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Cimetidine information


Cimetidine
Clinical data
Pronunciation/sɪˈmɛtɪdn/ or /sˈmɛtɪdn/
Trade namesTagamet, others
Other namesSKF-92334[1]
AHFS/Drugs.comMonograph
MedlinePlusa682256
License data
  • US DailyMed: Cimetidine
Pregnancy
category
  • AU: B1
Routes of
administration
By mouth, intramuscular injection, intravenous infusion[2]
ATC code
  • A02BA01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only / OTC
Pharmacokinetic data
Bioavailability60–70%[3][4]
Protein binding13–25%[4][5]
MetabolismLiver[4]
Metabolites• Cimetidine sulfoxide[4]
• Hydroxycimetidine[4]
• Guanyl urea cimetidine[4]
Onset of action30 minutes[6]
Elimination half-life123 minutes (~2 hours)[5]
Duration of action4–8 hours[2]
ExcretionUrine[5]
Identifiers
IUPAC name
  • 1-cyano-2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine
CAS Number
  • 51481-61-9 checkY
PubChem CID
  • 2756
IUPHAR/BPS
  • 1231
DrugBank
  • DB00501 checkY
ChemSpider
  • 2654 checkY
UNII
  • 80061L1WGD
KEGG
  • D00295 checkY
ChEBI
  • CHEBI:3699 checkY
ChEMBL
  • ChEMBL30 checkY
CompTox Dashboard (EPA)
  • DTXSID4020329 Edit this at Wikidata
ECHA InfoCard100.052.012 Edit this at Wikidata
Chemical and physical data
FormulaC10H16N6S
Molar mass252.34 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CC1=C(N=CN1)CSCCNC(=NC)NC#N
InChI
  • InChI=1S/C10H16N6S/c1-8-9(16-7-15-8)5-17-4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14) checkY
  • Key:AQIXAKUUQRKLND-UHFFFAOYSA-N checkY
  (verify)

Cimetidine, sold under the brand name Tagamet among others, is a histamine H2 receptor antagonist that inhibits stomach acid production.[1][7][8] It is mainly used in the treatment of heartburn and peptic ulcers.[1][8][9]

With the development of proton pump inhibitors, such as omeprazole, approved for the same indications, cimetidine is available as an over-the-counter formulation to prevent heartburn or acid indigestion, along with the other H2-receptor antagonists.[10]

Cimetidine was developed in 1971 and came into commercial use in 1977.[11][12] Cimetidine was approved in the United Kingdom in 1976,[citation needed] and was approved in the United States by the Food and Drug Administration in 1979.[13]

  1. ^ a b c Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Bibliographies. Springer. pp. 275–. ISBN 978-1-4757-2085-3.
  2. ^ a b Gupta A, Singh-Radcliff N (12 March 2013). Pharmacology in Anesthesia Practice. Oxford University Press. pp. 177–. ISBN 978-0-19-934399-7.
  3. ^ Dowd FJ, Johnson B, Mariotti A (3 September 2016). Pharmacology and Therapeutics for Dentistry - E-Book. Elsevier Health Sciences. pp. 406–. ISBN 978-0-323-44595-5.
  4. ^ a b c d e f Cite error: The named reference LeikinPaloucek1995 was invoked but never defined (see the help page).
  5. ^ a b c Profiles of Drug Substances, Excipients and Related Methodology. Academic Press. 24 October 1984. pp. 176–. ISBN 978-0-08-086108-1.
  6. ^ Cite error: The named reference VallerandSanoski2016 was invoked but never defined (see the help page).
  7. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 234–. ISBN 978-3-88763-075-1.
  8. ^ a b Morton I, Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 77–. ISBN 978-0-7514-0499-9.
  9. ^ Jacqueline B, Rosenthal L (2 December 2014). "Drugs for Peptic Ulcer Disease". Lehne's Pharmacology for Nursing Care. Elsevier Health Sciences. pp. 952–. ISBN 978-0-323-34026-7.
  10. ^ Pino MA, Azer SA (March 2023). "Cimetidine". StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing. PMID 31334975. Bookshelf ID: NBK544255. Retrieved 6 November 2023 – via U.S. National Library of Medicine.
  11. ^ Fischer J, Ganellin CR (24 August 2010). Analogue-based Drug Discovery II. John Wiley & Sons. p. 4. ISBN 978-3-527-63212-1.
  12. ^ Alapi EM, Fischer J (2006). "Table of Selected Analogue Classes". In Fischer J, Ganellin CR (eds.). Analogue-based Drug Discovery. John Wiley & Sons. p. 444. ISBN 9783527607495.
  13. ^ "Tagamet: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 9 November 2023.

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Cimetidine

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Cimetidine, sold under the brand name Tagamet among others, is a histamine H2 receptor antagonist that inhibits stomach acid production. It is mainly used...

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H2 receptor antagonist

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of ulcers and reflux oesophagitis than the H2 blockers ranitidine and cimetidine. H2 antagonists, which all end in "-tidine", are a type of antihistamine...

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Molluscum contagiosum

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blistering are common. There is no high-quality evidence for cimetidine. However, oral cimetidine has been used as an alternative treatment for the pediatric...

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Porphyria

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progressing to bulbar paresis and respiratory paralysis.[citation needed] Cimetidine has also been reported to be effective for acute porphyric crisis and...

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Famotidine

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parietal cells, ultimately reducing acid secretion into the stomach. Unlike cimetidine, the first H2 antagonist, famotidine has a minimal effect on the cytochrome...

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Galactorrhea

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associated with the use of the second-generation H2 receptor antagonist cimetidine (Tagamet). Galactorrhea can also be caused by antipsychotics that cause...

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Praziquantel

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praziquantel. Chloroquine also reduces its bioavailability. The drug cimetidine heightens praziquantel bioavailability. The drug's mode of action is not...

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Albendazole

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and half-life of albendazole sulfoxide's R(+) enantiomer. The antacid cimetidine heightens serum albendazole concentrations, increases the half-life of...

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Tizanidine

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certain antiarrhythmics (amiodarone, mexiletine, propafenone, verapamil), cimetidine, famotidine, aciclovir, ticlopidine and oral contraceptives) is contraindicated...

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Dermatographic urticaria

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of H1 antagonists, or possibly with an H2-receptor antagonist such as cimetidine. Over-the-counter vitamin C, 1000 mg daily, increases histamine degradation...

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Loratadine

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as inhibitors of the CYP3A4 enzyme such as ketoconazole, erythromycin, cimetidine, and furanocoumarin derivatives (found in grapefruit) lead to increased...

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Antihistamine

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receptors. Cimetidine, for example, is notorious for antagonizing androgenic testosterone and DHT receptors at high doses. Examples include: Cimetidine Famotidine...

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Amitriptyline

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changes occur with a moderate inhibitor of CYP2C19 and other cytochromes cimetidine: amitriptyline level increases by about 70%, while nortriptyline decreases...

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Cefalexin

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concentrations of metformin in the body. Histamine H2 receptor antagonists like cimetidine and ranitidine may reduce the efficacy of cefalexin by delaying its absorption...

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Lornoxicam

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in patients with special risks like heart failure. As with piroxicam, cimetidine can increase plasma levels but is unlikely to cause relevant interactions...

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Sinus bradycardia

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blockers, class I antiarrhythmic agents, ivabradine, clonidine, reserpine, cimetidine, lithium, amitriptyline Diagnosis of sinus bradycardia can be confirmed...

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Equine melanoma

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resolve tumors with or without surgical removal for at least 2 years. Cimetidine works by slowing tumor growth; it is a histamine blocker that maintains...

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Phenylbutazone

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and carprofen). Gastrointestinal-protectant drugs, such as misoprostol, cimetidine, omeprazole, ranitidine, or sucralfate, are frequently included as a part...

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ATC code A02

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antiflatulents A02AF02 Ordinary salt combinations and antiflatulents A02BA01 Cimetidine A02BA02 Ranitidine A02BA03 Famotidine A02BA04 Nizatidine A02BA05 Niperotidine...

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Timeline of peptic ulcer disease and Helicobacter pylori

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Marshall and Ian Hislop begin a study to compare bismuth treatment with cimetidine. The study is abandoned because it is inconclusive. June: Warren and Marshall's...

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Fecal occult blood

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hypertonic liquids, and lessened by adequate training. Ingestion of 800 mg of cimetidine two hours before running a marathon did not significantly affect the frequency...

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Metiamide

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intermediate compound in the development of the successful anti-ulcer drug cimetidine (Tagamet). After discovering that burimamide is largely inactive at physiological...

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Dimenhydrinate

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HTMT Impromidine L-Histidine UR-AK49 Antagonists Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Isolamtidine Lafutidine...

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Fexofenadine

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HTMT Impromidine L-Histidine UR-AK49 Antagonists Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Isolamtidine Lafutidine...

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Metformin

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metformin and cimetidine are cleared from the body by tubular secretion, and both, particularly the cationic (positively charged) form of cimetidine, may compete...

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Metandienone

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Potassium canrenoate Spironolactone Nonsteroidal: Apalutamide Bicalutamide Cimetidine Darolutamide Enzalutamide Flutamide Ketoconazole Nilutamide Seviteronel†...

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Rebamipide

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reduces relapse of acetic acid-induced rat gastric ulcer. Comparison with cimetidine". Digestive Diseases and Sciences. 40 (11): 2469–72. doi:10.1007/bf02063257...

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Betahistine

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HTMT Impromidine L-Histidine UR-AK49 Antagonists Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Isolamtidine Lafutidine...

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