6428. Nateglinide

Nomenclature

CAS number: 105816-04-4
N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-d-phenylalanine; (-)-N-(trans-4-isopropylcyclohexyl-1-carbonyl)-d-phenylalanine; A-4166; AY-4166; SDZ-DJN-608; YM-026; Fastic (Ajinomoto); Starlix (Novartis); Starsis (Yamanouchi).
C19H27NO3; mol wt 317.42.
C 71.89%, H 8.57%, N 4.41%, O 15.12%.

Description and references

Amino acid derivative that stimulates insulin secretion. Prepn: S. Toyoshima et al., EP 196222; eidem, US 4816484 (1986, 1989 both to Ajinomoto); H. Shinkai et al., J. Med. Chem. 32, 1436 (1989). Effect on insulin secretion: Y. Sato et al., Diabetes Res. Clin. Pract. 12, 53 (1991). HPLC determn in plasma and urine: I. Ono et al., J. Chromatogr. B 692, 397 (1997). Series of articles on pharmacology, pharmacokinetics and toxicology: Yakuri to Chiryo 25, Suppl. 1, S9-S239 (1997). Toxicity data: K. Hasegawa et al., ibid. S5, C.A. 126, 152622 (1997).

Chemical structure

Properties

Crystals from methanol-water, mp 129-130°. [α]D20 -9.4° (c = 1 in methanol). LD50 orally in rats: >2.0 g/kg (Hasegawa).

Therapeutic Category

Antidiabetic.

Keywords

Antidiabetic