A drug, C10H16N6S, that inhibits acid secretion in the stomach and is used to treat gastrointestinal disorders, such as peptic ulcers.
[Alteration of CY(ANO–) + MET(HYL) + (GUAN)IDINE.]
cimetidine
Dictionary:
ci·met·i·dine (sĭ-mĕt'ĭ-dēn', -dīn')  |
| 5min Related Video: cimetidine |
| Dental Dictionary: cimetidine |
n
trade names: Tagamet, Apo-Cimetidine; drug class: H2-histamine receptor antagonist; action: inhibits histamine at H2-histamine receptor site in parietal cells, which inhibits gastric acid secretion; uses: short-term treatment of duodenal and gastric ulcers by the control of hyperacidity.
| Drug Info: Cimetidine |
Brand names: Tagamet®Tagamet® HB
Chemical formula:
- Drug Forms:
- Cimetidine oral liquid (below)
- Cimetidine Oral tablet
- Cimetidine Hydrochloride Oral solution
- Cimetidine Hydrochloride Solution for injection
- Cimetidine Hydrochloride, Sodium Chloride Solution for injection
- Español:
- Cimetidina líquida para administración oral
- Cimetidina, Tableta oral
- Cimetidina Clorhidrato, Solución oral
- Clorhidrato de cimetidina, Solución para inyección
- Clorhidrato de cimetidina; Cloruro de sodio, Solución para inyección
Cimetidine oral liquid
What is cimetidine oral liquid?
CIMETIDINE (Tagamet®) is a type of antihistamine that blocks the release of stomach acid. Cimetidine is used to treat gastric and duodenal ulcers. It can relieve ulcer pain and discomfort, and the heartburn from gastroesophageal reflux disease. Generic cimetidine oral liquid is available.
What should I tell my health care provider before I take this medicine?
They need to know if you have any of these conditions:
• blood in your stools (black or tarry stools) or if you have blood in your vomit
• frequently drink alcoholic beverages or smoke
• kidney disease
• liver disease
• other chronic illness
• pain or trouble trying to swallow food
• an unusual or allergic reaction to cimetidine, other medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding
How should I take this medicine?
Take cimetidine oral liquid by mouth. Follow the directions on the prescription label. Shake well before using. Use a specially marked spoon or container to measure your medicine. Ask your pharmacist if you do not have one; household spoons are not always accurate. If you only take cimetidine once a day take it at bedtime. Take your doses at regular intervals. Do not take your medicine more often than directed.
Contact your pediatrician or health care professional regarding the use of this medicine in children. Special care may be needed.
What drug(s) may interact with cimetidine?
Do not take cimetidine if you take the following drugs:
• astemizole
• cisapride
• dofetilide
• pimozide
• terfenadine
Other drugs that can interact with cimetidine include:
• antacids
• beta blockers, often used for high blood pressure or heart problems
• caffeine
• carbamazepine
• carmustine
• cefditoren
• cefpodoxime
• cefuroxime
• clonazepam
• delavirdine
• doxercalciferol
• fentanyl
• female hormones, including contraceptive or birth control pills
• flecainide
• guarana
• ketoconazole
• meperidine
• metformin
• metronidazole
• nifedipine
• medicines for anxiety or sleeping problems, such as diazepam or temazepam
• medicines for heart rhythm problems
• medicines for mental depression
• phenytoin
• theophylline
• triazolam
• warfarin
Tell your prescriber or health care professional about all other medicines you are taking, including non-prescription medicines, nutritional supplements, or herbal products. Also tell your prescriber or health care professional if you are a frequent user of drinks with caffeine or alcohol, if you smoke, or if you use illegal drugs. These may affect the way your medicine works. Check with your health care professional before stopping or starting any of your medicines.
What should I watch for while taking cimetidine?
Tell your prescriber or health care professional if your ulcer pain does not improve or gets worse. You may need to take this medicine for several days as prescribed before your symptoms improve. Finish the full course of liquid prescribed by your prescriber or health care professional even if you feel better.
Do not self-medicate with aspirin, ibuprofen or other antiinflammatory medicines; these can aggravate your ulcer and may make it bleed.
Do not smoke cigarettes or drink alcohol; these increase irritation in your stomach and can lengthen the time it will take for your ulcer to heal.
If you get black, tarry stools or vomit up what looks like coffee grounds, call your prescriber or health care professional at once. You may have a bleeding ulcer.
If you need to take an antacid you should take it at least 1 hour before or 1 hour after cimetidine. Cimetidine will not be as effective if taken at the same time as an antacid.
Do not take other acid-reducing ulcer medications, including those you can buy without a prescription over-the-counter, unless specifically directed to do so by your health care provider.
What side effects may I notice from taking cimetidine?
Side effects with cimetidine are infrequent but include:
• agitation, nervousness, depression, hallucinations
• breast swelling and tenderness, or sexual difficulties (impotence) in men
• dark yellow or brown urine
• diarrhea
• dizziness
• headache
• nausea, vomiting
• redness, blistering, peeling or loosening of the skin, including inside the mouth
• skin rash, itching
• sore throat, fever
• stomach pain
• unusual weakness or tiredness
• unusual bleeding or bruising
• yellowing of the skin or eyes
Let your prescriber or health care professional know if you get any of these side effects.
Where can I keep my medicine?
Keep out of the reach of children in a container that small children cannot open.
Store at room temperature between 15 and 30 degrees C (59 and 86 degrees F). Protect from light. 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.
| Veterinary Dictionary: cimetidine |
A histamine H2-receptor antagonist that inhibits the action of histamine at cell surface receptors of the gastric parietal cells and reduces basal gastric acid secretion and secretion stimulated by food, histamine, gastrin and insulin. It is used for short-term treatment of peptic ulcer and for treatment of pathological hypersecretory conditions.
| Wikipedia: Cimetidine |
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Cimetidine
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| Systematic (IUPAC) name | |
| 2-cyano-1-methyl-3-(2-[(5-methyl-1H-imidazol-4-yl)methylthio]ethyl)guanidine | |
| Identifiers | |
| CAS number | |
| ATC code | A02 |
| PubChem | |
| DrugBank | |
| ChemSpider | |
| Chemical data | |
| Formula | C10H16N6S |
| Mol. mass | 252.34 g/mol |
| Pharmacokinetic data | |
| Bioavailability | 60–70% |
| Protein binding | 15–20% |
| Metabolism | Hepatic |
| Half life | 2 hours |
| Excretion | Renal |
| Therapeutic considerations | |
| Licence data | |
| Pregnancy cat. | |
| Legal status |
Prescription Only (S4)(AU) POM(UK) OTC/℞-only (U.S., dose-dependent) |
| Routes | Oral, parenteral |
Cimetidine (INN) (pronounced /sɨˈmɛtɨdiːn/, /saɪˈmɛtɨdiːn/) is a histamine H2-receptor antagonist that inhibits the production of acid in the stomach. It is largely used in the treatment of heartburn and peptic ulcers. It is marketed by GlaxoSmithKline under the trade name Tagamet (sometimes Tagamet HB or Tagamet HB200) and was approved by the Food & Drug Administration for prescriptions starting January 1, 1979.
Contents |
Clinical use
History and development
Cimetidine was the prototypical histamine H2-receptor antagonist from which the later members of the class were developed. Cimetidine was the culmination of a project at Smith, Kline & French (SK&F; now GlaxoSmithKline) by James W. Black, C. Robin Ganellin, and others to develop a histamine receptor antagonist to suppress stomach acid secretion. This was one of the first drugs discovered using a rational drug design approach, thanks to the valiant efforts of medicinal chemists C. Robin Ganellin and Graham Durant and pharmacologist James Black at Smith, Kline, & French Laboratories (now GlaxoSmithKline; Sir James W. Black shared the 1988 Nobel Prize in Physiology or Medicine for the discovery of propranolol and also is credited for the discovery of this drug; actually, the medicinal chemists would have made the discovery).[1]
At the time (1964) it was known that histamine was able to stimulate the secretion of stomach acid, but also that traditional antihistamines had no effect on acid production. In the process, the SK&F scientists also proved the existence of histamine H2-receptors.
The SK&F team used a rational drug-design structure starting from the structure of histamine - the only design lead, since nothing was known of the then hypothetical H2-receptor. Hundreds of modified compounds were synthesised in an effort to develop a model of the receptor. The first breakthrough was Nα-guanylhistamine, a partial H2-receptor antagonist. From this lead the receptor model was further refined and eventually led to the development of burimamide, the first H2-receptor antagonist. Burimamide, a specific competitive antagonist at the H2-receptor 100-times more potent than Nα-guanylhistamine, proved the existence of the H2-receptor.
Burimamide was still insufficiently potent for oral administration and further modification of the structure, based on modifying the pKa of the compound, lead to the development of metiamide. Metiamide was an effective agent, however it was associated with unacceptable nephrotoxicity and agranulocytosis. It was proposed that the toxicity arose from the thiourea group, and similar guanidine-analogues were investigated until the ultimate discovery of cimetidine.
Cimetidine was first marketed in the United Kingdom in 1976; therefore, it took 12 years from initiation of the H2-receptor antagonist program to commercialization. Subsequent to the introduction onto the U.S. drug market, two other H2-receptor antagonists were approved, ranitidine (Zantac, Glaxo Labs) and famotidine (Pepcid, Yamanouchi, Ltd.) Cimetidine became the first drug ever to reach more than $1 billion a year in sales, thus making it the first blockbuster drug.[2]
Recreational Use
It is believed that consuming Cimetidine an hour before smoking Cannabis, would potentate the Cannabis's effects.[citation needed] It is believed because Cimetidine inhibits the CYP-450 enzyme, and metabolism mainly occurs in the liver by cytochrome P450 enzymes CYP2C9, CYP2C19, and CYP3A4. Due to the inhibition of the CYP-450 enzyme, THC, the psychoactive substance in Cannabis, would not be able to be metabolized until the inhibition of the CYP-450 enzyme is lifted, which may take hours, thus increasing the duration of its effect.
Other uses
In some studies, cimetidine has been found to reduce the debilitating pain and symptoms of herpes zoster, presumably by blocking the H2-receptors of T-lymphocyte suppressor cells.[3]
A number of "open label" studies showed that cimetidine was effective in the treatment of common warts, but more rigorous double-blinded clinical trials showed it to be no more effective than a placebo. [4]
Another study by Yokoyama et al. used Cimetidine for the treatment of chronic calcific tendinitis of the shoulder.[5] The small scale study took 16 individuals with calcific tendinitis in one shoulder, all of which had previously attempted other forms of therapy including steroid injection and arthroscopic lavage. During the course of the study 10 patients reported an elimination of pain and 9 displayed a complete disappearance of Calcium deposits. With results being on a small scale, it has been recommended that Cimetidine, for the treatment of chronic calcific tendinitis of the shoulder, be opened to large scale clinical trials. [6]
Cimetidine has also been reported[7] for use in treatment of colorectal cancer - it is however not approved in the US by the FDA for cancer treatment.
Cimetidine has been reported for use as an analgesic in experimental treatments of interstitial cystitis.
Pretreatment with cimetidine improves the accuracy of measured creatinine clearance testing when using urine collection analysis.
Shortcomings and side effects
Cimetidine is a known inhibitor of many isozymes of the cytochrome P450 enzyme system[8] (specifically CYP1A2, CYP2C9, CYP2C19, CYP2D6, CYP2E1, and CYP3A4). This inhibition forms the basis of the numerous drug interactions that occur between cimetidine and other drugs. For example, cimetidine may decrease metabolism of some drugs, such as those used in hormonal contraception. Cimetidine interferes with metabolism of the hormone estrogen, enhancing estrogen activity. In women, this can lead to galactorrhea, whereas in men gynecomastia[9]. Cimetidine also affects the metabolism of methadone, sometimes resulting in higher blood levels and a higher incidence of side effects. Adverse drug reactions were also found to be relatively common with Cimetidine, including interactions with the antimalarial medication Hydroxychloroquine[citation needed].
The development of longer-acting H2-receptor antagonists with reduced adverse effects such as ranitidine proved to be the downfall of cimetidine and, whilst it is still used, it is no longer amongst the more widely used H2-receptor antagonists. Side effects can include dizziness, and more rarely, headache.
References
- ^ Silverman, Richard A. (2004). The organic chemistry of drug design and drug action. Amsterdam: Elsevier Academic Press. p. 159. ISBN 0-12-643732-7.
- ^ Whitney, Jake (February 2006). "Pharmaceutical Sales 101: Me-Too Drugs". Guernica. http://www.guernicamag.com/features/111/me_too_drugs/. Retrieved on 2008-07-31.
- ^ Faloon, William; Kitchen, Kate (March 2001). "Tagemet to Treat Herpes and Shingles". Life Extension Magazine. http://www.lef.org/magazine/mag2001/mar2001_report_tagamet_1.html. Retrieved on 2009-03-05.
- ^ Fit KE, Williams PC (Jul 2007). "Use of histamine2-antagonists for the treatment of verruca vulgaris". Ann Pharmacother 41 (7): 1222–6. doi:. PMID 17535844.
- ^ Yokoyama M, Aono H, Takeda A, Morita K (2003). "Cimetidine for chronic calcifying tendinitis of the shoulder". Reg Anesth Pain Med 28 (3): 248–52. doi:. PMID 12772145.
- ^ "Musculoskeletal Pain". http://www.pain.com/sections/categories_of_pain/Musculoskeletal/resources/library/abstract.cfm?ID=5248&next_page=1&startrec=1&RecordDisplays=20&Search_phrase=shoulder. Retrieved on 2008-10-22.
- ^ "Colorectal Cancer - Page 2 Of 3: Online References For Health Concerns". http://www.lef.org/protocols/cancer/colorectal_02.htm+. Retrieved on 2008-10-22.
- ^ Levine M, Law EY, Bandiera SM, Chang TK, Bellward GD (Feb 1998). "In vivo cimetidine inhibits hepatic CYP2C6 and CYP2C11 but not CYP1A1 in adult male rats". The Journal of pharmacology and experimental therapeutics 284 (2): 493–9. PMID 9454789. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=9454789.
- ^ Michnovicz JJ, Galbraith RA (Feb 1991). "Cimetidine inhibits catechol estrogen metabolism in women". Metabolism: clinical and experimental 40 (2): 170–4. PMID 1988774.
External links
- American Chemical Society - National Historic Chemical Landmarks - Tagamet: A medicine that changed people's lives
- Tagamet HB200
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