BRL

2,4-THIAZOLIDIINEDIONE, 5-[[4-[2-(METHYL-2-PYRIDINYLAMINO)ETHOXY]PHENYL]METHYL]-(9CL)

Created: 1999-07-08
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count44
Chiral Atom Count1
Bond Count46
Aromatic Bond Count12
2D diagram of BRL
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Chemical Component Summary

Name2,4-THIAZOLIDIINEDIONE, 5-[[4-[2-(METHYL-2-PYRIDINYLAMINO)ETHOXY]PHENYL]METHYL]-(9CL)
SynonymsBRL49653; ROSIGLITAZONE
Systematic Name (OpenEye OEToolkits)(5S)-5-[[4-[2-(methyl-pyridin-2-yl-amino)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
FormulaC18 H19 N3 O3 S
Molecular Weight357.427
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C1NC(=O)SC1Cc3ccc(OCCN(c2ncccc2)C)cc3
SMILESCACTVS3.341CN(CCOc1ccc(C[CH]2SC(=O)NC2=O)cc1)c3ccccn3
SMILESOpenEye OEToolkits1.5.0CN(CCOc1ccc(cc1)CC2C(=O)NC(=O)S2)c3ccccn3
Canonical SMILESCACTVS3.341 CN(CCOc1ccc(C[C@@H]2SC(=O)NC2=O)cc1)c3ccccn3
Canonical SMILESOpenEye OEToolkits1.5.0 CN(CCOc1ccc(cc1)C[C@H]2C(=O)NC(=O)S2)c3ccccn3
InChIInChI1.03 InChI=1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)/t15-/m0/s1
InChIKeyInChI1.03 YASAKCUCGLMORW-HNNXBMFYSA-N

Drug Info: DrugBank

DrugBank IDDB00412 
NameRosiglitazone
Groups
  • approved
  • investigational
DescriptionRosiglitazone is an anti-diabetic drug in the thiazolidinedione class of drugs. It is marketed by the pharmaceutical company GlaxoSmithKline as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Like other thiazolidinediones, the mechanism of action of rosiglitazone is by activation of the intracellular receptor class of the peroxisome proliferator-activated receptors (PPARs), specifically PPARγ. Rosiglitazone is a selective ligand of PPARγ, and has no PPARα-binding action. Apart from its effect on insulin resistance, it appears to have an anti-inflammatory effect: nuclear factor kappa-B (NFκB) levels fall and inhibitor (IκB) levels increase in patients on rosiglitazone. Recent research has suggested that rosiglitazone may also be of benefit to a subset of patients with Alzheimer's disease not expressing the ApoE4 allele. This is the subject of a clinical trial currently underway.
Synonyms
  • (RS)-5-{4-[2-(Methyl-2-pyridylamino)ethoxy]benzyl}-2,4-thiazolidinedion
  • Rosiglitazone
  • Rosiglitazon
  • Rosiglitazonum
  • Rosiglitazona
Brand Names
  • Avaglim
  • Avandia 4mg
  • Mylan-rosiglitazone
  • Dom-rosiglitazone
  • PHL-rosiglitazone
IndicationRosiglitazone is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus.
Categories
  • Alimentary Tract and Metabolism
  • Blood Glucose Lowering Agents
  • BSEP/ABCB11 Substrates
  • Cytochrome P-450 CYP1A2 Inhibitors
  • Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
ATC-Code
  • A10BD04
  • A10BG02
  • A10BD03
CAS number122320-73-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Peroxisome proliferator-activated receptor gammaMGETLGDSPIDPESDSFTDTLSANISQEMTMVDTEMPFWPTNFGISSVDL...unknownagonist
Long-chain-fatty-acid--CoA ligase 4MKLKLNVLTIILLPVHLLITIYSALIFIPWYFLTNAKKKNAMAKRIKAKP...unknowninhibitor
Peroxisome proliferator-activated receptor alphaMVDTESPLCPLSPLEAGDLESPLSEEFLQEMGNIQEISQSIGEDSSGSFG...unknown
Peroxisome proliferator-activated receptor deltaMEQPQEEAPEVREEEEKEEVAEAEGAPELNGGPQHALPSSSYTDLSRSSS...unknown
Retinoic acid receptor RXR-alphaMDTKHFLPLDFSTQVNSSLTSPTGRGSMAAPSLHPSLGPGIGSPGQLHSP...unknown
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL121106
PubChem 445655
ChEMBL CHEMBL121106
ChEBI CHEBI:50125
CCDC/CSD KIWVUI