cimetidine

Also known as cimetidine HCl, Tagamet®, 1-Cyano-2-methyl-3-(2-(((5-methyl-4-imidazolyl)methyl)thio)ethyl)guanidine, N''-cyano-N-methyl-N'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]thio}ethyl)guanidine, N-cyano-N'-methyl-N''-(2-([(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl)ethyl)guanidine, 2-cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)guanidine, Tagamet hb 200, Cimetidinum

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

Key facts

Drug.pregnancy_AU: B1
Drug.routes_of_administration: By mouth, intramuscular injection, intravenous infusion
Drug.ATC_prefix: A02
Drug.ATC_suffix: BA01
Drug.legal_AU: S4
Drug.legal_UK: POM
Drug.legal_US: Rx-only
Drug.legal_US_comment: / OTC
Drug.bioavailability: 60–70%
Drug.protein_bound: 13–25%
Drug.metabolism: Liver
Drug.Watchedfields: changed
Drug.verifiedrevid: 456484490
Drug.image: Cimetidine.svg
Drug.image_class: skin-invert-image
Drug.width: 250
Drug.image2: Cimetidine-xtal-3D-balls.png
Drug.image_class2: bg-transparent

via Wikipedia infobox

Chemical data

Formula: C10H16N6S
Molecular weight: 252.34 g/mol
IUPAC name: 1-cyano-2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine
SMILES: CC1=C(N=CN1)CSCCNC(=NC)NC#N
InChIKey: AQIXAKUUQRKLND-UHFFFAOYSA-N
XLogP: 0.4
Polar surface area: 114 Å²
H-bond donors: 3
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

12,893 papers

Cimetidine.IARC monographs on the evaluation of carcinogenic risks to humans · 1990
Cimetidine: an immunomodulator.DICP : the annals of pharmacotherapy · 1990
Cimetidine.South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde · 1978
Cimetidine in dermatology.International journal of dermatology · 1987
Cimetidine.JAMA · 1978

via PubMed

Wikidata facts

Mass: 252.115716

Show 5 more facts

Commons category: Cimetidine
chemical formula: C₁₀H₁₆N₆S
canonical SMILES: CC1=C(N=CN1)CSCCNC(=NC)NC#N
isomeric SMILES: CN/C(=N\CCSCC=1N=CNC1C)/NC#N
World Health Organisation international non-proprietary name: cimetidine

Sources (5)

via Wikidata · CC0

~17 min read

Article

16 sections

Contents

Medical uses
Side effects
Overdose
Interactions
Pharmacology
Pharmacodynamics
Histamine H<sub>2</sub> receptor antagonism
Cytochrome P450 inhibition
Antiandrogenic and estrogenic effects
Pharmacokinetics
History
Lawsuit
Research
Veterinary use
References
External links

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.