Fosinopril

Fosinopril

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 Y
ATC code	C09AA09
PubChem	CID 55891
DrugBank	APRD00526
ChemSpider	10482016 Y
UNII	R43D2573WO Y
KEGG	D07992 N
ChEMBL	CHEMBL1201310 N
Chemical data
Formula	C30H46NO7P
Mol. mass	563.663 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C30H46NO7P/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35)/t25-,26+,30?,39-/m1/s1 Y Key:BIDNLKIUORFRQP-YYTCENNOSA-N Y
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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.

Fosinoprilat and Fosinopril

Fosinoprilat proved to have the same problem as enalaprilat and the other carboxylate-containing ACE inhibitors (namely poor oral bioavailability). Addition of a hydrophobic side-chain modulated the ionisation characteristics of the molecule making it more bioavailable. Fosinopril is administered as a prodrug and is converted in vivo to the active form fosinoprilat.

References

1. ^ Pilote L, Abrahamowicz M, Eisenberg M, Humphries K, Behlouli H, Tu JV (May 2008). "Effect of different angiotensin-converting-enzyme inhibitors on mortality among elderly patients with congestive heart failure". CMAJ 178 (10): 1303–11. doi:10.1503/cmaj.060068. PMC 2335176. PMID 18458262. http://www.cmaj.ca/cgi/pmidlookup?view=long&pmid=18458262.