARATION AGREEMENT AND RELEASE

This
Separation Agreement (“Agreement”) is made between TherapeuticsMD, Inc. (“Company”) and ____________________
(“Employee”), intending to be legally bound, and in consideration of the mutual covenants contained herein, and other
valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties agree as follows:

 

1.      
Separation and Severance. Employee’s final day of employment with Company was ____________________. Although the
parties agree that Company does not owe Employee any further consideration, as severance if this release is not executed by Employee,
Company agrees to pay Employee as set forth in Employee’s Employment Agreement dated __________________ (the “Employment
Agreement”), provided Employee executes this Agreement, complies with its terms and the terms of Employee’s Employment
Agreement[[, and does not revoke this Agreement during the Revocation Period as defined in Section 8 below.]]1 Employee
acknowledges that no other compensation of any kind remains outstanding, that the consideration provided herein is more than Employee
would otherwise be entitled to receive, that Employee shall not be entitled to any other payments or benefits from Company, and
that no other amounts are due or owing or shall become due or owing relating to any obligation, agreement, or otherwise.

 

2.      
Execution of Separation Agreement. Should Employee wish to accept this Agreement, it must be signed and returned to ________________________________
by ______________.

 

3.      
EAICA. Employee acknowledges and agrees that Employee’s obligations contained in the paragraphs 2, 3, 4, 6, 8, 9,
10 and 11 of the Employee Assignment, Invention, and Confidentiality Agreement (“EAICA”) that Employee signed on _____________________,
a copy of which is attached as Exhibit A, remain in full force and effect. The terms of this Agreement are in additional to and
do not supersede the surviving terms of the EAICA.

 

4.      
Confidentiality of Agreement. Employee understands and agrees that the existence of this Agreement and the terms and conditions
thereof, shall be considered confidential, and shall not be disclosed by Employee to any third party or entity except with the
prior written approval of Company, to Employee’s spouse or attorney or financial advisor, or upon the order of a court of
competent jurisdiction. Notwithstanding anything in this Agreement to the contrary, nothing in this Agreement or any other agreement
between the Company and Employee shall prevent Employee from sharing information and communicating in good faith, without prior
notice to the Company, with any federal government agency having jurisdiction over the Company or its operations, and cooperating
in any investigation by any such federal government agency; provided that Employee receives no monies for compensatory or other
damages as a result of participating in any such communication or cooperation with the EEOC.

 

 

1
Employee will be entitled to a revocation period only if over the age of 40 at the date of termination.

 

    A-1 

     

    

 

5.      
Non-Disparagement. At all time Employee will refrain from and will not directly or indirectly engage in any conversation
that would tend to negatively impact Company or any of its subsidiaries or any of its past and current directors and senior executives.

 

6.      
Return of Company Property. Employee agrees to immediately return to Company any and all property of Company in Employee’s
possession, custody, or control. No severance shall be paid pursuant to this Agreement until all Company property is returned.

 

7.      
Confidential Information. Employee acknowledges that Employee has had access to Company confidential and proprietary information
and agrees that all such Confidential Information is and shall remain the exclusive property of Company. Employee further agrees
that Employee shall not publish, disclose, or otherwise make available to any third party any such Confidential Information, except
(i) as such disclosure or use may be or may have been required or appropriate in connection with his work as an employee of the
Company, (ii) when required to do so by a court of law, by any governmental agency having supervisory authority over the business
of the Company or by any administrative or legislative body (including a committee thereof) with apparent jurisdiction to order
him to divulge, disclose or make accessible such information, (iii) as to such Confidential Information that becomes generally
known to the public or trade without his violation of this Section 7 or (iv) to Employee’s spouse, attorney and/or his personal
tax and financial advisors as reasonably necessary or appropriate to advance Employee’s tax, financial and other personal
planning (each an “Exempt Person”), provided, however, that any disclosure or use of any Confidential Information
by an Exempt Person shall be deemed to be a breach of this Section 7 by Employee. Employee acknowledges and agrees that Employee
has continuing confidentiality obligations under the EAICA. Employee warrants that Employee has no materials containing Confidential
Information, but if Employee does, Employee shall return immediately to Company any and all materials containing any Confidential
Information in Employee’s possession, custody, or control. The terms of this Separation Agreement comprise confidential
information of the Company.

 

8.      
Release. That the undersigned, ________________, for good and valuable consideration, the receipt and sufficiency of which
are hereby acknowledged, intending to be legally bound, and Employee’s past, present and future agents, representatives,
attorneys, affiliates, heirs, executors, assigns and successors, and all other persons connected therewith, and on behalf of all
successors and assigns, hereby releases and forever discharges TherapeuticsMD, Inc., vitaMedMD, LLC, BocaGreenMD, Inc., vitaCare
Prescription Services and all of their past, present and future agents, representatives, principals, attorneys, affiliates, owners,
parent corporations, subsidiaries, officers, directors, employees, assigns and successors, and all other persons, firms or corporations
connected or affiliated therewith (collectively “Releasees”), of and from any and all legal, equitable or other claims,
demands, setoffs, defenses, contracts, accounts, suits, debts, agreements, actions, causes of action, sums of money, judgments,
findings, controversies, disputes, or past, present and future duties, responsibilities, obligations, or suits at law and/or equity
of whatsoever kind, from the beginning of the world to the date hereof, in addition, without limitation, any and all actions,
causes of action, claims, counterclaims, third party claims, and any and all other federal, state, local and/or municipality statutes,
laws and/or regulations and any ordinance and/or common law pertaining to employment or otherwise and any and all other claims
which have been or which could have been asserted against any party in any forum.

 

    A-2 

     

    

 

By
signing this Agreement, Employee knowingly and voluntarily fully releases and forever discharges Releasees of and from all claims,
demands and liability of any kind arising under any statute, law or ordinance, including, without limitation, Title VII of the
Civil Rights Act of 1964, the Fair Labor Standards Act, the National Labor Relations Act, the Americans with Disabilities Act,
any state Human Rights Act, Fla. Stat. 448, or any facts or claims arising under the Age Discrimination in Employment Act (“ADEA”).
This release is intended to cover all actions, causes of action, claims and demands for damages, loss or injury arising from the
beginning of time until the date of this Agreement, whether presently known or unknown to Employee. However, Employee does not
waive Employee’s rights to claims which may arise after this Agreement becomes effective.

 

In
addition, Employee is hereby advised to consult with an attorney prior to executing this Agreement. Employee agrees that Employee
has been given a reasonable time in which to consider the Agreement and seek such consultation. Employee further warrants that
Employee has consulted with knowledgeable persons concerning the effect of this Agreement and all rights which Employee might
have under any and all state and federal laws relating to employment and employment discrimination and otherwise. Employee fully
understands these rights and that by signing this Agreement Employee forfeits all rights to sue Releasees for matters relating
to or arising out of employment, separation, or otherwise.

 

In
accordance with provisions of the ADEA, as amended, 29 U.S.C. §601-634, Employee is hereby provided a period of twenty-one
(21) days from the date Employee receives this Agreement to review the waiver of rights under the ADEA and sign this Agreement.
Furthermore, Employee has seven (7) days after the date Employee signs the Agreement (“Revocation Period”) to revoke
Employee’s consent. This Agreement shall not become effective or enforceable until the Revocation Period has expired. If
Employee does not deliver a written revocation to ___________________________ before the Revocation Period expires, this Agreement
will become effective.

 

Notwithstanding
anything in this Section 8 to the contrary, releases contained in this Agreement shall not apply to (i) any rights to receive
any payments or benefits pursuant to Sections 3(b)(ii), 3(b)(iii) or 3(b)(iv) of the Employment Agreement, (ii) any rights or
claims that may arise as a result of events occurring after the date this Agreement is executed, (iii) any indemnification rights
Employee may have as a former officer or director of the Company or its subsidiaries or affiliated companies, (iv) any claims
for benefits under any directors’ and officers’ liability policy maintained by the Company or its subsidiaries or
affiliated companies in accordance with the terms of such policy, (v) any claims for vested benefits under any Company pension
benefit plan or welfare benefit plan in which Employee and his dependents participate, and/or (vi) any rights as a holder of equity
securities of the Company.

 

9.      
Opportunity to Seek Counsel. The parties represent that they have had an opportunity to retain legal counsel to represent
them in connection with this matter, that they have been advised of the legal effect and consequences of this Agreement, that
they have entered into this Agreement knowingly, freely and voluntarily of their own volition, and that they have not been coerced,
forced, harassed, threatened or otherwise unduly pressured to enter into this Agreement.

 

    A-3 

     

    

10.     Reporting of Known Issues. As a further condition to your receipt of the benefits described in this Agreement, you hereby
represent and warrant that you have reported in writing to ___________________________ any unethical conduct or violations of
laws, regulations, Company policies and procedures by the Company, a Company employee, or a Company officer of which you are aware.

 

11.     No Admissions. This Agreement is not and shall not in any way be construed as an admission by either party of any wrongful
act or omission, or any liability due and owing, or any violation of any federal, state or local law or regulation.

 

12.     Miscellaneous. This Agreement may not be amended or modified except in writing signed by Employee and an authorized representative
with actual authority to bind Company, specifically stating that it is an amendment to this Agreement. This Agreement shall be
governed by and construed in accordance with Sections 4(g) (Restrictions Separable), 8(a) (Notice), 8(b) (Indulgences;
Waivers), 8(c) (Controlling Law), 8(d) (Execution in Counterpart), 8(f) (Section Headings), and 8(k)
(Right to Consult with Counsel; No Drafting Party) of the Employment Agreement. This Agreement and the Employment Agreement
constitute the entire Agreement between the parties hereto with respect to the subject matter hereof; provided, however, that
Employee’s continuing obligations to the Company under the terms of the EAICA are incorporated herein and shall remain in
full force and effect as set forth herein.

 

IN
WITNESS THEREOF, the parties hereto acknowledge, understand and agree to this Agreement and intend to be bound by all of the clauses
contained in this document.

	 	 	 	 	 	 
	EMPLOYEE	 	THERAPEUTICSMD, INC.
	 	 	 	 	 	 
	 	 	 	By:	 	 
	[Employee]	 	 	 	 
	 	 	 	Its:	 	 
	 	 	 	 	 	 
	Date: 	 	 	Date:	 	 
	 	 	 	 	 	 

 

    A-4

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