Cimetidine

Cimetidine
Clinical data
Pronunciation	/sɪˈmɛtɪdiːn/ or /saɪˈmɛtɪdiːn/
Trade names	Tagamet, others
Other names	SKF-92334
AHFS/Drugs.com	Monograph
MedlinePlus	a682256
License data	US DailyMed: Cimetidine;
Pregnancy; category	AU: B1;
Routes of; administration	By mouth, intramuscular injection, intravenous infusion
ATC code	A02BA01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only / OTC;
Pharmacokinetic data
Bioavailability	60–70%
Protein binding	13–25%
Metabolism	Liver
Metabolites	• Cimetidine sulfoxide; • Hydroxycimetidine; • Guanyl urea cimetidine
Onset of action	30 minutes
Elimination half-life	123 minutes (~2 hours)
Duration of action	4–8 hours
Excretion	Urine
Identifiers
	IUPAC name 1-cyano-2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine;
CAS Number	51481-61-9 ;
PubChem CID	2756;
IUPHAR/BPS	1231;
DrugBank	DB00501 ;
ChemSpider	2654 ;
UNII	80061L1WGD;
KEGG	D00295 ;
ChEBI	CHEBI:3699 ;
ChEMBL	ChEMBL30 ;
CompTox Dashboard (EPA)	DTXSID4020329 ;
ECHA InfoCard	100.052.012
Chemical and physical data
Formula	C10H16N6S
Molar mass	252.34 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) ; Key:AQIXAKUUQRKLND-UHFFFAOYSA-N ;
	(verify)

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.

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.

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

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