Zofenopril
Title: Zofenopril
CAS Registry Number: 81872-10-8
CAS Name: (4S)-1-[(2S)-3-(Benzoylthio)-2-methyl-1-oxopropyl]-4-(phenylthio)-L-proline
Additional Names: [1(S),4(S)]-1-(3-mercapto-2-methyl-1-oxopropyl)-4-phenyl-thio-L-proline-S-benzoylester
Molecular Formula: C22H23NO4S2
Molecular Weight: 429.55
Percent Composition: C 61.51%, H 5.40%, N 3.26%, O 14.90%, S 14.93%
Literature References: Angiotensin-converting enzyme (ACE) inhibitor; de-esterified in vivo to its active sulfhydryl-containing metabolite, zofenoprilat. Prepn: M. A. Ondetti, J. Krapcho, GB 2028327; eidem, US 4316906 (1980, 1982 both to E. R. Squibb & Sons). LC/MS/MS determn in plasma: L. Dal Bo et al., J. Chromatogr. B 749, 287 (2000). Role of sulfhydryl group in improvement of endothelial dysfunction: H. Buikema et al., Br. J. Pharmacol. 130, 1999 (2000); L. Cominacini et al., Am. J. Hypertens. 15, 891 (2002). Clinical comparison with lisinopril of effect on post-infarction survival: C. Borghi, E. Ambrosioni, Am. Heart J. 145, 80 (2003). Review of properties and pharmacokinetics: A. Subissi et al., Cardiovasc. Drug Rev. 17, 115-133 (1999); of clinical efficacy in cardiovascular diseases: C. Borghi et al., Expert Opin. Pharmacother. 5, 1965-1977 (2004).
Properties: Foamy solid, mp 42-44°. [a]D25 -36.5° (c = 1 in methanol).
Melting point: mp 42-44°
Optical Rotation: [a]D25 -36.5° (c = 1 in methanol)
 
Derivative Type: Calcium salt
CAS Registry Number: 81938-43-4
Manufacturers' Codes: MEN-8029; SQ-26991
Trademarks: Bifril (Menarini); Zofenil (Menarini)
Molecular Formula: C44H44CaN2O8S4
Molecular Weight: 897.17
Percent Composition: C 58.90%, H 4.94%, Ca 4.47%, N 3.12%, O 14.27%, S 14.30%
Properties: White crystalline powder, mp >250°. [a]D23 -67.6° (c = 1 in methanol/HCl). Partition coefficient (octanol/water): 3.5.
Melting point: mp >250°
Optical Rotation: [a]D23 -67.6° (c = 1 in methanol/HCl)
Log P: Partition coefficient (octanol/water): 3.5
 
Therap-Cat: Antihypertensive.
Keywords: ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives.

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