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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1496
CHEMBL1496
Compound Name ROSUVASTATIN
ChEMBL Synonyms ROSUVASTATIN | S-4522 | ROSUVASTATIN CALCIUM | ZD-4522 | CRESTOR | ZD4522 (CALCIUM SALT)
Max Phase 4 (Approved)
Trade Names ROSUVASTATIN CALCIUM | CRESTOR
Molecular Formula C22H28FN3O6S

Additional synonyms for CHEMBL1496 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC(C)c1nc(nc(c2ccc(F)cc2)c1\C=C\[C@@H](O)C[C@@H](O)CC(=O)O)N ...
Download SMILES
Standard InChI InChI=1S/C22H28FN3O6S/c1-13(2)20-18(10-9-16(27)11-17(28)12-1 ...
Download InChI
Standard InChI Key BPRHUIZQVSMCRT-VEUZHWNKSA-N

Sources

  • BindingDB Database
  • British National Formulary
  • Gene Expression Atlas Compounds
  • Orange Book
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1496

Molecule Features

CHEMBL1496 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
HMG-CoA reductase inhibitor HMG-CoA reductase DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Crohn DiseaseD003424EFO:0000384Crohn's disease1ClinicalTrials
Diabetes Mellitus, Type 2D003924EFO:0001360type II diabetes mellitus3ClinicalTrials
ClinicalTrials
HIV InfectionsD015658EFO:0000180HIV-1 infection3ClinicalTrials
HypertensionD006973EFO:0000537hypertension3ClinicalTrials
HypertriglyceridemiaD015228EFO:0004211Hypertriglyceridemia1ClinicalTrials
MalariaD008288EFO:0001068malaria1ClinicalTrials
Orthomyxoviridae InfectionsD009976EFO:0005226swine influenza2ClinicalTrials
SepsisD018805HP:0100806sepsis2ClinicalTrials
Aortic Valve StenosisD001024EFO:0000266aortic stenosis3ClinicalTrials
Diabetic NeuropathiesD003929EFO:1000783diabetic neuropathy2ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection3ClinicalTrials
Heart FailureD006333EFO:0003144heart failure3ClinicalTrials
ClinicalTrials
Hyperlipoproteinemia Type IIID006952Orphanet:412Hyperlipoproteinemia type 33ClinicalTrials
NeoplasmsD009369EFO:0000311cancer1ClinicalTrials
PeriodontitisD010518EFO:0000649periodontitis2ClinicalTrials
Scleroderma, SystemicD012595EFO:0000717systemic scleroderma3ClinicalTrials
Diabetes Mellitus, Type 1D003922EFO:0001359type I diabetes mellitus3ClinicalTrials
Hyperlipidemia, Familial CombinedD006950Orphanet:79211Combined hyperlipidemia3ClinicalTrials
Acute Coronary SyndromeD054058EFO:0005672acute coronary syndrome3ClinicalTrials
ClinicalTrials
Cardiomyopathy, DilatedD002311EFO:0000407dilated cardiomyopathy3ClinicalTrials
Cell DeathD016923GO:0008219cell death3ClinicalTrials
HypercholesterolemiaD006937HP:0003124hypercholesterolemia3ClinicalTrials
ClinicalTrials
Immune System DiseasesD007154EFO:0000540immune system disease1ClinicalTrials
Metabolic SyndromeD024821EFO:0000195metabolic syndrome3ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm1ClinicalTrials
Pre-EclampsiaD011225EFO:0000668preeclampsia1ClinicalTrials
Renal InsufficiencyD0514371ClinicalTrials
AsthmaD001249EFO:0000270asthma1ClinicalTrials
AtherosclerosisD050197EFO:0003914atherosclerosis3ClinicalTrials
Lipid Metabolism DisordersD052439Orphanet:309005Disorder of lipid metabolism3ClinicalTrials
ClinicalTrials
Metabolic DiseasesD008659EFO:0000589metabolic disease1ClinicalTrials
ObesityD009765EFO:0001073obesity3ClinicalTrials
Rectal NeoplasmsD012004EFO:1000657rectum cancer2ClinicalTrials
Arthritis, RheumatoidD001172EFO:0000685rheumatoid arthritis2ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression2ClinicalTrials
Friedreich AtaxiaD005621Orphanet:95Friedreich ataxia0ClinicalTrials
Myocardial InfarctionD009203EFO:0000612myocardial infarction2ClinicalTrials
Non-alcoholic Fatty Liver DiseaseD065626EFO:1001249non-alcoholic steatohepatitis1ClinicalTrials
Skin DiseasesD012871EFO:0000701skin disease1ClinicalTrials
Acquired Immunodeficiency SyndromeD000163EFO:0000765AIDS1ClinicalTrials
AmnesiaD000647EFO:1001454amnesia2ClinicalTrials
AnemiaD000740EFO:0004272anemia1ClinicalTrials
Angioedemas, HereditaryD054179Orphanet:91378Hereditary angioedema1ClinicalTrials
Anti-Neutrophil Cytoplasmic Antibody-Associated VasculitisD056648EFO:0004826anti-neutrophil antibody associated vasculitis3ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma3ClinicalTrials
HyperlipidemiasD006949EFO:0003774hyperlipidemia3ClinicalTrials
Lupus Erythematosus, SystemicD008180EFO:0002690systemic lupus erythematosus1ClinicalTrials
StrokeD020521EFO:0000712stroke3ClinicalTrials
Cerebral HemorrhageD002543EFO:0005669intracerebral hemorrhage2ClinicalTrials
Coronary Artery DiseaseD003324EFO:0000378coronary artery disease3ClinicalTrials
ClinicalTrials
Heart FailureD006333EFO:0000373congestive heart failure3ClinicalTrials
Hepatitis CD006526EFO:0003047hepatitis C infection2ClinicalTrials
Hip FracturesD006620EFO:0003964hip fracture3ClinicalTrials
Hyperlipoproteinemia Type IID006938Orphanet:391665Homozygous familial hypercholesterolemia3ClinicalTrials
IschemiaD007511EFO:0000556ischemia2ClinicalTrials
Venous ThromboembolismD054556EFO:0004286venous thromboembolism2ClinicalTrials
Wounds and InjuriesD014947EFO:0000546injury1ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma2ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma1ClinicalTrials
Cardiovascular DiseasesD002318EFO:0000319cardiovascular disease4ATC
Coronary DiseaseD003327EFO:0001645coronary heart disease3ClinicalTrials
Diabetes MellitusD003920EFO:0000400diabetes mellitus2ClinicalTrials
ClinicalTrials
Hyperlipoproteinemia Type IID006938EFO:0004911familial hypercholesterolemia3ClinicalTrials
ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000673prostate adenocarcinoma1ClinicalTrials
Pulmonary Disease, Chronic ObstructiveD029424EFO:0000341chronic obstructive pulmonary disease2ClinicalTrials

Clinical Data

ClinicalTrials.gov ROSUVASTATIN
The Cochrane Collaboration ROSUVASTATIN

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 CHEMBL1496. 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
CHEMBL3247 HMG-CoA reductase Rattus norvegicus 1.000
CHEMBL402 HMG-CoA reductase Homo sapiens 1.000

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL3247 HMG-CoA reductase Rattus norvegicus 1.000
CHEMBL402 HMG-CoA reductase Homo sapiens 1.000

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
481.6 481.1683 2.4 10 140.92 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
7 3 0 9 3 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.25 - .89 -2.24 2 33 0.47

Structural Alerts

There are 2 structural alerts for CHEMBL1496. To view alerts please click here.

Compound Cross References

ATC C - CARDIOVASCULAR SYSTEM
C10 - LIPID MODIFYING AGENTS
C10A - LIPID MODIFYING AGENTS, PLAIN
C10AA - HMG CoA reductase inhibitors
C10AA07 - rosuvastatin

ChemSpider ChemSpider:BPRHUIZQVSMCRT-VEUZHWNKSA-N
DailyMed rosuvastatin calcium
Wikipedia Rosuvastatin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1496



Atlas Rosuvastatin
BindingDB 18372
Brenda 8562
ChEBI 38545
DrugBank DB01098
DrugCentral 2406
eMolecules 877496
EPA CompTox Dashboard DTXSID8048492
FDA SRS 413KH5ZJ73
Guide to Pharmacology 2954
Human Metabolome Database HMDB0015230
IBM Patent System B0E78E11E390F832E3994E0C365BE7E3
LINCS LSM-43032
MolPort MolPort-000-883-884
Nikkaji J3.118.169K
PubChem 446157
PubChem: Thomson Pharma 14834808 14810118
SureChEMBL SCHEMBL2520
ZINC ZINC000001535101

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