7170. Perindopril

Nomenclature

CAS number: 82834-16-0
(2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)butyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic acid; (2S,3aS,7aS)-1-[(S)-N-[(S)-1-carboxybutyl]alanyl]hexahydro-2-indolinecarboxylic acid 1-ethyl ester; (2S)-2-[(1S)-1-carbethoxybutylamino]-1-oxopropyl-(2S,3aS,7aS)-perhydroindole-2-carboxylic acid; S-9490; McN-A-2833.
C19H32N2O5; mol wt 368.47.
C 61.93%, H 8.75%, N 7.60%, O 21.71%.

Description and references

Angiotensin-converting enzyme (ACE) inhibitor. Hydrolyzed in vivo to the active diacid metabolite. Prepn: G. Remond et al., EP 49658 (1982 to Sci. Union et Cie. - Soc. Franc. Rech. Med.); M. Vincent et al., US 4508729 (1985 to ADIR). Stereoselective synthesis: M. Vincent et al., Tetrahedron Lett. 23, 1677 (1982). NMR study: N. Platzer et al., Magn. Reson. Chem. 26, 296 (1988). Hemodynamic effects in humans: K. R. Lees, J. L. Reid, Br. J. Clin. Pharmacol. 23, 159 (1987). Clinical evaluation in essential hypertension: T. Morgan et al., J. Cardiovasc. Pharmacol. 10, Suppl. 7, S116 (1987). Pharmacokinetics, pharmacodynamics of the diacid: K. R. Lees, J. L. Reid, ibid. 10, 129 (1987). Review of pharmacology and clinical use: P. A. Todd, A. Fitton, Drugs 42, 90-114 (1991). Symposium on clinical efficacy in cardiovascular disease: Am. J. Cardiol. 88, Suppl. 1, 1-40 (2001).

Chemical structure

Derivative

tert-Butylamine.

Nomenclature

CAS number: 107133-36-8
Perindopril erbumine; S-9490-3; McN-A-2833-109; Aceon (Solvay); Coversum (Servier); Coversyl (Servier); Procaptan (Stroder).
C19H32N2O5.C4H11N; mol wt 441.60.
C 62.56%, H 9.81%, N 9.52%, O 18.12%.

Derivative

Diacid form.

Nomenclature

CAS number: 95153-31-4
Perindoprilat; S-9780.
C17H28N2O5; mol wt 340.41.
C 59.98%, H 8.29%, N 8.23%, O 23.50%.

Therapeutic Category

Antihypertensive.

Keywords

ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives