Fasidotril

Title: Fasidotril
CAS Registry Number: 135038-57-2
CAS Name: N-[(2S)-3-(Acetylthio)-2-(1,3-benzodioxol-5-ylmethyl)-1-oxopropyl]-L-alanine phenylmethyl ester
Additional Names: N-[(S)-a-(mercaptomethyl)-3,4-(methylenedioxy)-hydrocinnamoyl]-L-alanine, benzyl ester acetate (ester); aladotril; alatriopril
Manufacturers' Codes: BP-1137
Molecular Formula: C23H25NO6S
Molecular Weight: 443.51
Percent Composition: C 62.29%, H 5.68%, N 3.16%, O 21.64%, S 7.23%
Literature References: Vasopeptidase inhibitor (VPI) exhibiting characteristic dual metalloprotease inhibition of neutral endopeptidase (NEP) and angiotensin converting enzyme (ACE). Prepn: J.-C. Plaquevent et al., EP 419327; eidem, US 5670531 (1991, 1997 both to Soc. Civile Bioprojet). Absolute configuration: V. Grosset et al., Tetrahedron: Asymmetry 14, 2335 (2003). Enzyme inhibition activity: C. Gros et al., Proc. Natl. Acad. Sci. USA 88, 4210 (1991). Preclinical and clinical pharmacology: S. Laurent et al., Hypertension 35, 1148 (2000). Review of design and pharmacology: J. Bralet et al., Cardiovasc. Drug Rev. 18, 1-24 (2000); of therapeutic potential: F. Ozdener, V. Ozdemir, Curr. Opin. Invest. Drugs 4, 1113-1119 (2003).
Properties: mp 104°. [a]D25 -50.6° (c = 1.35 in methanol). Also reported as white to yellowish microcrystalline powder, mp 108° (Bralet). Sol in acetone, chloroform, dimethylformamide. Nearly insol in water.
Melting point: mp 104°; mp 108° (Bralet)
Optical Rotation: [a]D25 -50.6° (c = 1.35 in methanol)
Derivative Type: Diacid
CAS Registry Number: 135038-59-4
Additional Names: Alatrioprilat; fasidotrilat
Molecular Formula: C14H17NO5S
Molecular Weight: 311.35
Percent Composition: C 54.01%, H 5.50%, N 4.50%, O 25.69%, S 10.30%
Properties: Biologically active metabolite. [a]D25 +12.9° (c = 1.3 in methanol).
Optical Rotation: [a]D25 +12.9° (c = 1.3 in methanol)
Therap-Cat: Antihypertensive.
Keywords: Antihypertensive; Vasopeptidase Inhibitor.
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