Fosinopril

Fosinopril
Clinical data
Trade names	Monopril
AHFS/Drugs.com	Monograph
MedlinePlus	a692020
Pregnancy; category	AU: D; ;
Routes of; administration	By mouth
ATC code	C09AA09 (WHO) ;
Legal status
Legal status	US: WARNING; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	~36%
Protein binding	87% (fosinoprilat)
Metabolism	liver, GIT mucosa (to fosinoprilat)
Elimination half-life	12 hours (fosinoprilat)
Excretion	kidney
Identifiers
	IUPAC name (2S,4S)-4-cyclohexyl-1-[2-[hydroxy(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid;
CAS Number	98048-97-6 ;
PubChem CID	55891;
IUPHAR/BPS	6456;
DrugBank	DB00492 ;
ChemSpider	10482016 ;
UNII	R43D2573WO;
KEGG	D07992 ;
ChEMBL	ChEMBL3039598 ;
CompTox Dashboard (EPA)	DTXSID1023079 ;
Chemical and physical data
Formula	C30H46NO7P
Molar mass	563.672 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(CP(=O)(CCCCc1ccccc1)OC(OC(=O)CC)C(C)C)N2C[C@@H](C[C@H]2C(O)=O)C3CCCCC3;
	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 ; Key:BIDNLKIUORFRQP-YYTCENNOSA-N ;
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Fosinopril is an angiotensin converting enzyme (ACE) inhibitor^[2] used for the treatment of hypertension and some types of chronic heart failure. Fosinopril is the only phosphonate-containing ACE inhibitor marketed, by Bristol-Myers Squibb under the trade name Monopril. Fosinopril is a cascading pro-drug. The special niche for the medication that differentiates it from the other members of the ACE Inhibitor drug class is that was specifically developed for the use for patients with renal impairment. This was through manipulation of the metabolism and excretion, and is seen that fifty percent of the drug is hepatobiliary cleared, which can compensate for diminished renal clearance. The remaining fifty percent is excreted in urine. It does not need dose adjustment.

It was patented in 1980 and approved for medical use in 1991.^[3]

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ 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): 1303–1311. doi:10.1503/cmaj.060068. PMC 2335176. PMID 18458262.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 468. ISBN 9783527607495.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[pmid18458262-2] 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): 1303–1311. doi:10.1503/cmaj.060068. PMC 2335176. PMID 18458262.

[Fis2006-3] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 468. ISBN 9783527607495.

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