troglitazone Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
peroxisome proliferator activating receptor-gamma (PPAR-gamma) agonists, thiazolidinedione derivatives 2767 97322-87-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • CS-045
  • rezulin
  • troglitazone
  • romglizone
A chroman and thiazolidinedione derivative that acts as a PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS (PPAR) agonist. It was formerly used in the treatment of TYPE 2 DIABETES MELLITUS, but has been withdrawn due to hepatotoxicity.
  • Molecular weight: 441.54
  • Formula: C24H27NO5S
  • CLOGP: 5.59
  • LIPINSKI: 1
  • HAC: 6
  • HDO: 2
  • TPSA: 84.86
  • ALOGS: -5.56
  • ROTB: 5

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.40 g O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 22.65 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Hosey CM, Chan R, Benet LZ
BA (Bioavailability) 45 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Jan. 29, 1997 FDA PFIZER PHARMS

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC A10BG01 ALIMENTARY TRACT AND METABOLISM
DRUGS USED IN DIABETES
BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
Thiazolidinediones
CHEBI has role CHEBI:22586 antioxidants
CHEBI has role CHEBI:35526 hypoglycemic drug
CHEBI has role CHEBI:35610 cytostatic
CHEBI has role CHEBI:35620 vasodilator
CHEBI has role CHEBI:35623 antiepileptic
CHEBI has role CHEBI:50249 anticoagulante
CHEBI has role CHEBI:50427 platelet aggregation inhibitors
MeSH PA D007004 Hypoglycemic Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Diabetes mellitus type 2 indication 44054006 DOID:9352

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 6.33 acidic
pKa2 12.07 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Peroxisome proliferator-activated receptor gamma Nuclear hormone receptor AGONIST EC50 6.27 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 2B GPCR Ki 6.08 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 5.53 DRUG MATRIX
Carbonic anhydrase 2 Enzyme IC50 6.01 DRUG MATRIX
Cytochrome P450 2C9 Enzyme IC50 5.40 DRUG MATRIX
Thromboxane-A synthase Enzyme IC50 5.53 DRUG MATRIX
Mitogen-activated protein kinase 1 Kinase IC50 5.91 DRUG MATRIX
Glycogen [starch] synthase, liver Enzyme WOMBAT-PK
Aldose reductase Enzyme WOMBAT-PK
Cytochrome P450 3A4 Enzyme Km 3.21 WOMBAT-PK
Tyrosine-protein phosphatase non-receptor type 1 Enzyme IC50 4.26 CHEMBL
Amine oxidase [flavin-containing] A Enzyme Ki 4.98 CHEMBL
Amine oxidase [flavin-containing] B Enzyme Ki 5.02 CHEMBL
UDP-glucuronosyltransferase 1-6 Enzyme Ki 4.70 CHEMBL
Bile salt export pump Transporter IC50 5.57 CHEMBL
Aldose reductase Enzyme IC50 5.69 DRUG MATRIX
Indoleamine 2,3-dioxygenase 2 Enzyme IC50 5.35 CHEMBL
Amine oxidase [flavin-containing] B Enzyme Ki 4.96 CHEMBL
Indoleamine 2,3-dioxygenase 1 Enzyme IC50 4.21 CHEMBL
Amine oxidase [flavin-containing] A Enzyme Ki 5.32 CHEMBL
Bile salt export pump Unclassified IC50 4.97 CHEMBL

External reference:

IDSource
4020997 VUID
N0000148466 NUI
D00395 KEGG_DRUG
4020997 VANDF
C0056565 UMLSCUI
CHEBI:9753 CHEBI
TDZ PDB_CHEM_ID
CHEMBL408 ChEMBL_ID
D000077288 MESH_DESCRIPTOR_UI
5591 PUBCHEM_CID
6851 INN_ID
DB00197 DRUGBANK_ID
I66ZZ0ZN0E UNII
2693 IUPHAR_LIGAND_ID
203715 RXNORM
5640 MMSL
9149 MMSL
d04122 MMSL
006355 NDDF
109085002 SNOMEDCT_US
386967007 SNOMEDCT_US

Pharmaceutical products:

None