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Darglitazone

Legal status
Legal status	Development terminated
Identifiers
IUPAC name 5-phenyl)methyl]-1,3-thiazolidine-2,4-dione
CAS Number	141200-24-0
PubChem CID	60870
ChemSpider	54854
UNII	AVP9C03Z3K
ChEMBL	ChEMBL55624
CompTox Dashboard (EPA)	DTXSID3057644
Chemical and physical data
Formula	C23H20N2O4S
Molar mass	420.48 g·mol
3D model (JSmol)	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
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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.

Its development was terminated on November 08, 1999.

Synthesis

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.

• Abandoned drugs
• Oxazoles
• Thiazolidinediones