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{{short description|Chemical compound}}
{{Drugbox {{Drugbox
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Revision as of 12:26, 3 January 2023

Chemical compound Pharmaceutical compound
Darglitazone
Legal status
Legal status
  • Development terminated
Identifiers
IUPAC name
  • 5-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
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)
  • 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.

Its development was terminated on November 08, 1999.

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.
Oral diabetes medication, insulins and insulin analogs, and other drugs used in diabetes (A10)
Insulins / insulin analogs
fast-acting
short-acting
long-acting
ultra-long-acting
inhalable
  • Exubera
  • Afrezza
Non-insulins
Insulin sensitizers
Biguanides
TZDs/"glitazones" (PPAR)
Dual PPAR agonists
Amylin analogs and DACRAs
Secretagogues
KATP
Sulfonylureas
Meglitinides/"glinides"
GLP-1 receptor agonists
GLP1 poly-agonist peptides
DPP-4 inhibitors/"gliptins"
Other
Aldose reductase inhibitors
Alpha-glucosidase inhibitors
SGLT2 inhibitors/"gliflozins"
Other
Combinations
PPARTooltip Peroxisome proliferator-activated receptor modulators
PPARαTooltip Peroxisome proliferator-activated receptor alpha
PPARδTooltip Peroxisome proliferator-activated receptor delta
PPARγTooltip Peroxisome proliferator-activated receptor gamma
Non-selective
See also
Receptor/signaling modulators
Categories: