74259-08-8

Basic information

• Product Name: desacetyl-alacepril
• Synonyms: L-Phenylalanine,N-[1-(3-mercapto-2-methyl-1-oxopropyl)-L-prolyl]-, (S)-; DU 1227; Desacetylalacepril
• CAS NO: 74259-08-8
• Molecular Formula: C₁₈H₂₄N₂O₄S
• Molecular Weight: 364.45916
• Mol File: 74259-08-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 651.9°C at 760 mmHg
• Flash Point: 348.1°C
• Appearance: /
• Density: 1.268g/cm³
• Vapor Pressure: 6.97E-18mmHg at 25°C
• Refractive Index: 1.586
• CAS DataBase Reference: desacetyl-alacepril(CAS DataBase Reference)
• NIST Chemistry Reference: desacetyl-alacepril(74259-08-8)
• EPA Substance Registry System: desacetyl-alacepril(74259-08-8)

Safety Data

• Hazardous Substances Data: 74259-08-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H24N2O4S/c1-12(11-25)17(22)20-9-5-8-15(20)16(21)19-14(18(23)24)10-13-6-3-2-4-7-13/h2-4,6-7,12,14-15,25H,5,8-11H2,1H3,(H,19,21)(H,23,24)/t12-,14+,15+/m1/s1

Upstream product

• 74258-86-9 alacepril 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 129398-84-1 (S)-methyl 2-((S)-1-formylpyrrolidine-2-carbonylamino)-3-phenylpropanoate 
• 13200-83-4 (2S)-1-formylpyrrolidine-2-carboxylic acid 
• 147-85-3 L-proline 
• 13589-02-1 L-prolyl-L-phenylalanine 
• 1316643-70-5 C₃₈H₅₀N₄O₈S₂ 
• 74259-14-6 C₃₆H₄₆N₄O₈S₂ 
• 62571-86-2 captopril 
• 64806-05-9 Captopril disulfide 

Relevant articles and documents

Sialic acid 9-O-acetylesterase catalyzes the hydrolyzing reaction from alacepril to deacetylalacepril

Purpose. In this work, the alacepril thiolesterase, which catalyzes the hydrolyzing reaction of the thiolester linkage in alacepril and the conversion from alacepril to deacetylalacepril, was purified from rat liver cytosol and characterized. Methods. A purification procedure for the thiolesterase consisted of ammonium sulfate fractionation and chromatographies with phenyl Sepharose CL-4B, Q Sepharose FF, ceramic hydroxylapatite, and phenyl Sepharose HP. The thiolesterase activity was assayed for alacepril as a substrate and the reaction product, deacetylalacepril, was measured using high-performance liquid chromatography. Results. The purified thiolesterase is heterodimeric with a molecular mass of 29 and 36 kDa subunits as estimated by sodium dodecyl sulfate -polyacrylamide gel electrophoresis. N-terminal amino acid sequence of these subunits reveals that the thiolesterase is identical to sialic acid 9-O-acetylesterase. The thiolesterase hydrolyzes not only the thiolester bond in alacepril, spironolactone, and acetyl coenzyme A but also the carboxylester bond in α-naphtyl acetate. The alacepril thiolestrase activity is competitively inhibited by α-naphtyl acetate. Conclusion. The thiolesterase, i.e., sialic acid 9-O-acetylesterase, seems to be involved in the metabolism of certain drugs such as alacepril and spironolactone. However, drugs having ester-type and amide-type linkages, for example dilazep, aniracetam, and benazepril, are not substrates for the thiolestrase.

Synthesis of 1-((S)-3-acetylthio-2-methylpropanoyl)-L-pro pyl-L-phenylalanine (alacepril) and one of its active metabolites, the desacetyl derivative (DU-1227)

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