terbinafine (CHEBI:9448)

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ChEBI Name	terbinafine

ChEBI ID	CHEBI:9448

Definition	A tertiary amine that is N-methyl-1-naphthalenemethylamine in which the amino hydrogen is replaced by a 3-(tertbutylethynyl)allyl group. An antifungal agent administered orally (generally as the hydrochloride salt) for the treatment of skin and nail infections.

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

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Formula

C21H25N

Net Charge

Average Mass

291.42990

Monoisotopic Mass

291.19870

InChI

InChI=1S/C21H25N/c1-21(2,3)15-8-5-9-16-22(4)17-19-13-10-12-18-11-6-7-14-20(18)19/h5-7,9-14H,16-17H2,1-4H3/b9-5+

InChIKey

DOMXUEMWDBAQBQ-WEVVVXLNSA-N

SMILES

CN(C\C=C\C#CC(C)(C)C)Cc1cccc2ccccc12

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 1.14.13.132 (squalene monooxygenase) 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 squalene monooxygenase (EC 1.14.13.132). P450 inhibitor An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances. sterol biosynthesis inhibitor Any compound that inhibits the biosynthesis of any sterol. antifungal drug Any antifungal agent used to prevent or treat fungal infections in humans or animals. (via allylamine antifungal drug )

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

ChEBI Ontology
Outgoing	terbinafine (CHEBI:9448) has role EC 1.14.13.132 (squalene monooxygenase) inhibitor (CHEBI:59285) terbinafine (CHEBI:9448) has role P450 inhibitor (CHEBI:50183) terbinafine (CHEBI:9448) has role sterol biosynthesis inhibitor (CHEBI:83317) terbinafine (CHEBI:9448) is a acetylenic compound (CHEBI:73474) terbinafine (CHEBI:9448) is a allylamine antifungal drug (CHEBI:87127) terbinafine (CHEBI:9448) is a enyne (CHEBI:59831) terbinafine (CHEBI:9448) is a naphthalenes (CHEBI:25477) terbinafine (CHEBI:9448) is a tertiary amine (CHEBI:32876) terbinafine (CHEBI:9448) is conjugate base of terbinafine(1+) (CHEBI:77615)

Incoming	terbinafine(1+) (CHEBI:77615) is conjugate acid of terbinafine (CHEBI:9448)

IUPAC Name

(2E)-N,6,6-trimethyl-N-(1-naphthylmethyl)hept-2-en-4-yn-1-amine

Synonyms	Sources
(E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalene methanamine	ChemIDplus
(E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamine	ChemIDplus
terbinafine	WHO MedNet

Last Modified

22 February 2017