captopril

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A drug used in the treatment of cardiovascular diseases, such as hypertension and congestive heart failure, that functions by inhibiting the enzymes that activate angiotensin.

[(MER)CAPT(AN) + PR(OPANE) + alteration of –YL.]

trade name: Capoten; drug class: angiotensin-converting enzyme; action: dilation of arterial and venous vessels; uses: hypertension.

Brand names: Capoten®

Chemical formula:

Drug Forms:
• Captopril Oral tablet (below)
• Captopril tablets

Español:
• Captopril, Tableta oral
• Tabletas de captopril

Captopril Oral tablet

What is this medicine?

CAPTOPRIL is an ACE inhibitor. This medicine is used to treat high blood pressure and heart failure. It is used to treat heart damage after a heart attack. It can also slow the progression of kidney disease in diabetic patients.

This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
•bone marrow disease
•heart or blood vessel disease
•if you are on a special diet, such as a low salt diet
•immune system disease like lupus or scleroderma
•kidney disease
•low blood pressure
•previous swelling of the tongue, face, or lips with difficulty breathing, difficulty swallowing, hoarseness, or tightening of the throat
•an unusual or allergic reaction to captopril, other ACE inhibitors, insect venom, foods, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding

How should I use this medicine?

Take this medicine by mouth with a glass of water. Follow the directions on your prescription label. Take this medicine on an empty stomach, at least 1 hour before meals. Take your doses at regular intervals. Do not take more medicine than directed. Do not stop taking this medicine except on the advice of your doctor or health care professional.

Talk to your pediatrician regarding the use of this medicine in children. Special care may be needed.

Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.

What may interact with this medicine?

•antacids
•diuretics
•lithium
•medicines for chest pain like nitroglycerin
•medicines for high blood pressure
•NSAIDs, medicines for pain and inflammation, like ibuprofen or naproxen
•over-the-counter herbal supplements like hawthorn
•potassium salts or potassium supplements

This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.

What should I watch for while using this medicine?

Visit your doctor or health care professional for regular checks on your progress. Check your blood pressure as directed. Ask your doctor or health care professional what your blood pressure should be and when you should contact him or her. Call your doctor or health care professional if you notice an irregular or fast heart beat.

Women should inform their doctor if they wish to become pregnant or think they might be pregnant. There is a potential for serious side effects to an unborn child. Talk to your health care professional or pharmacist for more information.

Check with your doctor or health care professional if you get an attack of severe diarrhea, nausea and vomiting, or if you sweat a lot. The loss of too much body fluid can make it dangerous for you to take this medicine.

You may get drowsy or dizzy. Do not drive, use machinery, or do anything that needs mental alertness until you know how this drug affects you. Do not stand or sit up quickly, especially if you are an older patient. This reduces the risk of dizzy or fainting spells. Alcohol can make you more drowsy and dizzy. Avoid alcoholic drinks.

Avoid salt substitutes unless you are told otherwise by your doctor or health care professional.

Do not treat yourself for coughs, colds, or pain while you are taking this medicine without asking your doctor or health care professional for advice. Some ingredients may increase your blood pressure.

What side effects may I notice from receiving this medicine?

Side effects that you should report to your doctor or health care professional as soon as possible:
•allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
•breathing problems
•chest pain
•dark urine
•feeling faint or lightheaded, falls
•fever or sore throat
•irregular heart beat
•pain or difficulty passing urine
•redness, blistering, peeling or loosening of the skin, including inside the mouth
•stomach pain with or without nausea or vomiting
•unusually weak
•yellowing of the eyes or skin

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•change in sex drive or performance
•cough
•loss of taste
•sun sensitivity
•tiredness

This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

Where should I keep my medicine?

Keep out of the reach of children.

Store at room temperature below 30 degrees C (86 degrees F). Protect from moisture. Keep container tightly closed. Throw away any unused medicine after the expiration date.

Last updated: 7/1/2002

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

An angiotensin-converting enzyme (ACE) inhibitor used as a vasodilator in the treatment of congestive heart failure, mitral regurgitation and hypertension. Now often replaced by newer ACE inhibitors such as enalapril, lisinopril.

Captopril
Systematic (IUPAC) name
(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl] pyrrolidine-2-carboxylic acid
Identifiers
CAS number	62571-86-2
ATC code	C09AA01
PubChem	44093
DrugBank	APRD00164
ChemSpider	40130
Chemical data
Formula	C9H15NO3S
Mol. mass	217.29
Pharmacokinetic data
Bioavailability	70–75%
Metabolism	hepatic
Half life	1.9 hours
Excretion	renal
Therapeutic considerations
Pregnancy cat.	D(AU)
Legal status	℞ Prescription only
Routes	oral

Captopril (rINN) (pronounced /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.

Contents 1 Clinical use 2 History 3 Developments from captopril 3.1 Limitations of captopril 3.2 Subsequent ACE inhibitors 4 Adverse effects 5 References 6 See also 7 External links

Clinical use

Captopril's main uses are based on its vasodilatation and inhibition of some renal function activities. These benefits are most clearly seen in the following conditions:

1) Hypertension

2) Cardiac conditions such as post myocardial infarction and congestive heart failure

3) Preservation of kidney function in diabetic nephropathy

Additionally, it has shown mood-elevating properties in some patients. This is consistent with the observation that animal screening models indicate putative antidepressant activity for this compound, although there has been one negative study. Formal clinical trials in depressed patients have not been reported.^[1]

It has also been investigated for use in the treatment of cancer.^[2]

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-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 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 a team of researchers led by John Vane at the Royal College of Surgeons of England. The first breakthrough was made by Kevin K.F.Ng ^[3][4][5] in 1967 when he found that the conversion of angiotensin I to angiotensin II took place in the pulmonary circulation instead of in the plasma. In contrast, Sergio Ferreira^[6][7] found that bradykinin disappeared in its passage through the pulmonary circulation. The conversion of angiotensin I to angiotensin II and the inactivation of bradykinin was thought to be mediated by the same enzyme.

In 1970, using bradykinin potentiating factor (BPF) provided by Sergio Ferreira,^[8] Ng and Vane found that the conversion of angiotensin I to angiotensin II was inhibited during its passage through the pulmonary circulation. BPF was later found to be a peptide in the pit viper (Bothrops jararaca) venom which was a “collected-product inhibitor” of the converting enzyme. Captopril was developed from this peptide after it was found via 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.

Developments from captopril

Limitations of captopril

The adverse drug reaction (ADR) profile of captopril is similar to other ACE inhibitors, with cough being the most common ADR.^[9] However, captopril is also commonly associated with rash and taste disturbances (metallic or loss of taste), which are attributed to the unique sulfhydryl moiety.^[10]

Captopril also has a relatively poor pharmacokinetic profile. The short half-life necessitates 2–3 times daily dosing, which may reduce patient compliance.

Subsequent ACE inhibitors

The adverse effect and pharmacokinetic limitations of captopril stimulated the development enalapril and subsequent ACE inhibitors. These were specifically designed to lack the sulfhydryl moiety believed to be responsible for rash and taste disturbance.^[11] Most subsequent ACE inhibitors are given as prodrugs, to improve oral bioavailability. All have a longer half-life and are given once or twice daily, which may improve patient compliance.

Adverse effects

Main article: ACE inhibitor#Adverse effects

Adverse effects of captopril include cough, angioedema, agranulocystosis, proteinuria, hyperkalemia, taste alteration, teratogenicity, postural hypotension, acute renal failure and leukopenia. ^[12]. Except for postural hypotension which occurs due to short and fast mode of action of captopril, most of the side effects mentioned are common for all ACE inhibitors. Among these cough is the most common adverse effect and is due to elevated levels of bradykinin. Hyperkalemia can occur especially if used along with other drugs which elevate potassium level in blood like potassium sparing diuretics.

References

1. ^ Novel Pharmacological Approaches to the Treatment of Depression
2. ^ Attoub S, Gaben AM, Al-Salam S, et al. (September 2008). "Captopril as a potential inhibitor of lung tumor growth and metastasis". Ann. N. Y. Acad. Sci. 1138: 65–72. doi:10.1196/annals.1414.011. PMID 18837885. http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0077-8923&date=2008&volume=1138&spage=65. 
3. ^ Ng KKF and Vane JR: Conversion of angiotensin I to angiotensin II. Nature 1967, 216, 762-766.
4. ^ Ng KKF and Vane JR: Fate of angiotensin I in the circulation. Nature, 1968, 218, 144-150.
5. ^ Ng KKF and Vane JR: Some properties of angiotensin converting enzyme in the lung in vivo. Nature, 1970, 225, 1142-1144.
6. ^ * Ferreira SH and Vane JR: The disappearance of bradykinin and eledoisin in the circulation and vascular beds of the cat. Br. J. Pharm. Chemother.,1967,30, 417-424.
7. ^ Ferreira SH and Vane JR: The disappearance of bradykinin and eledoisin in the circulation and vascular beds of the cat. Br. J. Pharm. Chemother.,1967,30, 417-424.
8. ^ Smith CG, Vane JR (May 2003). "The discovery of captopril". FASEB J. 17 (8): 788–9. doi:10.1096/fj.03-0093life. PMID 12724335. http://www.fasebj.org/cgi/pmidlookup?view=long&pmid=12724335. 
9. ^ Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006.
10. ^ Atkinson AB, Robertson JIS. Captopril in the treatment of hypertension and cardiac failure. Lancet 1979;2(8147):836–9. PMID 90928
11. ^ Patchett AA, Harris E, Tristam EQ, et al. A new class of angiotensin-converting enzyme inhibitors. Nature 1980;288(5788):280–3. PMID 6253826
12. ^ "Captopril (ACE inhibitor): side effects". lifehugger. 07-09-2008. http://mc.lifehugger.com/moc/157/captopril-ace-inhibitor-side-effects. Retrieved on 2009-05-02. 

See also

• Captopril challenge test
• Captopril suppression test

External links

• Captopril side effects: Mnemonic
• U.S. Patent 4,046,889
• RxList monograph: Capoten

v • d • e Antihypertensives: agents acting on the renin-angiotensin system (C09) ACE inhibitors ("-pril") Sulfhydryl-containing: Captopril • Zofenopril Dicarboxylate-containing: Enalapril# • Ramipril • Quinapril • Perindopril • Lisinopril • Benazepril Phosphonate-containing: Fosinopril Other/ungrouped: Alacepril • Cilazapril • Delapril • Imidapril • Moexipril • Rentiapril • Spirapril • Temocapril • Trandolapril AIIRAs/ ("-sartan") Azilsartan • Candesartan • Eprosartan • Irbesartan • Losartan • Olmesartan • Tasosartan • Telmisartan • Valsartan Renin inhibitors/ ("-kiren") Aliskiren • Remikiren #WHO-EM. †Undergoing clinical trials, not FDA approved. ‡Withdrawn from market. §Development halted.

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