ChEMBL logo

ChEMBL

spacer
ChEMBL Statistics
  Loading Statistics...
spacer

Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1138
CHEMBL1138
Compound Name EZETIMIBE
ChEMBL Synonyms EZETROL | SCH58235 | EZETIMIBE | ZETIA
Max Phase 4 (Approved)
Trade Names EZETROL | ZETIA | EZETIMIBE
Molecular Formula C24H21F2NO3

Additional synonyms for CHEMBL1138 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES O[C@@H](CC[C@@H]1[C@H](N(C1=O)c2ccc(F)cc2)c3ccc(O)cc3)c4ccc( ...
Download SMILES
Standard InChI InChI=1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23( ...
Download InChI
Standard InChI Key OLNTVTPDXPETLC-XPWALMASSA-N

Sources

  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1138

Molecule Features

CHEMBL1138 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Niemann-Pick C1-like protein 1 inhibitor Niemann-Pick C1-like protein 1 DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Coronary Artery DiseaseD003324EFO:0000378coronary artery disease3ClinicalTrials
Hepatitis C, ChronicD019698EFO:0004220Chronic Hepatitis C infection2ClinicalTrials
Lipid Metabolism DisordersD052439Orphanet:309005Disorder of lipid metabolism3ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection1ClinicalTrials
Hepatitis DD003699EFO:0007304hepatitis D2ClinicalTrials
HypertensionD006973EFO:0000537hypertension3ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma0ClinicalTrials
Aortic Valve StenosisD001024EFO:0000266aortic stenosis3ClinicalTrials
Non-alcoholic Fatty Liver DiseaseD065626EFO:0003095non-alcoholic fatty liver disease2ClinicalTrials
AtherosclerosisD050197EFO:0003914atherosclerosis0ClinicalTrials
Diabetes Mellitus, Type 2D003924EFO:0001360type II diabetes mellitus3ClinicalTrials
HypercholesterolemiaD006937HP:0003124hypercholesterolemia3ClinicalTrials
Acute Kidney InjuryD058186HP:0001919Acute kidney injury1ClinicalTrials
HyperlipidemiasD006949EFO:0003774hyperlipidemia3ClinicalTrials
Cardiovascular DiseasesD002318EFO:0000319cardiovascular disease4ATC
Metabolic SyndromeD024821EFO:0000195metabolic syndrome3ClinicalTrials

Clinical Data

ClinicalTrials.gov EZETIMIBE
The Cochrane Collaboration EZETIMIBE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1138. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL311 Glutamate [NMDA] receptor subunit epsilon 2 Rattus norvegicus 1.000
CHEMBL1881 Prostanoid EP2 receptor Homo sapiens 0.988
CHEMBL313 Serotonin transporter Rattus norvegicus 0.417

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL311 Glutamate [NMDA] receptor subunit epsilon 2 Rattus norvegicus 1.000
CHEMBL1881 Prostanoid EP2 receptor Homo sapiens 0.778
CHEMBL313 Serotonin transporter Rattus norvegicus 0.684

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
409.4 409.1489 4.89 6 60.77 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 2 0 4 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.72 - 3.96 3.96 3 30 0.57

Structural Alerts

There are 3 structural alerts for CHEMBL1138. To view alerts please click here.

Compound Cross References

ATC C - CARDIOVASCULAR SYSTEM
C10 - LIPID MODIFYING AGENTS
C10A - LIPID MODIFYING AGENTS, PLAIN
C10AX - Other lipid modifying agents
C10AX09 - ezetimibe

ChemSpider ChemSpider:OLNTVTPDXPETLC-XPWALMASSA-N
DailyMed ezetimibe
PubChem SID: 144204996 SID: 170465013 SID: 26719841
Wikipedia Ezetimibe

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1138



ACToR 163222-33-1
BindingDB 50371521
Brenda 151435
ChEBI 49040
ChemicalBook CB7380787
DrugBank DB00973
DrugCentral 1125
eMolecules 2736798
EPA CompTox Dashboard DTXSID1044223
FDA SRS EOR26LQQ24
Guide to Pharmacology 6816
Human Metabolome Database HMDB0015108
IBM Patent System 3AA5AF9BB11A457DCE4AC1BBC5199C00
LINCS LSM-5536
Mcule MCULE-4417284526
MolPort MolPort-005-938-627
NIH Clinical Collection SAM001246623
Nikkaji J900.924H
PharmGKB PA10816
PubChem 150311
PubChem: Drugs of the Future 12014979
PubChem: Thomson Pharma 14879623 14928749
Selleck Ezetimibe(Zetia)
SureChEMBL SCHEMBL2871
ZINC ZINC000003810860

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/OLNTVTPDXPETLC-XPWALMASSA-N spacer
spacer