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Compound Detail

CHEMBL1138

EZETIMIBE
💊 Approved Drug
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💊 Approved Drug
O=C1[C@H](CC[C@H](O)c2ccc(F)cc2)[C@@H](c2ccc(O)cc2)N1c1ccc(F)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1138
Name EZETIMIBE
Phase Approved
Structure Type MOL
InChI Key OLNTVTPDXPETLC-XPWALMASSA-N
Therapeutic ✓ Yes

Known Names

Ezetimiba Ezetimibe Ezetimibe component of k-924 Ezetimibe component of liptruzet Ezetimibe component of nexlizet Ezetimibe component of roszet Ezetimibe component of vytorin Ezetrol MK0653 NSC-758923 SCH-58235 SCH58235 +1 more
9
Targets
9
Activities
3
Assay Types
21
PK Parameters
20
Publications
13
Known Names
20
Indications
1
Mechanisms

Molecular Properties

409.4
MW (Da)
4.89
ALogP
3
HBA
2
HBD
60.8
PSA (Ų)
0.57
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2002
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral
USAN Stem -imibe
USAN Year 1999

Extended Properties

Molecular Formula C24H21F2NO3
MW 409.43
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness 0.03

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Niemann-Pick C1-like protein 1 inhibitor INHIBITOR NPC1-like intracellular cholesterol transporter 1 ✓ ✓

Indications

Cardiovascular Diseases Hypercholesterolemia Hyperlipidemias Hyperlipoproteinemia Type II Hyperlipoproteinemia Type II Aortic Valve Stenosis Atherosclerosis Coronary Disease Diabetes Mellitus Diabetes Mellitus, Type 2 Hypertension Hypertriglyceridemia Lipid Metabolism Disorders Metabolic Syndrome Metabolism, Inborn Errors Myocardial Infarction Hepatitis C, Chronic Hepatitis D Non-alcoholic Fatty Liver Disease HIV Infections

ATC Classification

C10AX09
ezetimibe
Level 1: CARDIOVASCULAR SYSTEM
Level 2: LIPID MODIFYING AGENTS

Activity Summary

IC50 6 meas. best 6.43
Ki 2 meas. best 6.7
EC50 1 meas. best 4.98

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NPC1-like intracellular cholesterol transporter 1
CHEMBL5161
 Ki 6.7 6.7 200.0 1
NPC1-like intracellular cholesterol transporter 1
CHEMBL2027
 IC50 6.43 6.43 370.0 1
Hepatitis delta virus
CHEMBL4888466
 EC50 4.98 4.98 10400.0 1
dengue virus type 3
CHEMBL612717
 IC50 4.88 4.88 13070.0 1
dengue virus type 1
CHEMBL613360
 IC50 4.88 4.88 13070.0 1
dengue virus type 4
CHEMBL613728
 IC50 4.88 4.88 13070.0 1
dengue virus type 2
CHEMBL613966
 IC50 4.88 4.88 13070.0 1
Hepatic sodium/bile acid cotransporter
CHEMBL5287
 Ki 4.6 4.6 25000.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.25 4.25 56000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1311.81 ng.hr.mL-1 Homo sapiens
CL 23.8 mL.min-1.g-1 Homo sapiens
CL 23.8 mL.min-1.g-1 Homo sapiens
CL 6.34 mL.min-1.g-1 Homo sapiens
CL 207.0 mL.min-1.g-1 Homo sapiens
CL 8.61 mL.min-1.g-1 Homo sapiens
CL 3.78 mL.min-1.g-1 Homo sapiens
CL 117.0 mL.min-1.g-1 Homo sapiens
CL 1160.0 mL.min-1.g-1 Homo sapiens
CL 418.0 mL.min-1.g-1 Homo sapiens
CL 495.0 mL.min-1.g-1 Homo sapiens
CL 295.0 mL.min-1.g-1 Homo sapiens
CL 5180.0 mL.min-1.g-1 Homo sapiens
CL 2930.0 mL.min-1.g-1 Homo sapiens
Fu 0.05 - Homo sapiens
Fu 0.18 - Homo sapiens
Fu 0.18 - Homo sapiens
Fu 0.3 - Homo sapiens
T1/2 0.7167 hr Rattus norvegicus
T1/2 0.1583 hr Rattus norvegicus
T1/2 22.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NPC1-like intracellular cholesterol transporter 1 Ki = 200.0 nM 6.7 Displacement of [3H]ezetimibe-glucuronide from NPC1L1 in Sprague-Dawley rat brus... 18063367
NPC1-like intracellular cholesterol transporter 1 IC50 = 370.0 nM 6.43 Inhibition of NPC1L1 (unknown origin) assessed as inhibition of cholesterol cell... 35063734
Hepatitis delta virus EC50 = 10400.0 nM 4.98 Antiviral activity against hepatitis D virus infected in human Huh-7 cells overe... 36111355
dengue virus type 1 IC50 = 13070.0 nM 4.88 Antiviral activity against DENV1 infected in human Huh7 cells assessed as reduct... 31128447
dengue virus type 2 IC50 = 13070.0 nM 4.88 Antiviral activity against DENV2 New Guinea infected in human Huh7 cells assesse... 31128447
dengue virus type 3 IC50 = 13070.0 nM 4.88 Antiviral activity against DENV3 infected in human Huh7 cells assessed as reduct... 31128447
dengue virus type 4 IC50 = 13070.0 nM 4.88 Antiviral activity against DENV2 H241 infected in human Huh7 cells assessed as r... 31128447
Hepatic sodium/bile acid cotransporter Ki = 25000.0 nM 4.6 Binding affinity to NTCP (unknown origin) 36111355
Bile salt export pump IC50 = 56000.0 nM 4.25 Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... 23956101

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 88
31188588 10.1021/acs.jmedchem.9b00428 Unchecked 24
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
22275465 10.1124/dmd.111.043984 UDP-glucuronosyltransferase 1A1 12
31188588 10.1021/acs.jmedchem.9b00428 N-acetylgalactosamine-6-sulfatase 11
9526571 10.1021/jm970701f ADMET 10
22112382 10.1124/dmd.111.041095 Plasma 8
22112382 10.1124/dmd.111.041095 ADMET 8
- 10.1007/s00044-012-0263-z Rattus norvegicus 7
22275465 10.1124/dmd.111.043984 ADMET 6
26783178 10.1016/j.bmcl.2015.12.077 Hamster 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
22275465 10.1124/dmd.111.043984 Liver microsome 5
25305716 10.1016/j.ejmech.2014.10.014 Mus musculus 5
29496412 10.1016/j.bmc.2017.08.046 NPC1-like intracellular cholesterol transporter 1 5
25882530 10.1016/j.bmc.2015.03.067 ADMET 4
25882530 10.1016/j.bmc.2015.03.067 Mus musculus 4
33725656 10.1016/j.ejmech.2021.113358 Unchecked 4
14695813 10.1021/jm030283g Homo sapiens 4
25305716 10.1016/j.ejmech.2014.10.014 ADMET 4

Data from ChEMBL 36 via Core Engine