9769. Troglitazone

Nomenclature

CAS number: 97322-87-7
5-[[4-[(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methoxy]phenyl]methyl]-2,4-thiazolidinedione; (±)-5-[4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl]-2,4-thiazolidinedione; romglizone; CS-045; CI-991; Noscal (Sankyo); Prelay (Sankyo); Rezulin.
C24H27NO5S; mol wt 441.54.
C 65.28%, H 6.16%, N 3.17%, O 18.12%, S 7.26%.

Description and references

Oral hypoglycemic agent which improves insulin sensitivity and decreases hepatic glucose production. Prepn: JP Kokai 85 51189; T. Yoshioka et al., US 4572912 (1985, 1986 both to Sankyo); T. Yoshioka et al., J. Med. Chem. 32, 421 (1989). Mechanism of action studies: T. P. Ciaraldi et al., Metabolism 39, 1056 (1990); M. Kellerer et al., Diabetes 43, 447 (1994). Clinical evaluation: T. Kuzuya et al., Diabetes Res. Clin. Pract. 11, 147 (1991). Clinical metabolic effects: S. L. Suter et al., Diabetes Care 15, 193 (1992).

Chemical structure

Properties

Crystals from benzene-acetone, mp 184-186°.

Therapeutic Category

Antidiabetic.

Keywords

Antidiabetic; Thiazolidinediones; Insulin Sensitizer