Darglitazone

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	141200-24-0
PubChem (CID)	60870
ChemSpider	54854
UNII	AVP9C03Z3K
ChEMBL	CHEMBL55624
Chemical and physical data
Formula	C23H20N2O4S
Molar mass	420.481 g/mol
3D model (Jmol)	Interactive image
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) Key:QQKNSPHAFATFNQ-UHFFFAOYSA-N
(what is this?)  (verify)

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]

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

Synthesis

Synthesis of darglitazone

References

1. Hulin, Bernard; Clark, David A.; Goldstein, Steven W.; McDermott, Ruth E.; Dambek, Paul J.; Kappeler, Werner H.; Lamphere, Charles H.; Lewis, Diana M.; Rizzi, James P. (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". AdisInsight. Adis International Ltd, part of Springer Science+Business Media. Retrieved 28 November 2015.