Oteseconazole Chemical Properties

Boiling point:

609.2±65.0 °C(Predicted)

Density 

1.47±0.1 g/cm3(Predicted)

vapor pressure 

0-0Pa at 20-50℃

storage temp. 

Store at -20°C

solubility 

DMSO: ≥ 270 mg/mL (511.96 mM)

form 

Solid

pka

10.49±0.29(Predicted)

color 

White to off-white

LogP

4.41 at 45℃ and pH0-14

Oteseconazole Usage And Synthesis

Description

Oteseconazole (trade name Vivjoa) is an antifungal drug that was approved by the United States Food and Drug Administration (USFDA) in April 2022 for the treatment of recurrent vaginal candidiasis in women who have a history of recurrent vaginal candidiasis and are not of reproductive potential.

Uses

Oteseconazole (Standard) is the analytical standard of Oteseconazole. This product is intended for research and analytical applications. Oteseconazole (VT-1161) is a potent and orally active anti-fungal agent. Oteseconazole potently binds to and inhibits Candida albicans cytochrome P45051 (CYP51) activity (Kd ≤39 nM), shows no obvious effect on human CYP51. Oteseconazole also can be used for the research of dermatophytes.

Definition

ChEBI: Oteseconazole is an organic molecular entity.

Mechanism of action

The antifungal activity of Oteseconazole has been attributed to its inhibition of ergosterol 14-alpha demethylase (CYP51), a cytochrome P450 enzyme involved in the biosynthesis of ergosterol, a component required for the maintenance of fungal cell membrane integrity.

Synthesis

To complete the synthesis of orticonazole, the resolved amino alcohol 5.8 was first subjected to salting out and then Suzuki coupling with boronic acid 5.9 to afford the biaryl product 5.10 as the L-tartrate salt. Conversion of 5.10 to orticonazole was accomplished using TMSN3 in acetic acid in the presence of sodium acetate and trimethoxyformate. The reaction solution was treated with a palladium adsorbent and subsequently recrystallized from ethanol and water after adjusting the pH with potassium carbonate. Oteseconazole was isolated in hydrated form in 85% yield.