efinaconazole (CHEBI:82718)

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ChEBI Name	efinaconazole

ChEBI ID	CHEBI:82718

Definition	A member of the class of triazoles that is butan-2-ol which is substituted at positions 1, 2, and 3 by 1,2,4-triazol-1-yl, 2,4-difluorophenyl, and 4-methylenepiperidin-1-yl groups, respectively (the 2R,3R stereoisomer). It is an antifungal drug used for the topical treatment of onychomycosis (a nail infection caused mainly by dermatophytes).

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Toni Morrison

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Formula

C18H22F2N4O

Net Charge

Average Mass

348.39030

Monoisotopic Mass

348.17617

InChI

InChI=1S/C18H22F2N4O/c1-13-5-7-23(8-6-13)14(2)18(25,10-24-12-21-11-22-24)16-4-3-15(19)9-17(16)20/h3-4,9,11-12,14,25H,1,5-8,10H2,2H3/t14-,18-/m1/s1

InChIKey

NFEZZTICAUWDHU-RDTXWAMCSA-N

SMILES

C[C@@H](N1CCC(=C)CC1)[C@](O)(Cn1cncn1)c1ccc(F)cc1F

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of EC 1.14.13.70 (sterol 14alpha-demethylase). antifungal drug Any antifungal agent used to prevent or treat fungal infections in humans or animals. (via conazole antifungal drug ) (via triazole antifungal drug ) ergosterol biosynthesis inhibitor Any compound that inhibits one or more steps in the pathway leading to the synthesis of ergosterol. (via conazole antifungal agent ) antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. (via conazole antifungal agent ) (via triazole antifungal agent )

Application(s):	antifungal drug Any antifungal agent used to prevent or treat fungal infections in humans or animals. (via conazole antifungal drug ) (via triazole antifungal drug )

ChEBI Ontology
Outgoing	efinaconazole (CHEBI:82718) has role EC 1.14.13.70 (sterol 14α-demethylase) inhibitor (CHEBI:77884) efinaconazole (CHEBI:82718) is a conazole antifungal drug (CHEBI:87071) efinaconazole (CHEBI:82718) is a olefinic compound (CHEBI:78840) efinaconazole (CHEBI:82718) is a organofluorine compound (CHEBI:37143) efinaconazole (CHEBI:82718) is a piperidines (CHEBI:26151) efinaconazole (CHEBI:82718) is a tertiary alcohol (CHEBI:26878) efinaconazole (CHEBI:82718) is a tertiary amino compound (CHEBI:50996) efinaconazole (CHEBI:82718) is a triazole antifungal drug (CHEBI:87101)

IUPAC Name

(2R,3R)-2-(2,4-difluorophenyl)-3-(4-methylenepiperidin-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Synonym	Source
KP-103	ChemIDplus

Brand Name	Source
JUBLIA	KEGG DRUG

Last Modified

22 February 2017