EZETIMIBE

Search structure
Trade Names:
Synonyms:
Status: Approved (2002)
Entry Type: Small molecule
Molecule Category: Parent
ATC: C10AX09
UNII: EOR26LQQ24

Structure
InChI Key OLNTVTPDXPETLC-XPWALMASSA-N
Smile O=C1[C@H](CC[C@H](O)c2ccc(F)cc2)[C@@H](c2ccc(O)cc2)N1c1ccc(F)cc1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C24H21F2NO3
Molecular Weight 409.43
AlogP 4.89
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 6.0
Polar Surface Area 60.77
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 30.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Niemann-Pick C1-like protein 1 inhibitor DailyMed
Primary Target
NPC1 like intracellular cholesterol transporter 1
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - - 40
Other membrane protein
- - - 200 45-51
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 2-31
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 56000 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Cardiovascular Diseases 4 D002318 ClinicalTrials
Hyperlipoproteinemia Type II 4 D006938 ClinicalTrials
Aortic Valve Stenosis 3 D001024 ClinicalTrials
Hypertension 3 D006973 ClinicalTrials
Coronary Disease 3 D003327 ClinicalTrials
Metabolic Syndrome 3 D024821 ClinicalTrials
Lipid Metabolism Disorders 3 D052439 ClinicalTrials
Atherosclerosis 3 D050197 ClinicalTrials
Diabetes Mellitus, Type 2 3 D003924 ClinicalTrials
Hypertriglyceridemia 3 D015228 ClinicalTrials
Metabolism, Inborn Errors 3 D008661 ClinicalTrials
Diabetes Mellitus 3 D003920 ClinicalTrials
Myocardial Infarction 3 D009203 ClinicalTrials
Hepatitis D 2 D003699 ClinicalTrials
Non-alcoholic Fatty Liver Disease 2 D065626 ClinicalTrials
Hepatitis C, Chronic 2 D019698 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 0 D064129 ClinicalTrials

Related Entries

Scaffolds

Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Infections and infestations Upper respiratory tract infection 13.6
Infections and infestations Upper respiratory tract infection 13.0
Infections and infestations Upper respiratory tract infection 11.8
Infections and infestations Upper respiratory tract infection
Nervous system disorders Headache 8.0
Nervous system disorders Headache 7.3
Nervous system disorders Headache 6.3
Nervous system disorders Headache
Infections and infestations Sinusitis 4.6
Musculoskeletal and connective tissue disorders Arthralgia 4.3
Musculoskeletal and connective tissue disorders Back pain 4.3
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 4.3
Infections and infestations Upper respiratory tract infection 4.3
Musculoskeletal and connective tissue disorders Back pain 4.1
Gastrointestinal disorders Diarrhoea 4.1
Musculoskeletal and connective tissue disorders Back pain 3.9
Musculoskeletal and connective tissue disorders Arthralgia 3.8
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.8
Musculoskeletal and connective tissue disorders Back pain 3.7
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 3.7
Infections and infestations Nasopharyngitis 3.7
Infections and infestations Sinusitis 3.6
Gastrointestinal disorders Abdominal pain 3.5
Musculoskeletal and connective tissue disorders Back pain
Gastrointestinal disorders Gastrointestinal pain 3.5
Infections and infestations Sinusitis 3.5
Musculoskeletal and connective tissue disorders Arthralgia 3.4
Musculoskeletal and connective tissue disorders Back pain 3.4
Cardiac disorders Chest pain 3.4
Gastrointestinal disorders Diarrhoea 3.4
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.4
Infections and infestations Nasopharyngitis 3.3
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.2
Musculoskeletal and connective tissue disorders Myalgia 3.2
Gastrointestinal disorders Abdominal pain 3.1
Gastrointestinal disorders Gastrointestinal pain 3.1
Infections and infestations Infection 3.1
Infections and infestations Infestation 3.1
Gastrointestinal disorders Pharyngitis 3.1
Musculoskeletal and connective tissue disorders Arthralgia 3.0
Gastrointestinal disorders Diarrhoea 3.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.0
Gastrointestinal disorders Diarrhoea 2.9
Infections and infestations Upper respiratory tract infection 2.9
General disorders and administration site conditions Asthenia 2.8
Gastrointestinal disorders Diarrhoea 2.8
General disorders and administration site conditions Fatigue 2.8
Infections and infestations Sinusitis 2.8
Infections and infestations Upper respiratory tract infection 2.8
Gastrointestinal disorders Abdominal pain 2.7
Cardiac disorders Dizziness 2.7
Gastrointestinal disorders Gastrointestinal pain 2.7
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.7
Musculoskeletal and connective tissue disorders Myalgia 2.7
Musculoskeletal and connective tissue disorders Pain in extremity 2.7
Musculoskeletal and connective tissue disorders Arthralgia 2.6
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.6
Gastrointestinal disorders Diarrhoea 2.5
Gastrointestinal disorders Gastrointestinal disorder 2.5
Infections and infestations Infection 2.5
Infections and infestations Infestation 2.5
Musculoskeletal and connective tissue disorders Pain in extremity
Gastrointestinal disorders Pharyngitis 2.5
Infections and infestations Upper respiratory tract infection
Infections and infestations Upper respiratory tract infection 2.5
Musculoskeletal and connective tissue disorders Arthralgia 2.4
General disorders and administration site conditions Asthenia 2.4
Musculoskeletal and connective tissue disorders Back pain 2.4
General disorders and administration site conditions Fatigue 2.4
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.4
Gastrointestinal disorders Abdominal pain
Musculoskeletal and connective tissue disorders Arthralgia
Musculoskeletal and connective tissue disorders Back pain 2.3
Gastrointestinal disorders Gastrointestinal pain
Infections and infestations Infection 2.3
Infections and infestations Infestation 2.3
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Gastrointestinal disorders Pharyngitis 2.3
Musculoskeletal and connective tissue disorders Arthralgia
Gastrointestinal disorders Diarrhoea 2.2
Gastrointestinal disorders Gastrointestinal disorder 2.2
Infections and infestations Influenza 2.2
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Infections and infestations Sinusitis
Infections and infestations Sinusitis 2.2
Infections and infestations Viral infection 2.2
Infections and infestations Influenza 2.1
Musculoskeletal and connective tissue disorders Pain in extremity 2.1
Gastrointestinal disorders Pharyngitis 2.1
General disorders and administration site conditions Asthenia 2.0
Cardiac disorders Chest pain 2.0
General disorders and administration site conditions Fatigue 2.0
Infections and infestations Influenza 2.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.0
Musculoskeletal and connective tissue disorders Myalgia 2.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 1.9
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Fatigue 1.9
Infections and infestations Infection
Infections and infestations Infestation
Musculoskeletal and connective tissue disorders Pain in extremity 1.9
Gastrointestinal disorders Pharyngitis
Infections and infestations Sinusitis
Cardiac disorders Chest pain 1.8
Cardiac disorders Dizziness 1.8
Infections and infestations Viral infection 1.8
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.7
Musculoskeletal and connective tissue disorders Myalgia 1.7
General disorders and administration site conditions Asthenia 1.6
General disorders and administration site conditions Fatigue 1.6
General disorders and administration site conditions Asthenia
Gastrointestinal disorders Diarrhoea
General disorders and administration site conditions Fatigue
Infections and infestations Influenza
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.5
Musculoskeletal and connective tissue disorders Myalgia 1.5
General disorders and administration site conditions Asthenia 1.4
Cardiac disorders Dizziness 1.4
General disorders and administration site conditions Fatigue 1.4
Nervous system disorders Headache 1.4
Nervous system disorders Headache
Nervous system disorders Headache 1.3
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
Cardiac disorders Chest pain
Cardiac disorders Dizziness
Gastrointestinal disorders Flatulence 1.1
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Flatulence 1.0
Investigations Alanine aminotransferase increased 0.6
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 0.5
Musculoskeletal and connective tissue disorders Myalgia 0.5
Musculoskeletal and connective tissue disorders Arthralgia 0.3
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 0.3
Cardiac disorders Dizziness 0.2
Investigations Gamma-glutamyltransferase increased 0.2

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Musculoskeletal and connective tissue disorders
14.43
General disorders and administration site conditions
12.95
Nervous system disorders
9.91
Gastrointestinal disorders
9.29
Investigations
6.34
Vascular disorders
6.1
Cardiac disorders
5.96
Skin and subcutaneous tissue disorders
5.21
Respiratory, thoracic and mediastinal disorders
4.27
Injury, poisoning and procedural complications
4.07
Psychiatric disorders
3.81
Immune system disorders
3.08
Renal and urinary disorders
2.1

Cross References

Resources Reference
CAS NUMBER 163222-33-1
ChEBI 49040
ChEMBL CHEMBL1138
DrugBank DB00973
DrugCentral 1125
EPA CompTox DTXSID1044223
FDA SRS EOR26LQQ24
Human Metabolome Database HMDB0015108
Guide to Pharmacology 6816
KEGG D00434
PDB H56
PharmGKB PA10816
PubChem 150311
SureChEMBL SCHEMBL2871
ZINC ZINC000003810860
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