3940. Fasidotril

Nomenclature

CAS number: 135038-57-2
N-[(2S)-3-(Acetylthio)-2-(1,3-benzodioxol-5-ylmethyl)-1-oxopropyl]-l-alanine phenylmethyl ester; N-[(S)-α-(mercaptomethyl)-3,4-(methylenedioxy)-hydrocinnamoyl]-l-alanine, benzyl ester acetate (ester); aladotril; alatriopril; BP-1137.
C23H25NO6S; mol wt 443.51.
C 62.29%, H 5.68%, N 3.16%, O 21.64%, S 7.23%.

Description and 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. Investig. Drugs 4, 1113-1119 (2003).

Chemical structure

Properties

mp 104°. [α]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.

Derivative

Diacid.

Nomenclature

CAS number: 135038-59-4
Alatrioprilat; fasidotrilat.
C14H17NO5S; mol wt 311.35.
C 54.01%, H 5.50%, N 4.50%, O 25.69%, S 10.30%.

Properties

Biologically active metabolite. [α]D25 +12.9° (c = 1.3 in methanol).

Therapeutic Category

Antihypertensive.

Keywords

Antihypertensive; Vasopeptidase Inhibitor