7452. Pioglitazone
Nomenclature
CAS number: 111025-46-8
5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione; (±)-5-[p-[2-(ethyl-2-pyridyl)ethoxy]benzyl]-2,4-thiazolidinedione; AD-4833. C19H20N2O3S; mol wt 356.44.
C 64.02%, H 5.66%, N 7.86%, O 13.47%, S 9.00%.
Description and references
Insulin sensitizer. Prepn: K. Meguro, T. Fujita, EP 193256; eidem, US 4687777 (1986, 1987 both to Takeda); T. Sohda et al., Arzneim.-Forsch. 40, 37 (1990). Pharmacology: H. Ikeda et al., ibid. 156. HPLC determn in serum: W. Z. Zhong, D. B. Lakings, J. Chromatogr. 490, 377 (1989). Mechanism of action: C. Hofmann et al., Endocrinology 129, 1915 (1991); M. Kobayashi et al., Diabetes 41, 476 (1992). Effect on adipocyte differentiation: T. Sandouk et al., Am. J. Physiol. 264, C1600 (1993). Clinical evaluation in noninsulin-dependent diabetes: R. Kawamori et al., Diabetes Res. Clin. Pract. 41, 35 (1998).
Properties
Colorless needles from DMF + water, mp 183-184°.Derivative
Hydrochloride.Nomenclature
CAS number: 112529-15-4
U-72107A; Actos (Takeda). C19H20N2O3S.HCl; mol wt 392.90.
C 58.08%, H 5.39%, N 7.13%, O 12.22%, S 8.16%, Cl 9.02%.
Properties
Colorless prisms from ethanol, mp 193-194°. Sol in DMF; slightly sol in ethanol; very slightly sol in acetone, acetonitrile. Practically insol in water; insol in ether.Therapeutic Category
Antidiabetic.
Keywords
Antidiabetic; Thiazolidinediones; Insulin Sensitizer