U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of OTESECONAZOLE

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
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Interscience Conference on Antimicrobial Agents and Chemotherapy - 50th Annual Meeting - Research on Promising New Agents: Part 2.
2010 Nov
The clinical candidate VT-1161 is a highly potent inhibitor of Candida albicans CYP51 but fails to bind the human enzyme.
2014 Dec
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
Patents

Sample Use Guides

Once daily for 7 days starting at Day 1, followed by once weekly for 11 weeks. (VT-1161 150mg capsule)
Route of Administration: Oral
Name Type Language
OTESECONAZOLE
INN   WHO-DD  
INN   USAN  
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
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CAS
1340593-59-0
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RXCUI
2602577
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NCI_THESAURUS
C170270
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PUBCHEM
77050711
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FDA UNII
VHH774W97N
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DAILYMED
VHH774W97N
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INN
10138
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DRUG BANK
DB13055
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SMS_ID
300000022313
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