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CHEBI:9448 - terbinafine

Default Structure
ChEBI IDCHEBI:9448
ChEBI Nameterbinafine
Stars
DefinitionA 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.
Last Modified22 February 2017
DownloadsMolfile
FormulaC21H25N
Net Charge0
Average Mass291.438
Monoisotopic Mass291.19870
SMILESCN(C/C=C/C#CC(C)(C)C)Cc1cccc2ccccc12
InChIInChI=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+
InChIKeyDOMXUEMWDBAQBQ-WEVVVXLNSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
P450 inhibitor  An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.
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).
anti-HBV agent  An antiviral agent that destroys or inhibits the replication of the hepatitis B virus.
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.
Applications:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
antifungal drug  Any antifungal agent used to prevent or treat fungal infections in humans or animals.
ChEBI Ontology
Outgoing Relation(s)
terbinafine (CHEBI:9448) has role anti-HBV agent (CHEBI:64951)
terbinafine (CHEBI:9448) has role anti-inflammatory agent (CHEBI:67079)
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 Relation(s)
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  Source
terbinafinaWHO MedNet
terbinafineKEGG DRUG
terbinafinumWHO MedNet
Synonyms  Source
(E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalene methanamineChemIDplus
(E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamineChemIDplus
SF 86-327ChEMBL
SF-86-327ChEMBL
TDT-067ChEMBL
terbinafineWHO MedNet
Brand Names  Source
LamasilChEMBL
Lamisil atChEMBL
Terbinafine component of osurniaChEMBL
Manual XrefsDatabases
2597DrugCentral
C08079KEGG COMPOUND
CPD-10571MetaCyc
D02375KEGG DRUG
DB00857DrugBank
HMDB0014995HMDB
TerbinafineWikipedia
Registry NumbersSources
Reaxys:4256376Reaxys
CAS:91161-71-6KEGG COMPOUND
CAS:91161-71-6ChemIDplus
Citations