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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL121
CHEMBL121
Compound Name ROSIGLITAZONE
ChEMBL Synonyms Avandamet | Avandaryl | BRL-49653 | Rosiglitazone | BRL-49653C | AVANDIA | ROSIGLITAZONE MALEATE | BRL-49653-C
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names AVANDIA | ROSIGLITAZONE MALEATE
Molecular Formula C18H19N3O3S

Additional synonyms for CHEMBL121 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN(CCOc1ccc(CC2SC(=O)NC2=O)cc1)c3ccccn3
Standard InChI InChI=1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5- ...
Download InChI
Standard InChI Key YASAKCUCGLMORW-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • BindingDB Database
  • British National Formulary
  • Curated Drug Pharmacokinetic Data
  • Deposited Supplementary Bioactivity Data
  • DrugMatrix
  • Open TG-GATEs
  • Orange Book
  • Patent Bioactivity Data
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL121

Molecule Features

CHEMBL121 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Withdrawal Information

Year 2010
Country European Union
Reason Increased risk of ischaemic heart disease
Class Cardiotoxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Peroxisome proliferator-activated receptor gamma agonist Peroxisome proliferator-activated receptor gamma DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
AnemiaD000740EFO:0004272anemia1ClinicalTrials
Glomerulosclerosis, Focal SegmentalD005923EFO:0004236focal segmental glomerulosclerosis1ClinicalTrials
AtherosclerosisD050197EFO:0003914atherosclerosis3ClinicalTrials
Alzheimer DiseaseD000544EFO:0000249Alzheimers disease3ClinicalTrials
Diabetes MellitusD003920EFO:0000400diabetes mellitus4ATC
ClinicalTrials
Diabetic NeuropathiesD003929EFO:1000783diabetic neuropathy3ClinicalTrials
Erectile DysfunctionD007172EFO:0004234erectile dysfunction1ClinicalTrials
NeoplasmsD009369EFO:0000311cancer1ClinicalTrials
EndometriosisD004715EFO:0001065endometriosis2ClinicalTrials
Lipid Metabolism DisordersD052439Orphanet:309005Disorder of lipid metabolism3ClinicalTrials
MalariaD008288EFO:0001068malaria1ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm1ClinicalTrials
Non-alcoholic Fatty Liver DiseaseD065626EFO:0003095non-alcoholic fatty liver disease2ClinicalTrials
Prediabetic StateD011236EFO:1001121prediabetes syndrome2ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer2ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0006859head and neck malignant neoplasia2ClinicalTrials
Leukoplakia, OralD007972HP:0002745Oral leukoplakia2ClinicalTrials
Glucose IntoleranceD018149HP:0000833Glucose intolerance3ClinicalTrials
Mycosis FungoidesD009182EFO:1001051mycosis fungoides2ClinicalTrials
NauseaD009325EFO:0006911Chemotherapy-induced nausea and vomiting1ClinicalTrials
Metabolic SyndromeD024821EFO:0000195metabolic syndrome3ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma1ClinicalTrials
Cognitive DysfunctionD060825HP:0100543cognitive impairment2ClinicalTrials
Diabetes Mellitus, Type 2D003924EFO:0001360type II diabetes mellitus4ClinicalTrials
ClinicalTrials
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
FDA
Malaria, FalciparumD016778EFO:0007444Plasmodium falciparum malaria1ClinicalTrials
Sezary SyndromeD012751EFO:1000785Sezary's disease2ClinicalTrials
Heart FailureD006333EFO:0000373congestive heart failure2ClinicalTrials
Insulin ResistanceD007333EFO:0002614insulin resistance3ClinicalTrials
SarcomaD012509EFO:0000691sarcoma2ClinicalTrials
Arthritis, RheumatoidD001172EFO:0000685rheumatoid arthritis2ClinicalTrials
AsthmaD001249EFO:0000270asthma2ClinicalTrials
Colitis, UlcerativeD003093EFO:0000729ulcerative colitis2ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection2ClinicalTrials
ClinicalTrials
Multiple Organ FailureD009102EFO:1001373Multiple Organ Failure3ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000673prostate adenocarcinoma3ClinicalTrials
Non-alcoholic Fatty Liver DiseaseD065626EFO:1001249non-alcoholic steatohepatitis2ClinicalTrials
Pituitary ACTH HypersecretionD047748EFO:1001110pituitary-dependent Cushing's disease2ClinicalTrials

Clinical Data

ClinicalTrials.gov ROSIGLITAZONE
The Cochrane Collaboration ROSIGLITAZONE

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 CHEMBL121. 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
CHEMBL2459 Peroxisome proliferator-activated receptor gamma Mus musculus 1.000
CHEMBL235 Peroxisome proliferator-activated receptor gamma Homo sapiens 1.000
CHEMBL1795168 CDGSH iron-sulfur domain-containing protein 1 Homo sapiens 1.000
CHEMBL239 Peroxisome proliferator-activated receptor alpha Homo sapiens 0.793
CHEMBL4422 Free fatty acid receptor 1 Homo sapiens 0.228

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2459 Peroxisome proliferator-activated receptor gamma Mus musculus 1.000
CHEMBL235 Peroxisome proliferator-activated receptor gamma Homo sapiens 1.000
CHEMBL1795168 CDGSH iron-sulfur domain-containing protein 1 Homo sapiens 1.000
CHEMBL4422 Free fatty acid receptor 1 Homo sapiens 0.994
CHEMBL239 Peroxisome proliferator-activated receptor alpha Homo sapiens 0.899

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
357.4 357.1147 2.49 7 71.53 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
6 1 0 6 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
6.34 6.5 3.02 1.93 2 25 0.82

Structural Alerts

There are 2 structural alerts for CHEMBL121. To view alerts please click here.

Compound Cross References

ATC A - ALIMENTARY TRACT AND METABOLISM
A10 - DRUGS USED IN DIABETES
A10B - BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
A10BG - Thiazolidinediones
A10BG02 - rosiglitazone

ChemSpider ChemSpider:YASAKCUCGLMORW-UHFFFAOYSA-N
DailyMed rosiglitazone maleate
PubChem SID: 144204987 SID: 170465417 SID: 174007204 SID: 26748954
Wikipedia Rosiglitazone

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL121



ACToR 122320-73-4
Atlas rosiglitazone
Brenda 83445 3404
ChEBI 50122
ChemicalBook CB7133275
DrugBank DB00412
DrugCentral 2405
eMolecules 902429
EPA CompTox Dashboard DTXSID7037131
Guide to Pharmacology 1056
Human Metabolome Database HMDB0005031
LINCS LSM-1949
Mcule MCULE-8293284864
MolPort MolPort-002-508-212
Nikkaji J620.770G
PharmGKB PA451283
PubChem 77999
PubChem: Drugs of the Future 50086904
PubChem: Thomson Pharma 14876617
Selleck Rosiglitazone-Avandia
SureChEMBL SCHEMBL5169

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