Structural Formula Vector Image
Title: Nateglinide
CAS Registry Number: 105816-04-4
CAS Name: N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-D-phenylalanine
Additional Names: (-)-N-(trans-4-isopropylcyclohexyl-1-carbonyl)-D-phenylalanine
Manufacturers' Codes: A-4166; AY-4166; SDZ-DJN-608; YM-026
Trademarks: Fastic (Ajinomoto); Starlix (Novartis); Starsis (Yamanouchi)
Molecular Formula: C19H27NO3
Molecular Weight: 317.42
Percent Composition: C 71.89%, H 8.57%, N 4.41%, O 15.12%
Literature 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).
Properties: Crystals from methanol-water, mp 129-130°. [a]D20 -9.4° (c = 1 in methanol). LD50 orally in rats: >2.0 g/kg (Hasegawa).
Melting point: mp 129-130°
Optical Rotation: [a]D20 -9.4° (c = 1 in methanol)
Toxicity data: LD50 orally in rats: >2.0 g/kg (Hasegawa)
Therap-Cat: Antidiabetic.
Keywords: Antidiabetic.

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