In November 2020, we entered into an at-the-market offering program (the “2020 ATM Program”) relating to shares of our common stock. The 2020 ATM Program permitted us to offer and sell shares of our common stock having an aggregate offering price of up to $50.0 million from time to time through or to the sales agent under the 2020 ATM Program. Sales of our common stock were permitted to be made from time to time in at-the-market offerings as defined in Rule 415 of the Securities Act of 1933, as amended (the “Securities Act”), including by means of ordinary broker’s transactions on the Nasdaq Stock Exchange or otherwise at market

prices prevailing at the time of sale, at prices related to prevailing market prices, or as otherwise agreed to with the sales agent. The sales agent was entitled to compensation at a fixed commission rate of 3.0% of the aggregate gross sales price per share sold. As of February 8, 2021, sales of shares of our common stock under the 2020 ATM Program were completed when we sold an aggregate total of 28,600,689 shares of our common stock at an average sale price of $1.75 per share. For the 2020 ATM Program, we received net proceeds of $48.1 million, after deducting the discounts and commissions to the sales agent and estimated offering expenses.

In February 2021, we closed on an underwritten public offering of our common stock, pursuant to which we issued 59,459,460 shares of our common stock at an offering price of $1.85 per share, and we received net proceeds of $96.6 million, after deducting the underwriting discounts and commissions and estimated offering expenses.

In March 2021, we entered into an at-the-market equity offering program (the “2021 ATM Program”) relating to shares of our common stock. The 2021 ATM Program permits us to offer and sell shares of our common stock having an aggregate offering price of up to $100.0 million from time to time through or to the sales agent under the 2021 ATM Program. Sales of our common stock may be made from time to time in at-the-market offerings as defined in Rule 415 of the Securities Act, including by means of ordinary broker’s transactions on the Nasdaq Stock Exchange or otherwise at market prices prevailing at the time of sale, at prices related to prevailing market prices, or as otherwise agreed to with the sales agent. The sales agent will be entitled to compensation at a fixed commission rate of 3.0% of the aggregate gross sales price per share sold. The sales agent is not required to sell any specific number or dollar amounts of securities but will act as sales agent and use commercially reasonable efforts to sell on our behalf all of the shares of common stock requested to be sold by us, consistent with its normal trading and sales practices, on mutually agreed terms between us and the sales agent. Through September 30, 2021, we have sold a total of 33,705,315 shares of our common stock under the 2021 ATM Program at an average sale price of $1.21 per share and we received estimated net proceeds of $38.8 million, after deducting discounts and commissions to the sales agent and estimated offering expenses. Subsequently, through the date of this 10-Q Report, we have not sold any additional shares of our common stock under the 2021 ATM Program. Future sales, if any, under the 2021 ATM Program will depend on a variety of factors, including among others, market conditions, the trading price of our common stock, determinations by us of the appropriate sources of funding, and potential uses of funding available to us.

The following tables summarizes the status of our outstanding and exercisable warrants and related transactions since December 31, 2020 (in thousands, except weighed average exercise price and weighted average remaining contractual life data):

	Warrants outstanding and exercisable
	Warrants			Weighted Average Exercise Price		Aggregate Intrinsic Value		Weighted Average Remaining Contractual Life (in Years)
As of December 31, 2020		6,535		$	1.55	$	1,041		7.3
Exercised		(1,163	)		0.31
Expired		(245	)		4.80
As of September 30, 2021		5,127		$	1.52	$	-		8.6

The aggregate intrinsic value of warrants exercised during the nine months ended September 30, 2021 was $1.1 million.

At the 2021 annual meeting of stockholders of the Company, held on May 27, 2021, our stockholders among other things approved the First Amendment to the TherapeuticsMD, Inc. 2019 Stock Incentive Plan (the “2019 Plan”) to increase the number of shares of our common stock available under the 2019 Plan by 22,475,000 shares. As of September 30, 2021, there were 10,182,803 shares of common stock available for issuance under the 2019 Plan, consisting of (i) new shares, (ii) unallocated shares previously available for issuance under the 2012 Stock Incentive Plan (the “2012 Plan”) that were not then subject to outstanding “Awards” (as defined in the 2012 Plan), and (iii) unallocated shares previously available for issuance under the 2009 Long-Term Incentive Compensation Plan (the “2009 Plan” and together with the 2019 Plan and the 2012 Plan, the “Plans”) that were not then subject to outstanding “Awards” (as defined in the 2009 Plan). Any shares subject to outstanding options or other equity “Awards” under the 2019 Plan, the 2012 Plan and the 2009 Plan that are forfeited, expire or otherwise terminate without issuance of the underlying shares, or if any such Award is settled for cash or otherwise does not result in the issuance of all or a portion of the shares subject to such Award (other than shares tendered or withheld in connection with the exercise of an Award or the satisfaction of withholding tax liabilities), the shares to which

those Awards were subject, shall, to the extent of such forfeiture, expiration, termination, cash settlement or non-issuance, again be available for delivery with respect to Awards under the 2019 Plan. As of December 31, 2020, there were 2,583,565 shares of common stock available for issuance under the 2019 Plan.

In August 2021, the Company hired a new President and granted an “inducement grant” under Listing Rule 5635(c)(4) of The Nasdaq Stock Market LLC (“Nasdaq”) of 2,750,000 restricted stock units designated as “Time-Based Units” and 2,750,000 restricted stock units designated as “Performance Units” (the “August Inducement Grant”). The Time-Based Units and Performance Units were granted pursuant to certain Inducement Grant Restricted Stock Unit Agreement; accordingly, these equity awards were not counted against the shares of common stock available for issuance under the 2019 Plan.

At the 2021 annual meeting of stockholders of the Company, our stockholders approved an Offer to Exchange Eligible Options for New Restricted Stock Units (the “Exchange Offer”). The Exchange Offer allowed certain employee option holders, excluding the Company’s named executive officers, advisers, consultants, contractors, or present or past non-employee directors, to exchange some or all of their outstanding options to purchase shares of common stock that were granted before August 26, 2019, and had a per share exercise price equal to or greater than $5.01 (“Eligible Options”), for an award of restricted stock units of the Company (“New RSUs”), subject to specified conditions. In September 2021, following the expiration of the Exchange Offer, 69 eligible employees elected to exchange Eligible Options, and the Company accepted for cancellation Eligible Options to purchase an aggregate of 4,493,000 shares of common stock, representing approximately 91.5% of the total shares of common stock underlying the Eligible Options. Also, in September 2021, promptly following the expiration of the Exchange Offer, the Company granted 700,264 New RSUs in exchange for the cancellation of the tendered Eligible Options. The New RSUs vest in three equal annual installments beginning on September 29, 2022, subject to the terms and conditions of the 2019 Plan.

The following table summarizes the status of our outstanding and exercisable options and related transactions under the Plans, including the Exchange Offer, since December 31, 2020 (in thousands, except weighed average exercise price and weighted average remaining contractual life data):

	Options awards outstanding									Options awards exercisable
	Options Awards			Weighted Average Exercise Price		Aggregate Intrinsic Value		Weighted Average Remaining Contractual Life (in Years)		Options Awards		Weighted Average Exercise Price		Aggregate Intrinsic Value		Weighted Average Remaining Contractual Life (in Years)
As of December 31, 2020		23,782		$	4.80	$	152		5.2		19,863	$	5.06	$	117		4.6
Granted		60			1.21
Exercised		(61	)		0.40
Cancelled/Forfeited		(4,885	)		4.95
Expired		(483	)		5.59
As of September 30, 2021		18,413		$	4.40	$	21		4.2		17,228	$	4.53	$	21		3.9

The aggregate intrinsic value of options exercised during the nine months ended September 30, 2021 was less than $0.1 million.

The following table summarizes the status of our restricted stock units (“RSUs”) and related transactions, including the Exchange Offer and the August Inducement Grant since December 31, 2020 (in thousands, except weighed average grant date fair value):

	RSUs awards outstanding							RSUs awards vested and not settled
	RSUs			Weighted Average Grant Date Fair Value		Aggregate Intrinsic Value		RSUs		Weighted Average Grant Date Fair Value		Aggregate Intrinsic Value
As of December 31, 2020		7,061		$	1.76	$	8,544		—	$	—	$	—
Granted		11,684			1.09
Vested and settled		(2,034	)		1.17
Cancelled/Forfeited		(593	)		1.92
As of September 30, 2021		16,118		$	1.34	$	11,927		2,566	$	1.79	$	2,566

The aggregate intrinsic value of RSUs vested and settled during the nine months ended September 30, 2021 was $2.1 million.

The following table summarizes the status of our performance stock units (“PSUs”) and related transactions, including the August Inducement Grant since December 31, 2020 (in thousands, except weighed average grant date fair value):

	PSUs awards outstanding								PSUs awards vested and not settled
	PSUs				Weighted Average Grant Date Fair Value		Aggregate Intrinsic Value		PSUs		Weighted Average Grant Date Fair Value		Aggregate Intrinsic Value
As of December 31, 2020		2,404			$	1.08	$	2,909		—	$	—	$	—
Granted		7,337				1.05
Vested and settled		—				—
Cancelled/Forfeited		(72	)			1.07
As of September 30, 2021		9,669		⁽¹⁾	$	1.06	$	7,155		1,680	$	1.16	$	1,243

In June 2020, our stockholders approved the TherapeuticsMD, Inc. 2020 Employee Stock Purchase Plan (“ESPP”), which reserved 5,400,000 shares of our common stock for purchase by eligible employees. The ESPP permits eligible employees to purchase our common stock at a price per share which is equal to 85% of the lesser of (i) the fair market value of the shares on the offering date of the offering period or (ii) the fair market value of the shares on the purchase date. In May 2021, 150,078 shares were sold under the ESPP at an average sale price of $0.89 per share and we received proceeds of $0.1 million.

We recorded share-based compensation related to previously issued options, RSU and PSUs, as well as shares of common stock issued under the ESPP totaling $7.3 million and $3.1 million for the three months ended September 30, 2021 and 2020, respectively, and $12.8 million and $8.5 million for the nine months ended September 30, 2021 and 2020, respectively.

As of September 30, 2021, we had $22.7 million of unrecognized share-based compensation cost related to unvested options, RSUs and PSUs as well as shares issuable under the ESPP, which is included as additional paid-in capital in the accompanying consolidated balance sheets and may be adjusted for future changes in forfeitures.

The unrecognized share-based compensation cost as of September 30, 2021 is expected to be recognized as share-based compensation over a weighted average period of 2.2 years as follows (in thousands):