ezetimibe   Click here for help

GtoPdb Ligand ID: 6816

Synonyms: SCH 58235 | SCH-58235 | Zetia®
Approved drug PDB Ligand
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
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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
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Summary of Clinical Use Click here for help
Used to lower cholesterol levels
Mechanism Of Action and Pharmacodynamic Effects Click here for help
An anti-hyperlipidemic medication; binds to the Niemann-Pick C1-Like 1 protein (NPC1L1, a critical mediator of cholesterol absorption) on gastrointestinal tract epithelial cells and in hepatocytes.
Pharmacokinetics Click here for help
Population pharmacokinetics
It has been reported that polymorphisms of the hepatic organic anion transporting polypeptides (OATPs) influence the pharmacokinetics of ezetimibe (in healthy subjects given a single dose) [3]