VT1

(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

Created:	2015-02-26
Last modified:	2015-12-02

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4 entries where VT1 is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	53
Chiral Atom Count	1
Bond Count	56
Aromatic Bond Count	23

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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
Systematic Name (OpenEye OEToolkits)	(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
Formula	C₂₃ H₁₆ F₇ N₅ O₂
Molecular Weight	527.394
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	FC(F)(F)COc1ccc(cc1)c2ccc(nc2)C(F)(F)C(O)(c3ccc(F)cc3F)Cn4nnnc4
SMILES	CACTVS	3.385	O[C](Cn1cnnn1)(c2ccc(F)cc2F)C(F)(F)c3ccc(cn3)c4ccc(OCC(F)(F)F)cc4
SMILES	OpenEye OEToolkits	1.7.6	c1cc(ccc1c2ccc(nc2)C(C(Cn3cnnn3)(c4ccc(cc4F)F)O)(F)F)OCC(F)(F)F
Canonical SMILES	CACTVS	3.385	O[C@@](Cn1cnnn1)(c2ccc(F)cc2F)C(F)(F)c3ccc(cn3)c4ccc(OCC(F)(F)F)cc4
Canonical SMILES	OpenEye OEToolkits	1.7.6	c1cc(ccc1c2ccc(nc2)C([C@](Cn3cnnn3)(c4ccc(cc4F)F)O)(F)F)OCC(F)(F)F
InChI	InChI	1.03	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
InChIKey	InChI	1.03	IDUYJRXRDSPPRC-NRFANRHFSA-N

Drug Info: DrugBank

DrugBank ID	DB13055
Name	Oteseconazole
Groups	approved investigational
Description	Oteseconazole 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	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 2-Pyridineethanol, α-(2,4difluorophenyl)-β β-difluoro- α-(1H-tetrazol-1-ylmethyl)-5-(4-(2,2,2-trifluoroethoxy)phenyl)-,(αR) VT-1161
Brand Names	Vivjoa
Indication	Oteseconazole 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 BCRP/ABCG2 Inhibitors Tetrazoles Triazole and tetrazole derivatives
ATC-Code	J02AC06
CAS number	1340593-59-0

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Cytochrome P450 51	MAIVETVIDGINYFLSLSVTQQISILLGVPFVYNLVWQYLYSLRKDRAPL...	unknown	inhibitor
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	inhibitor

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