Title: Alacepril
CAS Registry Number: 74258-86-9
CAS Name: 1-[(2
S)-3-(Acetylthio)-2-methyl-1-oxopropyl]-L-prolyl-L-phenylalanine
Synonyms: 1-(D-3-acetylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine;
N-[1-[
(S)-3-mercapto-2-methylpropionyl]-L-prolyl]-3-phenyl-L-alanine acetate (ester)
Manufacturers' Codes: DU-1219
Trademarks: Cetapril (Dainippon)
Molecular Formula: C20H26N2O5S
Molecular Weight: 406.50
Percent Composition: C 59.09%, H 6.45%, N 6.89%, O 19.68%, S 7.89%
Literature References: Angiotensin-converting enzyme (ACE) inhibitor. Prepn: T. Sawayama
et al., JP Kokai 80 9058;
eidem, US 4248883 (1980, 1981 both to Dainippon Pharm.). Pharmacology in animals: K. Takeyama
et al., Arzneim.-Forsch. 35, 1502 (1985);
eidem, ibid. 1507. Series of articles on pharmacology, metabolism, enzyme inhibiting activity:
ibid. 36, 47-83 (1986). Metabolism to captopril,
q.v.: K. Matsumoto
et al., ibid. 40. HPLC determn of metabolites in plasma and urine: K. Hayashi
et al., J. Chromatogr. 338, 161 (1985). Pharmacokinetics in humans: K. Onoyama
et al., Clin. Pharmacol. 38, 462 (1985). Preclinical evaluation in essential hypertension: K. Mizuno
et al., Res. Commun. Chem. Pathol. Pharmacol. 49, 175 (1985); H. Shionoiri
et al., Curr. Ther. Res. 38, 537 (1985). Series of articles on toxicology: M. Iida
et al., Yakuri to Chiryo 13, 7033-7121 (1985),
C.A. 104, 21888h-21890c;
105, 396v (1986).
Properties: Crystals from ethanol/
n-hexane, mp 155-156°. [a]D25 -81.3° (c = 1.02 in ethanol). LD50 in rats, mice (mg/kg): >5000, >5000 orally; >3000, >3000 s.c.; ~2000, ~3000 i.p. (Iida, pp 7033-40).
Melting point: mp 155-156°
Optical Rotation: [a]D25 -81.3° (c = 1.02 in ethanol)
Toxicity data: LD50 in rats, mice (mg/kg): >5000, >5000 orally; >3000, >3000 s.c.; ~2000, ~3000 i.p. (Iida, pp 7033-40)
Therap-Cat: Antihypertensive.
Keywords: ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives.
