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CHEBI:49040 - ezetimibe

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ChEBI Name ezetimibe
ChEBI ID CHEBI:49040
Definition A β-lactam that is azetidin-2-one which is substituted at 1, 3, and 4 by p-fluorophenyl, 3-(p-fluorophenyl)-3-hydroxypropyl, and 4-hydroxyphenyl groups, respectively (the 3R,3'S,4S enantiomer).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C24H21F2NO3
Net Charge 0
Average Mass 409.42520
Monoisotopic Mass 409.149
InChI InChI=1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21-,22+,23-/m1/s1
InChIKey OLNTVTPDXPETLC-XPWALMASSA-N
SMILES [H][C@]1(CC[C@H](O)c2ccc(F)cc2)C(=O)N(c2ccc(F)cc2)[C@]1([H])c1ccc(O)cc1
Roles Classification
Biological Role(s): antimetabolite
A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
Application(s): anticholesteremic drug
A substance used to lower plasma cholesterol levels.
antilipemic drug
A substance used to treat hyperlipidemia (an excess of lipids in the blood).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ezetimibe (CHEBI:49040) has role anticholesteremic drug (CHEBI:35821)
ezetimibe (CHEBI:49040) has role antilipemic drug (CHEBI:35679)
ezetimibe (CHEBI:49040) has role antimetabolite (CHEBI:35221)
ezetimibe (CHEBI:49040) is a β-lactam (CHEBI:35627)
ezetimibe (CHEBI:49040) is a azetidines (CHEBI:38777)
ezetimibe (CHEBI:49040) is a organofluorine compound (CHEBI:37143)
IUPAC Name
(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one
INNs Sources
ezetimiba WHO MedNet
ézétimibe WHO MedNet
ezetimibe ChemIDplus
ezetimibum WHO MedNet
Brand Names Sources
Ezedoc DrugBank
Ezetrol DrugBank
Zetia KEGG DRUG
Database Links Databases
D01966 KEGG DRUG
DB00973 DrugBank
Ezetimibe Wikipedia
HMDB15108 HMDB
LSM-5536 LINCS
View more database links
Registry Numbers Types Sources
163222-33-1 CAS Registry Number ChemIDplus
7981967 Reaxys Registry Number Reaxys
7981967 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
17587760 PubMed citation Europe PMC
18585981 PubMed citation Europe PMC
23219178 PubMed citation Europe PMC
23266293 PubMed citation Europe PMC
23317398 PubMed citation Europe PMC
23471229 PubMed citation Europe PMC
23510093 PubMed citation Europe PMC
23538020 PubMed citation Europe PMC
Last Modified
25 February 2016