Fosinopril

Title: Fosinopril
CAS Registry Number: 98048-97-6
CAS Name: (4S)-4-Cyclohexyl-1-[[(R)-[(1S)-2-methyl-1-(1-oxopropoxy)propoxy](4-phenylbutyl)phosphinyl]acetyl]-L-proline
Additional Names: (4S)-4-cyclohexyl-1-[[[(RS)-1-hydroxy-2-methylpropoxy](4-phenylbutyl)phosphinyl]acetyl]-L-proline propionate (ester); fosenopril
Molecular Formula: C30H46NO7P
Molecular Weight: 563.66
Percent Composition: C 63.93%, H 8.23%, N 2.48%, O 19.87%, P 5.50%
Literature 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).
Derivative Type: Sodium salt
CAS Registry Number: 88889-14-9
Manufacturers' Codes: SQ-28555
Trademarks: Dynacil (Schwarz); Elidiur (BMS); Fosinorm (BMS); Fositen (BMS); Fozitec (Lipha); Monopril (BMS); Staril (BMS); Tensozide (Mead Johnson)
Molecular Formula: C30H45NNaO7P
Molecular Weight: 585.64
Percent Composition: C 61.53%, H 7.74%, N 2.39%, Na 3.93%, O 19.12%, P 5.29%
Derivative Type: Diacid
CAS Registry Number: 95399-71-6
Manufacturers' Codes: SQ-27519
Molecular Formula: C23H34NO5P
Molecular Weight: 435.49
Percent Composition: C 63.43%, H 7.87%, N 3.22%, O 18.37%, P 7.11%
Properties: mp 149-153°. [a]D -24° (c = 1 in methanol).
Melting point: mp 149-153°
Optical Rotation: [a]D -24° (c = 1 in methanol)
Therap-Cat: Antihypertensive.
Keywords: ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives.
Fosmidomycin Fosphenytoin Fospirate Fospropofol Fosthiazate

Fosinopril
Fosinopril CASCC.png
Systematic (IUPAC) name
(2S,4S)-4-cyclohexyl-1-(2-{[2-methyl-1-(propanoyloxy)propoxy](4-phenylbutyl)phosphoryl}acetyl)pyrrolidine-2-carboxylic acid
Clinical data
Trade names Monopril
AHFS/Drugs.com monograph
MedlinePlus a692020
Pregnancy cat. D (AU)
Legal status Prescription only
Routes oral
Pharmacokinetic data
Bioavailability ~36%
Protein binding 87% (fosinoprilat)
Metabolism hepatic, GIT mucosa (to fosinoprilat)
Half-life 12 hours (fosinoprilat)
Excretion renal
Identifiers
CAS number 98048-97-6 YesY
ATC code C09AA09
PubChem CID 55891
DrugBank DB00492
ChemSpider 10482016 YesY
UNII R43D2573WO YesY
KEGG D07992 YesY
ChEMBL CHEMBL1201310 N
Chemical data
Formula C30H46NO7P 
Mol. mass 563.663 g/mol
 N (what is this?)  (verify)

Fosinopril is an angiotensin converting enzyme (ACE) inhibitor[1] used for the treatment of hypertension and some types of chronic heart failure. Fosinopril is the only phosphinate-containing ACE inhibitor marketed. It is marketed by Bristol-Myers Squibb under the trade name Monopril.

Fosinoprilat, the active form of fosinopril.