Captopril: Difference between revisions

Revision as of 15:42, 26 March 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]

For patient information about Captopril, click here.

Synonyms / Brand Names: Capoten

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(11% ), disorder of taste, cough (0.5% to 2%). hypotension, rash, hyperkalemia (11% ), disorder of taste, cough (0.5% to 2%).

Prescribing Information

Captopril tablet

Captopril

Captopril and Hydrochlorothiazide tablet

Captopril and Hydrochlorothiazide tablet

References

Atkinson AB, Robertson JIS. Captopril in the treatment of hypertension and cardiac failure. Lancet 1979;2(8147):836–9. PMID 90928
Patchett AA, Harris E, Tristam EQ, et al. A new class of angiotensin-converting enzyme inhibitors. Nature 1980;288(5788):280–3. PMID 6253826
Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006.
Smith CG, Vane JR. The discovery of captopril. FASEB J 2003;17:788-9. Fulltext. PMID 12724335.

External links

Template:ACE inhibitors

@@ Line 1: / Line 1: @@
-{{Captopril}}
-{{drugbox |
-| image=Captopril.png
-| width=160px
-| IUPAC_name = (''2S'')-1-<nowiki>[</nowiki>(''2S'')-2-methyl-3-sulfanylpropanoyl<nowiki>]</nowiki><br />pyrrolidine-2-carboxylic acid
-| CAS_number = 62571-86-2
-| ATC_prefix= C09
-| ATC_suffix= AA01
-| PubChem=44093
-| DrugBank=APRD00164
-| C=9 | H=15 | N=1 | O=3 | S=1
-| molecular_weight = 217.29
-| bioavailability = 70–75%
-| metabolism = [[hepatic]]
-| elimination_half-life = 1.9 hours
-| excretion = [[renal]]
-| pregnancy_AU = D
-| pregnancy_US =
-| pregnancy_category =
-| legal_status = Rx-only
-| routes_of_administration = oral
-}}
 __NOTOC__
-{{CMG}}; {{AE}} {{AM}}
+{{CMG}}; {{AE}} {{AM}}, {{AZ}}
 '''''For patient information about Captopril, click [[Captopril (patient information)|here]].'''''
@@ Line 30: / Line 8: @@
 ==Overview==
-'''Captopril''' ([[International Nonproprietary Name|rINN]]) ([[International Phonetic Alphabet|IPA]]: {{IPA|[ˈkæptəprɪl]}}) is an [[angiotensin-converting enzyme]] inhibitor ([[ACE inhibitor]]) used for the treatment of [[hypertension]] and some types of [[congestive heart failure]]. Captopril was the first [[ACE inhibitor]] developed and was considered a breakthrough both because of its novel mechanism of action and also because of the revolutionary development process. Captopril is commonly marketed by [[Bristol-Myers Squibb]] under the trade name '''Capoten'''.
+'''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(11% ), disorder of taste, cough (0.5% to 2%). [[hypotension]], [[rash]], [[hyperkalemia]] (11% ), disorder of taste, [[cough]] (0.5% to 2%).
 ==Category==
@@ Line 36: / Line 14: @@
 Antihypertensive Agents, ACE Inhibitors.
-==FDA Package Insert==
+==Prescribing Information==
-====CAPTOPRIL (captopril ) tablet====
+===''[[Captopril tablet ]]''===
-'''  [[Captopril indications and usage|Indications and Usage]]'''
+* [[Captopril]]
-'''| [[Captopril dosage and administration|Dosage and Administration]]'''
-'''| [[Captopril contraindications|Contraindications]]'''
-'''| [[Captopril warnings and precautions|Warnings and Precautions]]'''
-'''| [[Captopril adverse reactions|Adverse Reactions]]'''
-'''| [[Captopril drug interactions|Drug Interactions]]'''
-'''| [[Captopril use in specific populations|Use in Specific Populations]]'''
-'''| [[Captopril overdosage|Overdosage]]'''
-'''| [[Captopril description|Description]]'''
-'''| [[Captopril clinical pharmacology|Clinical Pharmacology]]'''
-'''| [[Captopril clinical studies|Clinical Studies]]'''
-'''| [[Captopril how supplied storage and handling|How Supplied/Storage and Handling]]'''
-'''| [[Captopril patient counseling information|Patient Counseling Information]]'''
-'''| [[Captopril labels and packages|Labels and Packages]]'''
-{|
+===''[[Captopril and Hydrochlorothiazide tablet]]''===
-| [[File:001.png|800px|thumb]]
-|}
-{{Reflist|2}}
+* [[Captopril and Hydrochlorothiazide tablet]]
-[[Category:Cardiovascular Drugs]]
-[[Category:Drugs]]
-==Clinical Use==
-Captopril's main uses are based on its [[vasodilatation]] and inhibition of renal function.  These benefits are most clearly seen in the following conditions:
-* [[Hypertension]]
-* Cardiac conditions such as post-[[myocardial infarction]] and [[congestive heart failure]]
-* Preservation of kidney function in [[diabetic nephropathy]]
-==History==
-Captopril was developed in 1975 by three researchers at the U.S. drug company Squibb (now [[Bristol-Myers Squibb]]): Miguel Ondetti, Bernard Rubin and David Cushman. Squibb filed for U.S. patent protection on the drug in February 1976 and U.S. Patent 4,046,889 was granted in September 1977.
-The development of captopril was amongst the earliest successes of the revolutionary concept of structure-based drug design. The [[renin-angiotensin system|renin-angiontensin-aldosterone]] system had been extensively studied in the mid-20th century and it had been decided that this system presented several opportune targets in the development of novel treatments for hypertension. The first two targets that were attempted were [[renin]] and [[Angiotensin-Converting Enzyme|ACE]]. Captopril was the culmination of efforts by Squibb's laboratories to develop an ACE inhibitor.
-Ondetti, Cushman and colleagues built on work that had been done in the 1960s by the British pharmacologist [[John Robert Vane|John Vane]] when he was a researcher at the [[Royal College of Surgeons of England]]. Working with a Brazilian colleague, [[Sérgio Henrique Ferreira|Sérgio Ferreira]], Vane discovered a [[peptide]] in pit viper (''[[Bothrops jararaca]]'') venom which was a 'collected-product inhibitor' of angiotensin II. Captopril was developed from this peptide after it was found via [[Quantitative structure-activity relationship|QSAR]]-based modification that the terminal [[sulfhydryl]] moiety of the peptide provided a high potency of ACE inhibition.
-Captopril gained FDA approval in June 1981. The drug went generic in the U.S. in February 1996 as a result of the end of market exclusivity for Bristol-Myers Squibb.
-==Chemical synthesis==
-A chemical synthesis of captopril by treatment of L-proline with (2S)-3-acetylthio-2-methylpropanoyl chloride under basic conditions (NaOH), followed by aminolysis of the protective acetyl group to unmask the drug's free thiol, is depicted in the figure at right.
-==Developments from captopril==
-===Limitations of captopril===
-The [[adverse drug reaction]] (ADR) profile of captopril is similar to other [[ACE inhibitor]]s, with cough being the most common ADR (Rossi, 2006). However, captopril is also commonly associated with rash and taste disturbances (metallic or loss of taste), which are attributed to the unique [[sulfhydryl]] moiety (Atkinson & Robertson, 1979).
-Captopril also has a relatively poor pharmacokinetic profile. The short [[elimination half-life|half-life]] necessitates 2–3 times daily dosing, which may reduce patient [[Compliance (medicine)|compliance]].
-===Subsequent ACE inhibitors===
-The adverse effect and pharmacokinetic limitations of captopril stimulated the development [[enalapril]] and subsequent [[ACE inhibitor]]s. These were specifically designed to lack the sulfhydryl moiety believed to be responsible for [[rash]] and [[taste disturbance]] (Patchett et al., 1980). Most subsequent ACE inhibitors are given as [[prodrug]]s, to improve oral [[bioavailability]]. All have a longer half-life and are given once daily, which may improve patient compliance.
 ==References==