ezetimibe   Click here for help

GtoPdb Ligand ID: 6816

Synonyms: SCH 58235 | SCH-58235 | Zetia®
Approved drug
ezetimibe is an approved drug (FDA (2002))
Compound class: Synthetic organic
Comment: Inhibits the intestinal cholesterol uptake protein Niemann-Pick C1-like protein 1 (NPC1L1). Analysis of cryo-EM structures reveals how NPC1L1 transports cholesterol and the mechanism of ezetimibe inhibition [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 60.77
Molecular weight 409.15
XLogP 4.46
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Oc1ccc(cc1)C1C(CCC(c2ccc(cc2)F)O)C(=O)N1c1ccc(cc1)F
Isomeric SMILES Oc1ccc(cc1)[C@@H]1[C@@H](CC[C@@H](c2ccc(cc2)F)O)C(=O)N1c1ccc(cc1)F
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
InChI Key OLNTVTPDXPETLC-XPWALMASSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2002))
IUPAC Name Click here for help
(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one
International Nonproprietary Names Click here for help
INN number INN
8010 ezetimibe
Synonyms Click here for help
SCH 58235 | SCH-58235 | Zetia®
Database Links Click here for help
CAS Registry No. 163222-33-1
ChEMBL Ligand CHEMBL1138
DrugBank Ligand DB00973
DrugCentral Ligand 1125
GtoPdb PubChem SID 178103422
PubChem CID 150311
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