OTESECONAZOLE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H16F7N5O2
Molecular Weight	527.3943
Optical Activity	( + )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@@](CN1C=NN=N1)(C2=CC=C(F)C=C2F)C(F)(F)C3=NC=C(C=C3)C4=CC=C(OCC(F)(F)F)C=C4

InChI

InChIKey=IDUYJRXRDSPPRC-NRFANRHFSA-N

InChI=1S/C23H16F7N5O2/c24-16-4-7-18(19(25)9-16)21(36,11-35-13-32-33-34-35)23(29,30)20-8-3-15(10-31-20)14-1-5-17(6-2-14)37-12-22(26,27)28/h1-10,13,36H,11-12H2/t21-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H16F7N5O2
Molecular Weight	527.3943
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT03562156 | https://clinicaltrials.gov/ct2/show/NCT01891305 | https://clinicaltrials.gov/ct2/show/NCT02267356 |

Otesaconazole (previously known as VT-1161), an antifungal agent, is an oral inhibitor of fungal lanosterol demethylase (CYP51) but did not inhibit human CYP51. Inhibition of CYP51 results in the accumulation of chemicals known to be toxic to the fungus. CYP51 is the molecular target of the class of drugs referred to as 'azole antifungals'. Mycovia pharmaceuticals initiate enrolment in a phase III trial for the treatment of patients with recurrent vaginal candidiasis (yeast infection). In vitro and in vivo pharmacology studies have demonstrated that the drug is highly active against dermatophytes that cause onychomycosis. Viamet successfully completed phase II clinical trials were was studied the efficacy and safety of oral otesaconazole in patients with onychomycosis of the toenail. In addition, Viamet has completed phase II clinical trial, where was studied the efficacy and safety of otesaconazole in patients with moderate-severe interdigital tinea pedis.

Originator

Approval Year

PubMed

Title	Date	PubMed
Interscience Conference on Antimicrobial Agents and Chemotherapy - 50th Annual Meeting - Research on Promising New Agents: Part 2.	2010 Nov	21046516
The clinical candidate VT-1161 is a highly potent inhibitor of Candida albicans CYP51 but fails to bind the human enzyme.	2014 Dec	25224009
Structural analyses of Candida albicans sterol 14α-demethylase complexed with azole drugs address the molecular basis of azole-mediated inhibition of fungal sterol biosynthesis.	2017 Apr 21	28258218

Patents

Sample Use Guides

In Vivo Use Guide

Once daily for 7 days starting at Day 1, followed by once weekly for 11 weeks. (VT-1161 150mg capsule)

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:49:17 GMT 2023` Edited by `admin` on `Sat Dec 16 01:49:17 GMT 2023`
Record UNII	VHH774W97N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OTESECONAZOLE

Official Name

English

oteseconazole [INN]

Common Name

English

(R)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1H-tetrazol-1-yl)-1-(5-(4-(2,2,2-trifluoroethoxy)phenyl)pyridin-2-yl)propan-2-ol

Systematic Name

English

VT-1161

Code

English

OTESECONAZOLE, (+)-

Common Name

English

2-Pyridineethanol, α-(2,4-difluorophenyl)-β,β-difluoro-α-(1H-tetrazol-1-ylmethyl)-5-[4-(2,2,2-trifluoroethoxy)phenyl]-, (αR)-

Systematic Name

English

(αR)-α-(2,4-Difluorophenyl)-β,β-difluoro-α-(1H-tetrazol-1-ylmethyl)-5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridineethanol

Systematic Name

English

OTESECONAZOLE [USAN]

Common Name

English

Oteseconazole [WHO-DD]

Common Name

English

VIVJOA

Brand Name

English

Code System Code Type Description

USAN

HI-55