Fosinopril: Difference between revisions

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__NOTOC__
__NOTOC__
{{Fosinopril}}
{{Fosinopril}}
{{drugbox
| IUPAC_name = 4-cyclohexyl-1-[2-[(2-methyl-1-propanoyloxy-propoxy)- (4-phenylbutyl)phosphoryl]acetyl] -pyrrolidine-2-carboxylic acid<br>(Diagrams above are fosinopril and fosinoprilat, respectively. Data below refers to fosinopril unless indicated)
| image = fosinopril.png
| image2 = fosinoprilat.png
| CAS_number = 98048-97-6
| ATC_prefix = C09
| ATC_suffix = AA09
| ATC_supplemental =
| PubChem = 55891
| DrugBank = APRD00526
| C=30 | H=46 | N=1 | O=7 | P=1
| molecular_weight = 563.663 g/mol
| bioavailability = ~36%
| protein_bound = 87% (fosinoprilat)
| metabolism = [[hepatic]], GIT mucosa (to fosinoprilat)
| elimination_half-life = 12 hours (fosinoprilat)
| excretion=[[renal]]
| pregnancy_AU = D
| pregnancy_US =
| pregnancy_category =
| legal_status = Rx-only
| routes_of_administration = oral
}}
{{CMG}}; {{AE}} {{AM}}
{{CMG}}; {{AE}} {{AM}}


'''''For patient information about Fosinopril, click [[Fosinopril (patient information)|here]].'''''
'''''For patient information about Fosinopril, click [[Fosinopril (patient information)|here]].'''''


{{SB}} MONOPRIL<sup>®</sup>
{{SB}} VASOTEC in the USA, ENALADEX in some other countries, and ENACARD for veterinary use.


==Overview==
==Overview==
 
Fosinopril is an [[angiotensin converting enzyme]] (ACE) inhibitor used in the treatment of [[hypertension]], [[diabetic nephropathy]], and some types of chronic heart failure. [[ACE]] onverts the peptide hormone [[angiotensin I]] to [[angiotensin II]]. One of the actions of angiotensin II is the [[vasoconstriction]] of blood vessels resulting in an increase in [[blood pressure]]. ACE inhibitors such as Fosinopril prevent this effect. Fosinopril has been shown to lower the death rate in systolic [[heart failure]]. Fosinopril was the first member of the group known as the dicarboxylate-containing ACE inhibitors.
'''Fosinopril''' is an [[ACE inhibitor|angiotensin converting enzyme (ACE) inhibitor]] used for the treatment of [[hypertension]] and some types of chronic [[heart failure]]. Fosinopril is the first and only phosphonate-containing ACE inhibitor marketed. It is marketed by [[Bristol-Myers Squibb]] under the trade name '''Monopril®'''.


==Category==
==Category==
Antihypertensive Agents, ACE Inhibitors.
Antihypertensive Agents, ACE Inhibitors.  
 
==Development==
The development of fosinopril started from the observation of the hypotensive effects of phosphoramidon, an extract from the bacterium [[''Streptomyces tanashiensis'']]. Phosphoramidon was found to be a potent inhibitor of ACE. It was speculated that the phosphoramide moiety in the molecule was central to its inhibition of ACE. Further studies found that the phosphoramide moiety served the dual-purpose of interacting with the Zn<sup>2+</sup> in ACE, as well as mimicking the transition-state of the natural substrate of ACE.
 
These discoveries led to the attempt to develop a new group of ACE inhibitors which contained the phosphoramide moiety. The initial lead proved to be very potent but unstable at physiological [[pH]]. Later compounds would have a phosphonate moiety (being more stable) in place of the phosphoramide. The lessons learnt in the development of [[enalapril]] and later ACE inhibitors were applied to the design  and eventually '''fosinoprilat''' was developed.
 
==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.


==FDA Package Insert==
==FDA Package Insert==
Line 62: Line 29:
'''| [[Fosinopril patient counseling information|Patient Counseling Information]]'''
'''| [[Fosinopril patient counseling information|Patient Counseling Information]]'''
'''| [[Fosinopril labels and packages|Labels and Packages]]'''
'''| [[Fosinopril labels and packages|Labels and Packages]]'''
{|
| [[File:aa9.png|800px|thumb]]
|}
==References==
{{Reflist|2}}
[[Category:Cardiovascular Drugs]]
[[Category:Drugs]]


==Interactions With Alcohol==


{{ACE inhibitors}}
{{FDA}}


[[Category:ACE inhibitors]]
[[Category:Cardiovascular Drugs]]
[[Category:Cardiovascular Drugs]]
[[Category:Drugs]]
[[Category:Drugs]]

Revision as of 12:10, 7 April 2014


Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Amr Marawan, M.D. [2], Ahmed Zaghw, M.D. [3]

Fosinopril

Fosinopril and Hydrochlorothiazide

Overview

Captopril tablet is an angiontensin converting enzyme inhibitor drug that is FDA approved for the treatment of hypertension, heart failure, left ventricular dysfunction after myocardial infarction, diabetic nephropathy. Adverse reactions include hypotension, rash, hyperkalemia, disorder of taste, cough. hypotension, rash, hyperkalemia, disorder of taste, cough.

Category

Antihypertensive Agents, Angiotensin Converting Enzyme Inhibitors. Editor-In-Chief: C. Michael Gibson, M.S., M.D. [4]; Associate Editor(s)-in-Chief: Amr Marawan, M.D. [5]

For patient information about Fosinopril, click here.

Synonyms / Brand Names: VASOTEC in the USA, ENALADEX in some other countries, and ENACARD for veterinary use.

Overview

Fosinopril is an angiotensin converting enzyme (ACE) inhibitor used in the treatment of hypertension, diabetic nephropathy, and some types of chronic heart failure. ACE onverts the peptide hormone angiotensin I to angiotensin II. One of the actions of angiotensin II is the vasoconstriction of blood vessels resulting in an increase in blood pressure. ACE inhibitors such as Fosinopril prevent this effect. Fosinopril has been shown to lower the death rate in systolic heart failure. Fosinopril was the first member of the group known as the dicarboxylate-containing ACE inhibitors.

Category

Antihypertensive Agents, ACE Inhibitors.

FDA Package Insert

Indications and Usage | Dosage and Administration | Contraindications | Warnings and Precautions | Adverse Reactions | Drug Interactions | Use in Specific Populations | Overdosage | Description | Clinical Pharmacology | Clinical Studies | How Supplied/Storage and Handling | Patient Counseling Information | Labels and Packages

Interactions With Alcohol

Adapted from the FDA Package Insert.

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