Cimetidine

Cimetidine
Clinical data
Pronunciation/sɪˈmɛtɪdiːn/ or /saɪˈmɛtɪdiːn/
Trade namesTagamet, others
Other namesSKF-92334[1]
AHFS/Drugs.comMonograph
MedlinePlusa682256
License data
Pregnancy
category
  • AU: B1
Routes of
administration		By mouth, intramuscular injection, intravenous infusion[2]
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability60–70%[5][6]
Protein binding13–25%[6][7]
MetabolismLiver[6]
Metabolites• Cimetidine sulfoxide[6]
• Hydroxycimetidine[6]
• Guanyl urea cimetidine[6]
Onset of action30 minutes[8]
Elimination half-life123 minutes (~2 hours)[7]
Duration of action4–8 hours[2]
ExcretionUrine[7]
Identifiers
IUPAC name
  • 1-cyano-2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.052.012
Chemical and physical data
FormulaC10H16N6S
Molar mass252.34 g·mol−1
3D model (JSmol)
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) Y
  • Key:AQIXAKUUQRKLND-UHFFFAOYSA-N Y
  (verify)

Cimetidine, sold under the brand name Tagamet among others, is a histamine H2 receptor antagonist that inhibits stomach acid production.[1][9][10] It is mainly used in the treatment of heartburn and peptic ulcers.[1][10][11]

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.[12]

Cimetidine was developed in 1971 and came into commercial use in 1977.[13][14] Cimetidine was approved in the United Kingdom in 1976, and was approved in the United States by the Food and Drug Administration in 1979.[15]

  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. ^ "Cimetidine tablet, film coated". DailyMed. 30 November 2022. Retrieved 24 June 2024.
  4. ^ "Tagamet - cimetidine tablet". DailyMed. 10 June 2024. Retrieved 24 June 2024.
  5. ^ 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.
  6. ^ a b c d e f Cite error: The named reference LeikinPaloucek1995 was invoked but never defined (see the help page).
  7. ^ a b c Profiles of Drug Substances, Excipients and Related Methodology. Academic Press. 24 October 1984. pp. 176–. ISBN 978-0-08-086108-1.
  8. ^ Cite error: The named reference VallerandSanoski2016 was invoked but never defined (see the help page).
  9. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 234–. ISBN 978-3-88763-075-1.
  10. ^ 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.
  11. ^ 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.
  12. ^ 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.
  13. ^ Fischer J, Ganellin CR (24 August 2010). Analogue-based Drug Discovery II. John Wiley & Sons. p. 4. ISBN 978-3-527-63212-1.
  14. ^ 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.
  15. ^ "Tagamet: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 30 April 2017. Retrieved 9 November 2023.
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