CHEBI:9448 - terbinafine

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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 0
Average Mass 291.42990
Monoisotopic Mass 291.199
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 )
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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
INNs Sources
terbinafina WHO MedNet
terbinafine KEGG DRUG
terbinafinum WHO MedNet
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
Manual Xrefs Databases
2597 DrugCentral
C08079 KEGG COMPOUND
CPD-10571 MetaCyc
D02375 KEGG DRUG
DB00857 DrugBank
HMDB0014995 HMDB
Terbinafine Wikipedia
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Registry Numbers Types Sources
4256376 Reaxys Registry Number Reaxys
91161-71-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017