3605. Epalrestat

Nomenclature

CAS number: 82159-09-9
(5Z)-5-[(2E)-2-Methyl-3-phenyl-2-propenylidene]-4-oxo-2-thioxo-3-thiazolidineacetic acid; 5-[(E,E)-β-methylcinnamylidene]-4-oxo-2-thioxo-3-thiazolidineacetic acid; 3-carboxymethyl-5-(2-methylcinnamylidene)rhodanine; ONO-2235; Kinedak (Ono); Sorbistat (Ono).
C15H13NO3S2; mol wt 319.40.
C 56.41%, H 4.10%, N 4.39%, O 15.03%, S 20.08%.

Description and references

Aldose reductase inhibitor. Prepn: T. Tadao et al., EP 47109; eidem, US 4464382 (1982, 1984 both to Ono Pharmaceutical). Inhibitory effect on aldose reductase in vitro: H. Terashima et al., J. Pharmacol. Exp. Ther. 229, 226 (1983). Effect on motor nerve conduction and sorbitol levels in diabetic rats: R. Kikkawa et al., Diabetologia 24, 290 (1983). Effect in rats on peripheral nerve dysfunction: eidem, Metabolism 33, 212 (1984); on retinal microangiopathy: K. Kojima et al., Jpn. J. Ophthalmol. 29, 99 (1985).

Chemical structure

Properties

Crystals from ethanol-water, mp 210-217°.

Derivative

N-Methyl-d-glucamine salt.
C22H30N2O8S2; mol wt 514.61.
C 51.35%, H 5.88%, N 5.44%, O 24.87%, S 12.46%.

Properties

Crystals from methanol, mp 163-165°.

Therapeutic Category

Treatment of diabetic neuropathy.

Keywords

Aldose Reductase Inhibitor