4256. Fosinopril

Nomenclature

CAS number: 98048-97-6
(4S)-4-Cyclohexyl-1-[[(R)-[(1S)-2-methyl-1-(1-oxopropoxy)propoxy](4-phenylbutyl)phosphinyl]acetyl]-l-proline; (4S)-4-cyclohexyl-1-[[[(RS)-1-hydroxy-2-methylpropoxy](4-phenylbutyl)phosphinyl]acetyl]-l-proline propionate (ester); fosenopril.
C30H46NO7P; mol wt 563.66.
C 63.93%, H 8.23%, N 2.48%, O 19.87%, P 5.50%.

Description and references

Phosphinic acid containing angiotensin converting enzyme (ACE) inhibitor. Prepn: E. W. Petrillo, Jr., US 4337201 (1982 to Squibb); of active diacid form: J. Krapcho et al., J. Med. Chem. 31, 1148 (1988). Metabolism and pharmacokinetics: S. M. Singhvi et al., Br. J. Clin. Pharmacol. 25, 9 (1988). GC determn of diacid: M. Jemal et al., J. Chromatogr. 345, 299 (1985). Clinical trial in hypertension: P. A. Sullivan et al., Am. J. Hypertens. 1, 280S (1988). Brief description: E. W. Petrillo, Jr., et al., Clin. Exp. Theory Prac. A9, 235 (1987). Series of articles on pharmacology, pharmacokinetics, and clinical experience: Drug Invest. 3, Suppl. 4, 1-53 (1991).

Chemical structure

Derivative

Sodium salt.

Nomenclature

CAS number: 88889-14-9
SQ-28555; Dynacil (Schwarz); Elidiur (BMS); Fosinorm (BMS); Fositen (BMS); Fozitec (Lipha); Monopril (BMS); Staril (BMS); Tensozide (Mead Johnson).
C30H45NNaO7P; mol wt 585.64.
C 61.53%, H 7.74%, N 2.39%, Na 3.93%, O 19.12%, P 5.29%.

Derivative

Diacid.

Nomenclature

CAS number: 95399-71-6
SQ-27519.
C23H34NO5P; mol wt 435.49.
C 63.43%, H 7.87%, N 3.22%, O 18.37%, P 7.11%.

Properties

mp 149-153°. [α]D 24° (c = 1 in methanol).

Therapeutic Category

Antihypertensive.

Keywords

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