237,745 shares of our Series B Preferred Stock were issued in connection with a registered direct offering on December 18, 2020 (the “December 2020 Registered Direct Offering”). Each share of Series B Preferred Stock is convertible at any time at the option of the holder thereof, into one third (1/3) share of common stock, subject to a 9.99% blocker provision, and is subject to adjustment for stock splits, stock dividends, distributions, subdivisions and combinations.
As of December 31, 2023, 119,000 shares of the Series B Preferred Stock remained issued and outstanding. The 119,000 shares of Series B Preferred Stock issued and outstanding at December 31, 2023, are convertible into 39,667 shares of common stock.
In the event of a liquidation, the holders of Series B Preferred Shares are entitled to participate on an as-converted-to-common stock basis with holders of the common stock in any distribution of our assets to the holders of the common stock. The Series B Certificate of Designation provides, among other things, that we shall not pay any dividends on shares of common stock (other than dividends in the form of common stock) unless and until such time as we pay dividends on each Series B Preferred Share on an as-converted basis. Other than as set forth in the previous sentence, the Series B Certificate of Designation provides that no other dividends shall be paid on Series B Preferred Shares and that we shall pay no dividends (other than dividends in the form of common stock) on shares of common stock unless we simultaneously comply with the previous sentence.
With certain exceptions, as described in the Series B Certificate of Designation, the Series B Preferred Stock has no voting rights. However, as long as any shares of Series B Preferred Stock remain outstanding, the Series B Certificate of Designation provides that we shall not, without the affirmative vote of holders of a majority of the then-outstanding Series B Preferred Stock, (a) alter or change adversely the powers, preferences or rights given to the Series B Preferred Stock or alter or amend the Series B Certificate of Designation, (b) amend our certificate of incorporation or other charter documents in any manner that adversely affects any rights given to the holders of the Series B Preferred Stock, (c) increase the number of authorized shares of Series B Preferred Stock, or (d) enter into any agreement with respect to any of the foregoing.
Each share of Series B Preferred Stock is convertible at any time at the holder’s option into five shares of common stock. The “Series B Conversion Price” was initially $61.95 and is subject to adjustment for stock splits, stock dividends, distributions, subdivisions and combinations. Notwithstanding the foregoing, the Series B Certificate of Designation further provides that we shall not effect any conversion of Series B Preferred Stock, with certain exceptions, to the extent that, after giving effect to an attempted conversion, the holder of Series B Preferred Shares (together with such holder’s affiliates, and any persons acting as a group together with such holder or any of such holder’s affiliates) would beneficially own a number of shares of common stock in excess of 9.99% of the shares of our common stock then outstanding after giving effect to such exercise.
Warrants
As of December 31, 2023, there were 635,550 warrants outstanding. 24,968 warrants were outstanding as 2017 Warrants, 146,000 warrants were outstanding as April 2020 Warrants, 44,667 were outstanding as December 2020 Warrants and 419,925 were outstanding as December 2023 Warrants.
The 2017 Warrants have an exercise price of $600.00 per share and were issued in connection with the July 2017 Underwritten Public Offering and are immediately exercisable. The 2017 Warrants expire in 2024. Out of the April 2020 Warrants, 2,090,000 warrants are pre-funded warrants and have an exercise price of $0.001 per share and may be exercised at any time until exercised in full. The remaining 266,667 April 2020 Warrants are common stock warrants carrying an exercise price of $75.00 per share and an expiration date in 2025. The December 2020 Warrants have an exercise price of $61.95 per share and were issued in connection with the December 2020 Registered Direct Offering. The 2020 Warrants expire in 2025. The December 2023 Warrants have an exercise price of $3.19 per share (or $4.14375 per share for placement agent warrants) and were issued in connection with the December 2023 Registered Direct Offering. The 2023 Warrants expire in 2030 (or 2028 for placement agent warrants).
Subject to limited exceptions, a holder of warrants will not have the right to exercise any portion of its warrants if the holder (together with such holder’s affiliates, and any persons acting as a group together with such holder or any of such holder’s affiliates) would beneficially own a number of shares of common stock in excess of 4.99% (or, at