Darglitazone

Darglitazone (previously known as CP 86325-2) is a member of the thiazolidinedione class of drugs and an agonist of peroxisome proliferator-activated receptor-γ (PPAR-γ), an orphan member of the nuclear receptor superfamily of transcription factors. It has a variety of insulin-sensitizing effects, such as improving glycemic and lipidemic control, and was researched by Pfizer as a treatment of metabolic disorders such as type 2 diabetes mellitus.[1]

Darglitazone
Legal status
Legal status
  • Development terminated
Identifiers
IUPAC name
  • 5-[(4-[3-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)propanoyl]phenyl)methyl]-1,3-thiazolidine-2,4-dione
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H20N2O4S
Molar mass420.48 g·mol−1
3D model (JSmol)
SMILES
  • CC1=C(N=C(O1)C2=CC=CC=C2)CCC(=O)C3=CC=C(C=C3)CC4C(=O)NC(=O)S4
InChI
  • InChI=1S/C23H20N2O4S/c1-14-18(24-22(29-14)17-5-3-2-4-6-17)11-12-19(26)16-9-7-15(8-10-16)13-20-21(27)25-23(28)30-20/h2-10,20H,11-13H2,1H3,(H,25,27,28) N
  • Key:QQKNSPHAFATFNQ-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

Its development was terminated on November 08, 1999.[2]

Synthesis
Synthesis of darglitazone







References
  1. Hulin B, Clark DA, Goldstein SW, McDermott RE, Dambek PJ, Kappeler WH, et al. (May 1992). "Novel thiazolidine-2,4-diones as potent euglycemic agents". Journal of Medicinal Chemistry. 35 (10): 1853–64. doi:10.1021/jm00088a022. PMID 1588563.
  2. "Drug Profile: Darglitazone". Adis Insight. Springer Nature Switzerland AG. Retrieved 28 November 2015.
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