8136. Repaglinide

Nomenclature

CAS number: 135062-02-1
2-Ethoxy-4-[2-[[(1S)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid; (+)-2-ethoxy-α-[[(S)-α-isobutyl-o-piperidinobenzyl]carbamoyl]-p-toluic acid; (S)-(+)-2-ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoic acid; AG-EE-623 ZW; Novonorm (Novo Nordisk); Prandin (Novo Nordisk).
C27H36N2O4; mol wt 452.59.
C 71.65%, H 8.02%, N 6.19%, O 14.14%.

Description and references

Non-sulfonylurea oral hypoglycemic agent. Prepn: W. Grell et al., WO 9300337 (1993 to Thomae). HPLC determn of racemate in human plasma: A. Greischel et al., J. Chromatogr. 568, 246 (1991). Clinical pharmacokinetics: F. J. Ampudia-Blasco et al., Diabetologia 37, 703 (1994). Comparative clinical evaluation in NIDDM: B. H. R. Wolffenbuttel et al., Eur. J. Clin. Pharmacol. 45, 113 (1993).

Chemical structure

Properties

White, odorless, crystalline powder. Crystals from ethanol/water (2:1), mp 126-128°. Crystals from neutralized water, mp 130-131°. [α]D20 +6.97° (c = 0.975 in methanol); [α]D20 +7.45° (c = 1.06 in methanol). LD50 orally in rats: >1 g/kg (Grell).

Therapeutic Category

Antidiabetic.

Keywords

Antidiabetic