CHEBI:7451 - naftifine

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ChEBI Name naftifine
ChEBI ID CHEBI:7451
Definition A tertiary amine in which the nitrogen is substituted by methyl, α-naphthylmethyl, and (1E)-cinnamyl groups. It is used (usually as its hydrochloride salt) for the treatment of fungal skin infections.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H21N
Net Charge 0
Average Mass 287.39810
Monoisotopic Mass 287.167
InChI InChI=1S/C21H21N/c1-22(16-8-11-18-9-3-2-4-10-18)17-20-14-7-13-19-12-5-6-15-21(19)20/h2-15H,16-17H2,1H3/b11-8+
InChIKey OZGNYLLQHRPOBR-DHZHZOJOSA-N
SMILES CN(C\C=C\c1ccccc1)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).
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 )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing naftifine (CHEBI:7451) has role EC 1.14.13.132 (squalene monooxygenase) inhibitor (CHEBI:59285)
naftifine (CHEBI:7451) has role sterol biosynthesis inhibitor (CHEBI:83317)
naftifine (CHEBI:7451) is a allylamine antifungal drug (CHEBI:87127)
naftifine (CHEBI:7451) is a naphthalenes (CHEBI:25477)
naftifine (CHEBI:7451) is a tertiary amine (CHEBI:32876)
IUPAC Name
(2E)-N-methyl-N-(1-naphthylmethyl)-3-phenylprop-2-en-1-amine
INNs Sources
naftifina WHO MedNet
naftifine WHO MedNet
naftifine KEGG DRUG
naftifinum WHO MedNet
Synonyms Sources
(E)-N-cinnamyl-N-methyl-1-naphthalenemethylamine ChemIDplus
naftifin ChemIDplus
trans-N-cinnamyl-N-methyl-(1-naphthylmethyl)amine ChEBI
Manual Xrefs Databases
1872 DrugCentral
BE853976 Patent
C08071 KEGG COMPOUND
D08245 KEGG DRUG
DB00735 DrugBank
HMDB0014873 HMDB
Naftifine Wikipedia
US4282251 Patent
View more database links
Registry Numbers Types Sources
2983617 Reaxys Registry Number Reaxys
65472-88-0 CAS Registry Number KEGG COMPOUND
65472-88-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
18212112 PubMed citation Europe PMC
24196340 PubMed citation Europe PMC
25294700 PubMed citation Europe PMC
6388170 PubMed citation Europe PMC
Last Modified
22 February 2017