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CHEBI:599440 - amorolfine

Default Structure
ChEBI IDCHEBI:599440
ChEBI Nameamorolfine
Stars
DefinitionA member of the class of morpholines that is cis-2,6-dimethylmorpholine in which the hydrogen attached to the nitrogen is replaced by a racemic 2-methyl-3-[p-(2-methylbutan-2-yl)phenyl]propyl group. An inhibitor of the action of squalene monooxygenase, Δ14 reductase and D7-D8 isomerase and an antifungal agent, it is used (generally as its hydrochloride salt) for the topical treatment of fungal nail and skin infections.
Secondary ChEBI IDCHEBI:31779
Last Modified22 February 2017
DownloadsMolfile
FormulaC21H35NO
Net Charge0
Average Mass317.517
Monoisotopic Mass317.27186
SMILESCCC(C)(C)c1ccc(CC(C)CN2C[C@@H](C)O[C@@H](C)C2)cc1
InChIInChI=1S/C21H35NO/c1-7-21(5,6)20-10-8-19(9-11-20)12-16(2)13-22-14-17(3)23-18(4)15-22/h8-11,16-18H,7,12-15H2,1-6H3/t16?,17-,18+
InChIKeyMQHLMHIZUIDKOO-AYHJJNSGSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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).
EC 1.3.1.70 (Delta(14)-sterol reductase) inhibitor  An EC 1.3.1.* (oxidoreductase acting on donor CH-CH group, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of Δ14-sterol reductase (EC 1.3.1.70).
EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor  An EC 5.3.3.* (intramolecular oxidase transposing C=C bonds) inhibitor that interferes with the action of a cholestenol Δ-isomerase (EC 5.3.3.5).
antifungal drug  Any antifungal agent used to prevent or treat fungal infections in humans or animals.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Application:
antifungal drug  Any antifungal agent used to prevent or treat fungal infections in humans or animals.
ChEBI Ontology
Outgoing Relation(s)
amorolfine (CHEBI:599440) has role EC 1.14.13.132 (squalene monooxygenase) inhibitor (CHEBI:59285)
amorolfine (CHEBI:599440) has role EC 1.3.1.70 (Δ14-sterol reductase) inhibitor (CHEBI:83319)
amorolfine (CHEBI:599440) has role EC 5.3.3.5 (cholestenol Δ-isomerase) inhibitor (CHEBI:86385)
amorolfine (CHEBI:599440) is a morpholine antifungal drug (CHEBI:87135)
amorolfine (CHEBI:599440) is a tertiary amino compound (CHEBI:50996)
amorolfine (CHEBI:599440) is conjugate base of amorolfine(1+) (CHEBI:86380)
Incoming Relation(s)
amorolfine(1+) (CHEBI:86380) is conjugate acid of amorolfine (CHEBI:599440)
IUPAC Name 
(2R,6S)-2,6-dimethyl-4-{2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl}morpholine
INNs  Source
amorolfinaChemIDplus
amorolfineKEGG DRUG
amorolfinumChemIDplus
Synonyms  Source
(±)-cis-2,6-dimethyl-4-(2-methyl-3-(p-tert-pentylphenyl)propyl)morpholineChemIDplus
meso-2,6-dimethyl-4-{2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl}morpholineChEBI
meso-2,6-dimethyl-4-(2-methyl-3-(p-tert-pentylphenyl)propyl)morpholineChEBI
Manual XrefsDatabases
188DrugCentral
AmorolfineWikipedia
D01720KEGG DRUG
D02923KEGG DRUG
Registry NumbersSources
Beilstein:8154195Beilstein
CAS:78613-35-1ChemIDplus
CAS:78613-35-1KEGG DRUG
Citations