Stockholders' Equity | 10. Stockholders’ Equity Authorized, Issued, and Outstanding Common Shares The Company’s authorized common stock has a par value of $ 0.001 per share and consists of 150,000,000 shares as of December 31, 2022 and 100,000,000 shares as of December 31, 2021; 32,682,342 and 28,705,334 shares were issued and outstanding at December 31, 2022 and 2021, respectively. In September 2022, the Company amended its Amended and Restated Certificate of Incorporation to increase the total number of authorized shares of common stock from 100,000,000 to 150,000,000 . Shares Reserved for Future Issuance The Company had reserved shares of common stock for future issuance as follows: December 31, 2022 2021 Outstanding stock options 1,740,308 1,542,126 Outstanding restricted stock units 633,270 133,834 Warrants to purchase common stock associated with March 2018 public offering - Series 2 798,810 798,810 Warrants to purchase common stock associated with December 2020 public offering - Series 2 6,800,000 6,800,000 Prefunded warrants to purchase common stock associated with December 2020 public offering 3,200,000 3,200,000 Warrants to purchase common stock associated with April 2022 Public Offering 15,000,000 — Prefunded warrants to purchase common stock associated with April 2022 Public Offering 11,666,667 — Warrants to purchase common stock associated with Loan Agreement 198,811 170,410 Warrants to purchase common stock associated with Danforth 50,000 50,000 For possible future issuance for the conversion of the March 2019 Notes 1,138,200 1,138,200 For possible future issuance under 2014 Plan (Note 13) 712,020 295,220 For possible future issuance under employee stock purchase plan — 3,893 For possible future issuance under 2015 Plan (Note 13) 550,964 235,000 Total common shares reserved for future issuance 42,489,050 14,367,493 Liquidation Rights In the event of any liquidation or dissolution of the Company, the holders of the common stock are entitled to the remaining assets of the Company legally available for distribution. Dividends and Voting Rights The holders of the common stock are entitled to receive dividends if and when declared by the Company. Preferred Stock On May 7, 2014, the Company amended and restated its articles of incorporation relating to its approved capital structure. The Company’s board of directors has authorized the Company, subject to limitations prescribed by Delaware law, to issue up to 5,000,000 shares of preferred stock with a par value of $ 0.001 per share in one or more series, to establish from time to time the number of shares to be included in each series and to fix the designation, powers, preferences and rights of the shares of each series and any of its qualifications, limitations or restrictions. The Company’s board of directors can also increase or decrease the number of shares of any series of preferred stock, but not below the number of shares of that series then outstanding, without any further vote or action by the stockholders. The Company’s board of directors may authorize the issuance of preferred stock with voting or conversion rights that could adversely affect the voting power or other rights of the holders of the common stock. There were no shares of preferred stock issued and outstanding as of December 31, 2022 and 2021. Common Stock Purchase Agreement and Sales Agreements On April 10, 2020, the Company entered into the Common Stock Purchase Agreement with Aspire Capital (the “Common Stock Purchase Agreement”) pursuant to which the Company had the right to sell to Aspire Capital from time to time in its sole discretion up to $ 20.0 million in shares of the Company’s common stock, subject to certain limitations and conditions set forth in the Common Stock Purchase Agreement. The Common Stock Purchase Agreement expired in October 2022. During the years ended December 31, 2022 and 2021, the Company sold 425,000 and 400,000 shares of its common stock under the Common Stock Purchase Agreement for gross proceeds of $ 1.6 million and $ 2.6 million, respectively. During the years ended December 31, 2022, and 2021, the Company sold 137,610 and 494,406 shares of its common stock and received net proceeds of $ 0.7 million and $ 3.1 million, respectively, under the Controlled Equity OfferingSM Sales Agreements with Cantor Fitzgerald & Co. and Ladenburg Thalmann & Co. Inc. (the “Sales Agreements”). April 2022 Public Offering On April 22, 2022, the Company entered into an Equity Underwriting Agreement (the “Underwriting Agreement”) with Guggenheim Securities, LLC, as representative of the several underwriters (the “Underwriters”), relating to the offering, issuance and sale (the “April 2022 Public Offering”) of (a) 3,333,333 shares of the Company’s common stock, par value $ 0.001 per share, (b) prefunded warrants, in lieu of common stock, to purchase 11,666,667 shares of the Company’s common stock, par value $ 0.001 per share, and (c) warrants, which will accompany the common stock or prefunded warrants, to purchase up to an aggregate of 15,000,000 shares of the Company’s common stock. The prefunded warrants entitle the holders to purchase up to 11,666,667 shares of common stock and have an unlimited term and an exercise price of $ 0.001 per share. The warrants entitle the holders to purchase up to an aggregate of 15,000,000 shares of common stock and have a seven-year term and an exercise price of $ 3.45 per share. The warrants that accompany the prefunded warrants have an additional provision entitling the holder thereof to purchase a prefunded warrant rather than a share of common stock at the warrant exercise price less the exercise price of the prefunded warrant purchased. Each warrant is exercisable immediately upon issuance, subject to certain limitations on beneficial ownership. The price to the public in the April 2022 Public Offering was $ 3.00 per share of common stock and accompanying warrants, or in the case of prefunded warrants, $ 2.999 per prefunded warrant and accompanying warrants, which resulted in $ 41.8 million of net proceeds to the Company after deducting the underwriting discount and offering expenses. The prefunded warrants are classified as equity in accordance with ASC 815, Derivatives and Hedging , given the prefunded warrants are indexed to the Company’s own shares of common stock and meet the requirements to be classified in equity. The prefunded warrants were recorded at their relative fair value at issuance in the stockholders’ equity section of the balance sheet and the prefunded warrants are considered outstanding shares in the basic earnings per share calculation for the year ended December 31, 2022 given their nominal exercise price. December 2020 Public Offering Warrants On December 17, 2020, the Company completed a public offering (the “December 2020 Public Offering”) of its common stock and warrants pursuant to the Company’s effective shelf registration. The Company sold an aggregate of (a) 8,340,000 shares of the Company’s common stock, par value $ 0.001 per share, (b) prefunded warrants, in lieu of common stock, to purchase 5,260,000 shares of the Company’s common stock, par value $ 0.001 per share, and (c) two series of warrants, which will accompany the common stock or prefunded warrants, to purchase up to an aggregate of 13,600,000 shares of the Company’s common stock. The prefunded warrants entitle the holders to purchase up to 5,260,000 shares of common stock and have an unlimited term and an exercise price of $ 0.001 per share. During the year ended December 31, 2021, 2,060,000 of the prefunded warrants were exercised for proceeds of $ 2,000 . Each of the two series of warrants entitle the holders to purchase up to an aggregate of 6,800,000 shares of common stock. The prefunded warrants are classified as equity in accordance with ASC 815, Derivatives and Hedging , given the prefunded warrants are indexed to the Company’s own shares of common stock and meet the requirements to be classified in equity. The prefunded warrants were recorded at their relative fair value at issuance in the stockholders’ equity section of the balance sheet and the prefunded warrants are considered outstanding shares in the basic earnings per share calculation for the years ended December 31, 2022 and 2021 given their nominal exercise price. The Series 1 warrants had a one-year term and an exercise price of $ 7.33 per share, and the Series 2 warrants have a three-and-a-half-year term and an exercise price of $ 8.25 per share. There is not expected to be any trading market for the prefunded warrants, the Series 1 warrants, or the Series 2 warrants issued in the offering. Each warrant is exercisable immediately upon issuance, subject to certain limitations on beneficial ownership. The Series 1 and Series 2 warrants that accompany the prefunded warrants have an additional provision, if certain beneficial ownership limitations are met, entitling the holder thereof to purchase a prefunded warrant rather than a share of common stock at the warrant exercise price less the exercise price of the prefunded warrant purchased. The price to the public in the offering was $ 6.25 per share of common stock and accompanying warrants, or in the case of prefunded warrants, $ 6.249 per prefunded warrant and accompanying warrants. In June 2021, 360,134 of the December 2020 Series 1 public offering warrants were exercised for proceeds of $ 2.6 million. On December 21, 2021, the Board of Directors approved a modified exercise price of $ 6.25 per common share for up to 6,100,000 of the Series 1 warrants. 5,980,800 of the Series 1 warrants were repriced at $ 6.25 per common share and 3,370,800 were exercised for gross proceeds of $ 21.1 million which was received by the Company in December 2021. Of the 3,370,800 warrants exercised by the warrant holders, 2,390,000 warrants were held by 5 % beneficial owners of the Company for gross proceeds of $ 14.9 million. The 3,370,800 Series 1 warrants were ultimately fair valued with the resulting change in fair value recognized in earnings. The resulting fair value of the 3,370,800 was $ 1.9 million and the Company recognized the change in fair value in earnings of $ 1.4 million. On the settlement date, the contractual liability value of $ 1.9 million for the 3,370,800 Series 1 warrants was derecognized and included in additional paid in capital as part of the settlement. The remaining Series 1 warrants expired unexercised on December 21, 2021 and the remaining liability balance was derecognized. On November 24, 2021, an investor provided a conversion notice of 160,000 shares for gross proceeds to the Company of $ 1.2 million which was received in November 2021. As a result, the 160,000 Series 1 warrants were fair valued with the resulting change in fair value recognized in earnings. The resulting fair value of the 160,000 Series 1 warrants was $ 0.1 million and the Company recognized the change in fair value in earnings of $ 0.1 million. On the settlement date, the contractual liability value of $ 0.1 million for the 160,000 Series 1 warrants was derecognized and included in additional paid in capital as part of the settlement. December 2019 Public Offering Warrants On December 12, 2019, the Company completed a public offering (the “December 2019 Public Offering”) of its common stock and warrants pursuant to the Company's effective Shelf Registration. The Company sold an aggregate of 3,888,888 shares of the Company’s common stock and warrants to purchase up to an aggregate of 3,888,888 shares of the Company’s common stock at a public offering price of $ 9.00 per share and accompanying warrant. Net proceeds from the December 2019 Public Offering were approximately $ 32.5 million, after deducting the underwriting discount and offering expenses. The warrants to purchase shares of common stock are immediately exercisable and expire on the earlier of (i) such date that is six months after the Company publicly announces the approval from the U.S. Food and Drug Administration for ibrexafungerp for the treatment of vulvovaginal candidiasis and (ii) June 12, 2023 , and have an exercise price of $ 11.0 per share. There is not expected to be any trading market for the warrants. Each warrant is exercisable immediately upon issuance, subject to certain limitations on beneficial ownership. On November 26, 2021, the Board of Directors approved a modified exercise price of $ 6.50 per common share for 1,111,111 of the warrants issued to a 5 % beneficial owner and investor of the Company and no other terms of the original warrant were modified. On November 30, 2021, the investor provided a notice to exercise 1,111,111 of 2019 Warrants for proceeds of $ 7.2 million which was received by the Company on December 1, 2021. On the settlement date, the contractual liability value of $ 0.2 million for the 1,111,111 warrants was derecognized and included in additional paid in capital as part of the settlement. Additionally, on December 2, 2021, the Board of Directors also approved a reduced exercise price of $ 6.50 per common share for 361,111 , 827,777 , 194,444 , and 111,111 of the warrants issued to certain investors. On December 2, 2021, one investor provided a notice to exercise 111,111 of the warrants for proceeds of $ 0.7 million which was received by the Company in December 2021. As a result, the 111,111 warrants were fair valued on December 2, 2021 with the resulting change in fair value recognized in earnings. The resulting fair value of the 111,111 warrants was $ 19,000 and the Company recognized the change in fair value in earnings of $ 18,000 . On the settlement date, the contractual liability value of $ 19,000 for the 111,111 warrants was derecognized and included in additional paid in capital as part of the settlement. The remaining 2019 Warrants expired unexercised (including the 2019 Warrants that had a revised exercise price that went unexercised) on December 2, 2021 and the remaining liability balance was derecognized. March 2018 Public Offering Warrants On March 8, 2018, the Company completed a public offering (the “March 2018 Public Offering”) of its common stock and warrants pursuant to the Company’s effective shelf registration. The Company sold an aggregate of 1,775,150 shares of the Company’s common stock and warrants to purchase up to 2,130,180 shares of the Company’s common stock at a public offering price of $ 16.90 per share. Each purchaser received a warrant to purchase 0.75 of a share of common stock (the “March 2018 Series 1 warrants”) and 0.45 of a share of common stock (the “March 2018 Series 2 warrants”) for each share purchased in the March 2018 Public Offering. The March 2018 Series 1 warrants to purchase in the aggregate up to 1,331,370 shares of common stock had a 53 -week term and an exercise price of $ 18.5 per share, and the March 2018 Series 2 warrants to purchase in the aggregate up to 798,810 shares of common stock have a five-year term and an exercise price of $ 20.0 per share. There is not expected to be any market for the warrants and each warrant is exercisable immediately upon issuance, subject to certain limitations on beneficial ownership. Public Offering Warrant Liabilities The March 2018, December 2019, and December 2020 warrants contain a provision where the warrant holder has the option to receive cash, equal to the Black-Scholes fair value of the remaining unexercised portion of the warrant, as cash settlement in the event that there is a fundamental transaction (contractually defined to include various merger, acquisition or stock transfer activities). Due to this provision, ASC 480, Distinguishing Liabilities from Equity , requires that these warrants be classified as liabilities. The fair values of these warrants have been determined using the Black-Scholes valuation model, and the changes in the fair value are recorded in the accompanying consolidated statements of operations. The outstanding warrants associated with the April 2022 Public Offering meet the definition of a derivative pursuant to ASC 815, Derivatives and Hedging , and do not meet the derivative scope exception given the warrants do not qualify under the indexation guidance. As a result, the April 2022 Public Offering warrants were initially recognized as liabilities and measured at fair value using the Black-Scholes valuation model. During the years ended December 31, 2022 and 2021, the Company recorded gains of $ 22.3 million and $ 30.4 million , respectively, due to the change in fair value of the warrant liabilities. Issuance costs of $ 1.7 million initially allocated to the April 2022 Public Offering warrant liabilities were written off upon settlement and were recognized in the gain on the fair value adjustment for the warrant liabilities for the year ended December 31, 2022. As of December 31, 2022, the fair value of the warrant liabilities was $ 18.6 million. Warrant Associated with Danforth Advisors Pursuant to a consulting agreement with Danforth Advisors (“Danforth”) entered into in November 2021, the Company issued to Danforth a warrant to purchase 50,000 shares of the Company’s common stock at an exercise price of $ 5.50 per share. The warrant will expire five years from the date of the grant and will vest ratably over 24 months from the date of grant. The warrant was classified as equity and was initially fair valued using the Black-Scholes model on the grant date. In accordance with ASC 718, the Company recognized consulting expense for the non-employee share-based payment over the period the Company received Danforth’s services. |