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Captopril information


Captopril
Clinical data
Pronunciation/ˈkæptəprɪl/
Trade namesCapoten, others
AHFS/Drugs.comMonograph
MedlinePlusa682823
Pregnancy
category
  • AU: D
Routes of
administration
By mouth
ATC code
  • C09AA01 (WHO)
Legal status
Legal status
  • US: WARNING[1]
  • EU: Rx-only[2]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability70–75%
MetabolismLiver
Elimination half-life1.9 hours
ExcretionKidney
Identifiers
IUPAC name
  • (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid
CAS Number
  • 62571-86-2 checkY
PubChem CID
  • 44093
IUPHAR/BPS
  • 5158
DrugBank
  • DB01197 checkY
ChemSpider
  • 40130 checkY
UNII
  • 9G64RSX1XD
KEGG
  • D00251 checkY
ChEBI
  • CHEBI:3380 checkY
ChEMBL
  • ChEMBL1560 checkY
PDB ligand
  • X8Z (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID1037197 Edit this at Wikidata
ECHA InfoCard100.057.806 Edit this at Wikidata
Chemical and physical data
FormulaC9H15NO3S
Molar mass217.28 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C(O)[C@H]1N(C(=O)[C@H](C)CS)CCC1
InChI
  • InChI=1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7+/m1/s1 checkY
  • Key:FAKRSMQSSFJEIM-RQJHMYQMSA-N checkY
  (verify)

Captopril, sold under the brand name Capoten among others, is an angiotensin-converting enzyme (ACE) inhibitor used for the treatment of hypertension and some types of congestive heart failure. Captopril was the first oral ACE inhibitor found for the treatment of hypertension.[3] It does not cause fatigue as associated with beta-blockers. Due to the adverse drug event of causing hyperkalemia, as seen with most ACE Inhibitors, the medication is usually paired with a diuretic.

Captopril was patented in 1976 and approved for medical use in 1980.[4]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ "List of nationally authorised medicinal products Active substance: captopril" (PDF). ema.europa.eu. European Medicines Agency. 26 November 2020. Archived from the original (PDF) on 31 October 2021.
  3. ^ Vidt DG, Bravo EL, Fouad FM (January 1982). "Medical intelligence drug therapy: captopril". The New England Journal of Medicine. 306 (4): 214–219. doi:10.1056/nejm198201283060405. PMID 7033784.
  4. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 467. ISBN 978-3-527-60749-5.

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ACE inhibitor

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inhibitors include benazepril, zofenopril, perindopril, trandolapril, captopril, enalapril, lisinopril, and ramipril. ACE inhibitors were initially approved...

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The captopril challenge test (CCT) is a non-invasive medical test that measures the change in renin plasma-levels in response to administration of captopril...

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Captopril suppression test

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The captopril suppression test (CST) is a non-invasive medical test that measures plasma levels of aldosterone. Aldosterone production is suppressed by...

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Lisinopril

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temperature), less soluble in methanol, and virtually insoluble in ethanol. Captopril, the first ACE inhibitor, is a functional and structural analog of a peptide...

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Enalapril

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Enalapril has a slower onset of action than Captopril but a greater duration of action. However, unlike Captopril, Enalapril does not have a thiol moiety...

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Enalaprilat

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developed partly to overcome these limitations of captopril. The thiol functional group of captopril was replaced with a carboxylic acid group, but additional...

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Discovery and development of ACE inhibitors

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pressure. This led to the development of captopril, the first ACE inhibitor. When the adverse effects of captopril became apparent new derivates were designed...

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Miguel Ondetti

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23, 2004) was an Argentine-born American chemist who first synthesized captopril, the first ACE inhibitor that was used to treat heart disease. With his...

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Follicular hyperplasia

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as Atenolol or ACE inhibitors like Captopril, can cause certain lymphadenopathies for some individuals. Captopril is an analog to proline and completely...

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Venoms in medicine

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animals with small amounts of venom, using their blood as the antidote. Captopril emulates the function of the toxin found in Brazilian pit viper (Bothrops...

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Radioisotope renography

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vascularity of the kidney to be transplanted and with a test dose of captopril to highlight possible renal artery stenosis in the donor's other kidney...

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Hydrochlorothiazide

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Zestoretic (with lisinopril), Co-Renitec (with enalapril), Capozide (with captopril), Accuretic (with quinapril), Monopril HCT (with fosinopril), Lotensin...

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Pulse pressure

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hydrochlorothiazide (a thiazide diuretic), atenolol (a beta-blocker), captopril (an ACE inhibitor), clonidine (a central α2-agonist), diltiazem (a calcium...

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Isosorbide mononitrate

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of other exogenous sources of sulfhydryl groups such as methionine and captopril may produce a similar interaction.[medical citation needed] Phenylalkylamine...

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Bradykinin

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orally was developed: the first angiotensin converting enzyme inhibitor captopril. [citation needed] It was approved by the FDA for the treatment of hypertension...

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Prodrug

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Metabolic tissues (liver, GI mucosal cell, lung etc.) Carbamazepine, captopril, carisoprodol, heroin, molsidomine, leflunomide, paliperidone, phenacetin...

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Antihypertensive drug

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conversion of angiotensin I into angiotensin II, a potent vasoconstrictor. captopril enalapril fosinopril lisinopril moexipril perindopril quinapril ramipril...

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Renal artery stenosis

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Auscultation (with stethoscope) - bruit ("rushing" sound) Captopril challenge test Captopril test dose effect on the differential renal function as measured...

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Bullous pemphigoid

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furosemide, nonsteroidal anti-inflammatory agents, DPP-4 inhibitors, captopril, penicillamine, and antibiotics. The bullae are formed by an immune reaction...

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Hypertensive urgency

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few hours. Recommended medications for hypertensive urgencies include: captopril, labetalol, amlodipine, felodipine, isradipine, and prazosin. Sublingual...

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Metamizole

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minutes before metamizole. Oral anticoagulants (blood thinners), lithium, captopril, triamterene and antihypertensives may also interact with metamizole,...

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Orthostatic hypertension

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successfully used for this condition are medications doxazosin, carvedilol, captopril, and propranolol hydrochloride. Treatment of coexisting conditions, e...

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Polypharmacy

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citation needed] Both captopril and lisinopril are examples of ACE inhibitors. However, lisinopril is dosed once a day, whereas captopril may be dosed 2-3...

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CST

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Socialista dos Trabalhadores), in Brazil Canadian Society of Transplantation Captopril suppression test Cavernous sinus thrombosis Cell Signaling Technology...

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Probenecid

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the important clinical interactions of probenecid include those with captopril, indomethacin, ketoprofen, ketorolac, naproxen, cephalosporins, quinolones...

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Serum sickness

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the drugs associated with serum sickness are: allopurinol barbiturates captopril cephalosporins crofab griseofulvin penicillins phenytoin procainamide...

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International nonproprietary name

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-olol for beta blockers (e.g. atenolol) -pril for ACE inhibitors (e.g. captopril) -sartan for angiotensin II receptor antagonists (e.g. losartan) -tinib...

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Alacepril

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indicated as a treatment for hypertension. The medication metabolizes to captopril and desacetylalacepril. Alacepril is primarily used to treat hypertension...

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