Structure via PubChem · Public domain (PubChem)
fosinopril
Sign in to saveAlso known as (S)-4-cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid, (2S,4S)-4-cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid, (2S,4S)-4-cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid
Fosinopril is an angiotensin converting enzyme (ACE) inhibitor 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 t
In the Vinony graph
Within Vinony's link graph, fosinopril is referenced by 141 other articles, and connects out to angiotensins, amlodipine/valsartan and liver.
It is catalogued under topics including ACE inhibitors, Carboxamides and Cyclohexyl compounds.
Its subject is documented across 25 Wikipedia language editions.
Chemical data
- Formula
- C30H46NO7P
- Molecular weight
- 563.7 g/mol
- IUPAC name
- (2S,4S)-4-cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid
- SMILES
- CCC(=O)OC(C(C)C)OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N2C[C@@H](C[C@H]2C(=O)O)C3CCCCC3
- InChIKey
- BIDNLKIUORFRQP-FKDWWROVSA-N
- XLogP
- 6.2
- Polar surface area
- 110 Ų
- H-bond donors
- 1
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
658 papers- Fosinopril.2006
- Fosinopril.2012
- Fosinopril.2026
- Fosinopril. Clinical pharmacokinetics and clinical potential.Clinical pharmacokinetics · 1997
- Fosinopril. A review of its pharmacology and clinical efficacy in the management of heart failure.Drugs · 1997
via PubMed
Wikidata facts
- Subclass of
- phosphinate ester
- Has part
- carbon
- Mass
- 563.301189
- Has use
- medication
Show 10 more facts
- defined daily dose
- 15
- NCI Thesaurus ID
- C65761
- chemical formula
- C₃₀H₄₆NO₇P
- medical condition treated
- arterial hypertension
- canonical SMILES
- CCC(=O)OC(C(C)C)OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N2CC(CC2C(=O)O)C3CCCCC3
- subject has role
- antihypertensive drug
- Commons category
- Fosinopril
- significant drug interaction
- furosemide
- legal status (medicine)
- boxed warning
- isomeric SMILES
- CCC(=O)OC(OP(=O)(CCCCc1ccccc1)CC(=O)N1C[C@H](C2CCCCC2)C[C@H]1C(=O)O)C(C)C
via Wikidata · CC0
~3 min read
Encyclopedic overview
3 sectionsContents
- Medical uses
- Chemistry
- References
Fosinopril is an angiotensin converting enzyme (ACE) inhibitor 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.
Excerpted from Wikipedia’s “fosinopril” article, available under the CC BY-SA 4.0 licence.