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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

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

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
The clinical candidate VT-1161 is a highly potent inhibitor of Candida albicans CYP51 but fails to bind the human enzyme.
2014 Dec
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
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
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
Created by admin on Sat Dec 16 01:49:17 GMT 2023 , Edited by admin on Sat Dec 16 01:49:17 GMT 2023
PRIMARY
CAS
1340593-59-0
Created by admin on Sat Dec 16 01:49:17 GMT 2023 , Edited by admin on Sat Dec 16 01:49:17 GMT 2023
PRIMARY
RXCUI
2602577
Created by admin on Sat Dec 16 01:49:17 GMT 2023 , Edited by admin on Sat Dec 16 01:49:17 GMT 2023
PRIMARY
NCI_THESAURUS
C170270
Created by admin on Sat Dec 16 01:49:17 GMT 2023 , Edited by admin on Sat Dec 16 01:49:17 GMT 2023
PRIMARY
PUBCHEM
77050711
Created by admin on Sat Dec 16 01:49:17 GMT 2023 , Edited by admin on Sat Dec 16 01:49:17 GMT 2023
PRIMARY
FDA UNII
VHH774W97N
Created by admin on Sat Dec 16 01:49:17 GMT 2023 , Edited by admin on Sat Dec 16 01:49:17 GMT 2023
PRIMARY
DAILYMED
VHH774W97N
Created by admin on Sat Dec 16 01:49:17 GMT 2023 , Edited by admin on Sat Dec 16 01:49:17 GMT 2023
PRIMARY
INN
10138
Created by admin on Sat Dec 16 01:49:17 GMT 2023 , Edited by admin on Sat Dec 16 01:49:17 GMT 2023
PRIMARY
DRUG BANK
DB13055
Created by admin on Sat Dec 16 01:49:17 GMT 2023 , Edited by admin on Sat Dec 16 01:49:17 GMT 2023
PRIMARY
SMS_ID
300000022313
Created by admin on Sat Dec 16 01:49:17 GMT 2023 , Edited by admin on Sat Dec 16 01:49:17 GMT 2023
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> INDUCER
mRNA levels in at least 2 hepatocyte cultures. Up 10 micromolar OTESECONAZOLE
METABOLIC ENZYME -> INHIBITOR
REVERSIBLE
IC50
TARGET ORGANISM->INHIBITOR
METABOLIC ENZYME -> INDUCER
mRNA levels in at least 2 hepatocyte cultures. Up 10 micromolar OTESECONAZOLE
METABOLIC ENZYME -> INHIBITOR
REVERSIBLE
IC50
BINDER->LIGAND
BINDING
OFF-TARGET->INHIBITOR
Cloned hERG Potassium Channels Expressed in Human Embryonic Kidney Cells
IC50
EXCRETED UNCHANGED
URINE
METABOLIC ENZYME -> INHIBITOR
Measured by midazolam 1′-hydroxylation; 42% inhibition at 10 micromolar.
IC50
METABOLIC ENZYME -> NON-INHIBITOR
METABOLIC ENZYME -> INDUCER
mRNA levels in at least 2 hepatocyte cultures. Up 10 micromolar OTESECONAZOLE
TARGET ORGANISM->INHIBITOR
TARGET ORGANISM->INHIBITOR
EXCRETED UNCHANGED
FECAL
METABOLIC ENZYME -> INDUCER
mRNA levels in at least 2 hepatocyte cultures. Up 10 micromolar OTESECONAZOLE
TARGET ORGANISM->INHIBITOR
TRANSPORTER -> INHIBITOR
Not clinically relevant in DDI study.
IC50
METABOLIC ENZYME -> INHIBITOR
REVERSIBLE
IC50
TRANSPORTER -> INHIBITOR
Clinically relevant in DDI study resulted in a clinically significant increase in rosuvastatin exposure.
IC50
TARGET ORGANISM->INHIBITOR
METABOLIC ENZYME -> INHIBITOR
IC50
METABOLIC ENZYME -> INHIBITOR
Measured by testosterone 6β hydroxylation
REVERSIBLE
IC50
METABOLIC ENZYME -> INDUCER
mRNA levels in at least 2 hepatocyte cultures. Up 10 micromolar OTESECONAZOLE
METABOLIC ENZYME -> INDUCER
mRNA levels in at least 2 hepatocyte cultures. Up 10 micromolar OTESECONAZOLE
EXCRETED UNCHANGED
FECAL; URINE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC