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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL408
CHEMBL408
Compound Name TROGLITAZONE
ChEMBL Synonyms CS-045 | PRELAY | GR-92132X | GR92132X | CI-991 | TROGLITAZONE | Rezulin
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names PRELAY | REZULIN
Molecular Formula C24H27NO5S

Additional synonyms for CHEMBL408 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Cc1c(C)c2OC(C)(COc3ccc(CC4SC(=O)NC4=O)cc3)CCc2c(C)c1O
Standard InChI InChI=1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4 ...
Download InChI
Standard InChI Key GXPHKUHSUJUWKP-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Drugs for Neglected Diseases Initiative (DNDi)
  • Orange Book
  • 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  • Withdrawn Drugs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


CHEMBL408

Molecule Features

CHEMBL408 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:N First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 1997
Country United States
Reason Hepatotoxicity

Mechanism of Action

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

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
DIABETES MELLITUSD003920EFO:0000400DIABETES MELLITUS4ATC

Clinical Data

ClinicalTrials.gov TROGLITAZONE
The Cochrane Collaboration TROGLITAZONE

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 CHEMBL408. 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 0.986
CHEMBL4422 Free fatty acid receptor 1 Homo sapiens 0.980
CHEMBL235 Peroxisome proliferator-activated receptor gamma Homo sapiens 0.641
CHEMBL242 Estrogen receptor beta Homo sapiens 0.304

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL3762 Voltage-gated L-type calcium channel alpha-1C subunit Rattus norvegicus 0.999
CHEMBL4422 Free fatty acid receptor 1 Homo sapiens 0.998
CHEMBL2459 Peroxisome proliferator-activated receptor gamma Mus musculus 0.997
CHEMBL235 Peroxisome proliferator-activated receptor gamma Homo sapiens 0.899
CHEMBL242 Estrogen receptor beta Homo sapiens 0.573

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
441.5 441.161 5.68 5 110.16 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
6 2 1 6 2 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
6.35 - 4.69 3.65 2 31 0.62

Structural Alerts

There are 2 structural alerts for CHEMBL408. 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
A10BG01 - troglitazone

ChemSpider ChemSpider:GXPHKUHSUJUWKP-UHFFFAOYSA-N
PubChem SID: 137275811 SID: 144205672 SID: 144210788 SID: 170465091 SID: 174007238 SID: 26755242 SID: 26755243 SID: 26757864 SID: 29216382
Wikipedia Troglitazone

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL408



ACToR 97322-87-7
Atlas troglitazone
Brenda 83446 3139
ChEBI 9753
DrugBank DB00197
DrugCentral 2767
eMolecules 594751
EPA CompTox Dashboard DTXSID8023719
Guide to Pharmacology 2693
LINCS LSM-4890
MolPort MolPort-003-666-725
Nikkaji J996.467C
PharmGKB PA451799
PubChem 5591
PubChem: Drugs of the Future 12013560
PubChem: Thomson Pharma 14905963
SureChEMBL SCHEMBL4959

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