Alacepril

Title: Alacepril
CAS Registry Number: 74258-86-9
CAS Name: 1-[(2S)-3-(Acetylthio)-2-methyl-1-oxopropyl]-L-prolyl-L-phenylalanine
Additional Names: 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.
Alachlor Alafosfalin Alagebrium Chloride Alanine Alantolactone

Alacepril
Alacepril.png
Systematic (IUPAC) name
(2S)-2-([(2S)-1-[(2S)-3-acetylsulfanyl-2-methylpropanoyl]pyrrolidine-2-carbonyl]amino)-3-phenylpropanoic acid
Clinical data
AHFS/Drugs.com International Drug Names
Legal status Prescription only
Routes Oral
Identifiers
CAS number 74258-86-9 N
ATC code None
PubChem CID 71992
ChemSpider 64993 YesY
UNII X39TL7JDPF YesY
KEGG D01900 YesY
Chemical data
Formula C20H26N2O5S 
Mol. mass 406.49 g/mol
 N (what is this?)  (verify)

Alacepril (INN) is an ACE inhibitor.