Chemical Component Summary

Name(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
Identifiers(2R)-2-[2,4-bis(fluoranyl)phenyl]-1,1-bis(fluoranyl)-3-(1,2,3,4-tetrazol-1-yl)-1-[5-[4-[2,2,2-tris(fluoranyl)ethoxy]phenyl]pyridin-2-yl]propan-2-ol
FormulaC23 H16 F7 N5 O2
Molecular Weight527.394
TypeNON-POLYMER
Isomeric SMILESc1cc(ccc1c2ccc(nc2)C([C@](Cn3cnnn3)(c4ccc(cc4F)F)O)(F)F)OCC(F)(F)F
InChIInChI=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
InChIKeyIDUYJRXRDSPPRC-NRFANRHFSA-N

Chemical Details

Formal Charge0
Atom Count53
Chiral Atom Count1
Bond Count56
Aromatic Bond Count23

Drug Info: DrugBank

DrugBank IDDB13055 
NameOteseconazole
Groups
  • investigational
  • approved
DescriptionOteseconazole is an azole metalloenzyme inhibitor that targets fungal CYP51.[L41635] CYP51, also known as 14α demethylase, participates in the formation of ergosterol, a compound that plays a vital role in the integrity of cell membranes.[L41635,A247020] By binding and inhibiting CYP51, oteseconazole is active against most microorganisms associated with recurrent vulvovaginal candidiasis (RVVC).[L41635] Oteseconazole has demonstrated activity against _Candida albicans_, _Candida glabrata_, _Candida krusei_, _Candida parapsilosis_, _Candida tropicalis_, _Candida lusitaniae_ and _Candida dubliniensis_.[L41635] Unlike previous-generation azole antifungals, oteseconazole has a high selectivity for CYP51 and little interaction with human cytochrome P450s.[A247035] This is possible thanks to the tetrazole moiety in oteseconazole that increases target selectivity.[A247035] In contrast with oteseconazole, other antifungals with imidazole or triazole moieties, such as [ketoconazole] or [fluconazole], have a high number of drug-drug interactions due to their interaction with human CYPs.[A247050] The use of oteseconazole is contraindicated in females of reproductive potential due to its embryo-fetal toxicity risks.[L41635] This drug was approved by the FDA on April 26, 2022.[L41645]
Synonyms
  • 2-Pyridineethanol, α-(2,4difluorophenyl)-β β-difluoro- α-(1H-tetrazol-1-ylmethyl)-5-(4-(2,2,2-trifluoroethoxy)phenyl)-,(αR)
  • VT-1161
  • Oteseconazole
  • (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
Brand NamesVivjoa
IndicationOteseconazole is an azole antifungal indicated to reduce the incidence of recurrent vulvovaginal candidiasis (RVVC) in females with a history of RVVC who are not of reproductive potential.[L41635]
Categories
  • 14-alpha Demethylase Inhibitors
  • Antifungal Agents
  • Antiinfectives for Systemic Use
  • Antimycotics for Systemic Use
  • Azole Antifungals
ATC-CodeJ02AC06
CAS number1340593-59-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Cytochrome P450 51MAIVETVIDGINYFLSLSVTQQISILLGVPFVYNLVWQYLYSLRKDRAPL...unknowninhibitor
ATP-binding cassette sub-family G member 2MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...unknowninhibitor
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 77050711
ChEMBL CHEMBL3311228