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Fosinopril
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| Systematic (IUPAC) name | |
| 4-cyclohexyl-1-[2-[(2-methyl-1-propanoyloxy-propoxy)-(4-phenylbutyl)phosphoryl]acetyl] -pyrrolidine-2-carboxylic acid (Diagrams above are fosinopril and fosinoprilat, respectively. Data below refers to fosinopril unless indicated) |
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| Identifiers | |
| CAS number | |
| ATC code | C09 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C30H46NO7P |
| Mol. mass | 563.663 g/mol |
| Pharmacokinetic data | |
| Bioavailability | ~36% |
| Protein binding | 87% (fosinoprilat) |
| Metabolism | hepatic, GIT mucosa (to fosinoprilat) |
| Half life | 12 hours (fosinoprilat) |
| Excretion | renal |
| Therapeutic considerations | |
| Pregnancy cat. |
D(AU) |
| Legal status |
℞ Prescription only |
| Routes | oral |
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. It is marketed by Bristol-Myers Squibb under the trade name Monopril.
Fosinoprilat and Fosinopril
Fosinoprilat proved to have the same problem as enalaprilat and the other carboxylate-containing ACE inhibitors (namely poor oral bioavailability). The solution, fortunately, was very similar - the addition of a hydrophobic side-chain to modulate the ionisation characteristics of the molecule. Thus fosinopril was developed. Fosinopril is administered as a prodrug and is converted in vivo to the active form fosinoprilat.
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