Fosinopril: Difference between revisions

Jump to navigation Jump to search
← Older editNewer edit →
VisualWikitext
Gerald Chi- (talk | contribs)
Bureaucrats, bureaucrats, nocaptcha, oversight, smwadministrator, Administrators, Widget editors
7,699 edits
m Changed protection level for "Fosinopril" ([Edit=Allow only autoconfirmed users] (expires 15:32, 27 February 2014 (UTC)) [Move=Allow only autoconfirmed users] (expires 15:32, 27 February 2014 (UTC)))
Gerald Chi- (talk | contribs)
Bureaucrats, bureaucrats, nocaptcha, oversight, smwadministrator, Administrators, Widget editors
7,699 edits
No edit summary
Line 1: Line 1:
<small>'''''Synonyms / Brand Names:''''' </small>
{{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
}}
__NOTOC__
{{CMG}}
 


{{CMG}}


==Dosing and Administration==
==[[Fosinopril (patient information)|For patient information, click here]]==
<br>
----
<br>
<font size="4">
[[{{PAGENAME}}#FDA Package Insert Resources|FDA Package Insert Resources]]
<br></font size><small>Indications, Contraindications, Side Effects, Drug Interactions, etc.</small><font size="4"><br>
<br>
[http://www.pace-med-apps.com/gfrcalc.htm Calculate Creatine Clearance]
<br></font size><small>On line calculator of your patients Cr Cl by a variety of formulas.</small><font size="4"><br>
<br>
[http://home.earthlink.net/~sensei11/convert.htm Convert pounds to Kilograms]
<br></font size><small>On line calculator of your patients weight in pounds to Kg for dosing estimates.</small><font size="4"><br>
<br> [[{{PAGENAME}}#Publication Resources|Publication Resources]]
<br></font size><small>Recent articles, WikiDoc State of the Art Review, Textbook Information</small><font size="4"><br>
<br>
[[{{PAGENAME}}#Trial Resources|Trial Resources]]
<br></font size><small>Ongoing Trials, Trial Results</small><font size="4"><br>
<br>
[[{{PAGENAME}}#Guidelines & Evidence Based Medicine Resources|Guidelines & Evidence Based Medicine Resources]]
<br></font size><small>US National Guidelines, Cochrane Collaboration, etc.</small><font size="4"><br>
<br>
[[{{PAGENAME}}#Media Resources|Media Resources]]
<br></font size><small>Slides, Video, Images, MP3, Podcasts, etc.</small><font size="4"><br><br>
[[{{PAGENAME}}#Patient Resources|Patient Resources]]
<br></font size><small>Discussion Groups, Handouts, Blogs, News, etc.</small><font size="4"><br>
<br>
[[{{PAGENAME}}#International Resources|International Resources]]
<br></font size><small>en Español</small><font size="4"><br>
<br>
----
<br>
<br>
<br>
<br>


==FDA Package Insert Resources==
'''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®'''.
[[{{PAGENAME}} indications|Indications]]
<br>
<br>
[[{{PAGENAME}} contraindications|Contraindications]]
<br>
<br>
[[{{PAGENAME}} side effects|Side Effects]]
<br>
<br>
[[{{PAGENAME}} drug interactions|Drug Interactions]]
<br>
<br>
[[{{PAGENAME}} precautions|Precautions]]
<br>
<br>
[[{{PAGENAME}} overdose|Overdose]]
<br>
<br>
[[{{PAGENAME}} instructions for administration|Instructions for Administration]]
<br>
<br>
[[{{PAGENAME}} how supplied|How Supplied]]
<br>
<br>
[[{{PAGENAME}} pharmacokinetics and molecular data|Pharmacokinetics and Molecular Data]]
<br>
<br>
[http://www.fda.gov/ohrms/dockets/dockets/06p0209/06P-0209-EC12-Attach-1.pdf FDA label]
<br>
<br>
[http://google2.fda.gov/search?q={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}&x=0&y=0&client=FDA&site=FDA&lr=&proxystylesheet=FDA&output=xml_no_dtd&getfields=* FDA on {{PAGENAME}}]
<br>
<br>
</font size><small>[[{{PAGENAME}}#Dosing and Administration|Return to top]]</small><font size="4">
<br>
<br>


==Publication Resources==
==Development==
[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?CMD=search&db=pubmed&term={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}} Most Recent Articles on {{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}]
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.
<br>
<br>
[http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=search&db=pubmed&term={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}%20AND%20systematic%5Bsb%5D  Review Articles on {{PAGENAME}}]
<br>
<br>
[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=search&db=pubmed&term={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}+AND+%28%28N+Engl+J+Med%5Bta%5D%29+OR+%28Lancet%5Bta%5D%29+OR+%28BMJ%5Bta%5D%29%29 Articles on {{PAGENAME}} in N Eng J Med, Lancet, BMJ]
<br>
<br>
[[WikiDoc state of the art review on {{PAGENAME}}|WikiDoc State of the Art Review]]
<br>
<br>
[http://books.google.com/books?ie=UTF-8&oe=utf-8&q={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}&qt_s=Search&sa=N&tab=gp Textbook Information on {{PAGENAME}}]
<br>
<br>
</font size><small>[[{{PAGENAME}}#Dosing and Administration|Return to top]]</small><font size="4">
<br>
<br>


==Trial Resources==
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.
[http://clinicaltrials.gov/search/open/condition={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}} Ongoing Trials with {{PAGENAME}} at Clinical Trials.gov]
<br>
<br>
[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=search&db=pubmed&term={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}+AND+%28randomized+controlled+trial%5BPublication+Type%5D+OR+%28randomized%5BTitle%2FAbstract%5D+AND+controlled%5BTitle%2FAbstract%5D+AND+trial%5BTitle%2FAbstract%5D%29%29 Trial Results with {{PAGENAME}}]
<br>
<br>
</font size><small>[[{{PAGENAME}}#Dosing and Administration|Return to top]]</small><font size="4">
<br>
<br>


==Guidelines & Evidence Based Medicine Resources==
==Fosinoprilat and Fosinopril==
[http://www.guideline.gov/search/searchresults.aspx?Type=3&txtSearch={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}&num=20 US National Guidelines Clearinghouse on {{PAGENAME}}]
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.
<br>
<br>
[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=search&db=pubmed&term={{urlencode:({{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}) AND (Cochrane Database Syst Rev[ta])}} Cochrane Collaboration on {{PAGENAME}}]
<br>
<br>
[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=search&db=pubmed&term={{urlencode:({{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}) AND (Cost effectiveness)}} Cost Effectiveness of {{PAGENAME}}]
<br>
<br>
</font size><small>[[{{PAGENAME}}#Dosing and Administration|Return to top]]</small><font size="4">
<br>
<br>
==Media Resources==
[http://www.google.com/search?q={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}+ppt&ie=utf-8&oe=utf-8&aq=t&rls=org.mozilla:en-US:official&client=firefox-a Powerpoint Slides on {{PAGENAME}}]
<br>
<br>
[http://images.google.com/images?q={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}&ie=UTF-8&oe=utf-8&rls=org.mozilla:en-US:official&client=firefox-a&um=1&sa=N&tab=wi Images of {{PAGENAME}}]
<br>
<br>
[http://www.google.com/search?hl=en&client=firefox-a&rls=org.mozilla%3Aen-US%3Aofficial&hs=hPo&q={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}+podcasts+OR+MP3&btnG=Search Podcasts & MP3s on {{PAGENAME}}]
<br>
<br>
[http://video.google.com/videosearch?q={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}&ie=UTF-8&oe=utf-8&rls=org.mozilla:en-US:official&um=1&sa=N&tab=fv# Videos on {{PAGENAME}}]
<br>
<br>
</font size><small>[[{{PAGENAME}}#Dosing and Administration|Return to top]]</small><font size="4">
<br>
<br>


==Patient Resources==
[[{{PAGENAME}} (patient information)|Patient Information from National Library of Medicine]]
<br>
<br>
[http://www.google.com/search?hl=en&q={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}+more:for_patients&cx=disease_for_patients&sa=N&oi=cooptsr&resnum=0&ct=col3&cd=1  Patient Resources on {{PAGENAME}}]
<br>
<br>
[http://groups.google.com/groups/search?ie=UTF-8&oe=utf-8&q={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}&qt_s=Search Discussion Groups on {{PAGENAME}}]
<br>
<br>
[http://www.google.com/search?hl=en&client=firefox-a&rls=org.mozilla:en-US:official&q={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}+more:patient_handouts&cx=disease_for_health_professionals&sa=N&oi=coopctx&resnum=0&ct=col1&cd=3 Patient Handouts on {{PAGENAME}}]
<br>
<br>
[http://blogsearch.google.com/blogsearch?q={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}&ie=UTF-8&oe=utf-8&rls=org.mozilla:en-US:official&client=firefox-a&um=1&sa=N&tab=wb Blogs on {{PAGENAME}}]
<br>
<br>
[http://news.google.com/news?q={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}&ie=UTF-8&oe=utf-8&rls=org.mozilla:en-US:official&client=firefox-a&um=1&sa=N&tab=wn {{PAGENAME}} in the News]
<br>
<br>
[http://finance.google.com/finance?ie=UTF-8&oe=utf-8&q={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}&qt_s=Search&sa=N&tab=te {{PAGENAME}} in the Marketplace]
<br>
<br>
</font size><small>[[{{PAGENAME}}#Dosing and Administration|Return to top]]</small><font size="4">
<br>
<br>


==International Resources==
{{ACE inhibitors}}
[http://www.google.com/search?q={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}+en+espanol&ie=utf-8&oe=utf-8&aq=t&rls=org.mozilla:en-US:official&client=firefox-a {{PAGENAME}} en Español]
<br>
<br>
</font size><small>[[{{PAGENAME}}#Dosing and Administration|Return to top]]</small><font size="4">
<br>
<br>
</font size>
----
{{FDA}}


[[Category:ACE inhibitors]]
[[Category:Drugs]]
[[Category:Drugs]]
[[de:Fosinopril]]
[[hr:Fosinopril]]
[[hu:Fosinopril]]
{{WikiDoc Help Menu}}
{{WikiDoc Sources}}

Revision as of 15:33, 13 February 2014

Fosinopril
Clinical data
Pregnancy
category
  • AU: D
Routes of
administration		oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability~36%
Protein binding87% (fosinoprilat)
Metabolismhepatic, GIT mucosa (to fosinoprilat)
Elimination half-life12 hours (fosinoprilat)
Excretionrenal
Identifiers
CAS Number
PubChem CID
DrugBank
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC30H46NO7P
Molar mass563.663 g/mol

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]


For patient information, click here

Fosinopril is an 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®.

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 Zn2+ 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.


Template:ACE inhibitors

de:Fosinopril hr:Fosinopril hu:Fosinopril


Template:WikiDoc Sources

Retrieved from "https://www.wikidoc.org/index.php?title=Fosinopril&oldid=943114"