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Substance Name: Cimetidine [USAN:USP:INN:BAN:JAN]
RN: 51481-61-9
UNII: 80061L1WGD
InChIKey: AQIXAKUUQRKLND-UHFFFAOYSA-N

Note

  • A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.

Molecular Formula

  • C10-H16-N6-S

Molecular Weight

  • 252.3444
 

Classification Codes

Classification Codes

  • Antagonist (to Histamine H2 Receptors)
  • Anti-Ulcer Agents
  • Cytochrome P-450 CYP1A2 Inhibitors
  • Cytochrome P-450 Enzyme Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Gastrointestinal Agents
  • Histamine Agents
  • Histamine Antagonists
  • Histamine H2 Antagonists
  • Human Data
  • Metabolic Side Effects of Drugs and Substances
  • Mutation Data
  • Neurotransmitter Agents
  • Reproductive Effect
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • Cimetidine
  • Cimetidine [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Cimetidine

Synonyms

  • 1-Cyano-2-methyl-3-(2-(((5-methyl-4-imidazolyl)methyl)thio)ethyl)guanidine
  • 2-Cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)guanidine
  • Acibilin
  • Acinil
  • CCRIS 3247
  • Cimal
  • Cimetag
  • Cimetidina
  • Cimetidina [INN-Spanish]
  • Cimetidine
  • Cimetidinum
  • Cimetidinum [INN-Latin]
  • Cimetum
  • DRG-0150
  • Dyspamet
  • Edalene
  • EINECS 257-232-2
  • Equaline acid reducer
  • Eureceptor
  • Evicer
  • Gastrobitan
  • Gastromet
  • Guanidine, N-cyano-N'-methyl-N''-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio) ethyl)-
  • HSDB 3917
  • Metracin
  • N-Cyano-N'-methyl-N''-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl)guanidine
  • SKF 92334
  • Tagamet
  • Tagamet HB
  • Tagamet HB 200
  • Tametin
  • Topcare heartburn relief
  • Tratul
  • Ulcedin
  • Ulcedine
  • Ulcestop
  • Ulcimet
  • Ulcomet
  • Ulhys
  • UNII-80061L1WGD
  • Valmagen

Systematic Names

  • Cimetidine
  • 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)thio)ethyl)-

Superlist Name

  • Cimetidine

Registry Numbers

CAS Registry Number

  • 51481-61-9

FDA UNII

  • 80061L1WGD

System Generated Number

  • 0051481619

Structure Descriptors

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)

InChIKey

AQIXAKUUQRKLND-UHFFFAOYSA-N

Smiles

Cc1c(nc[nH]1)CSCCN/C(=N/C#N)/NC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo intravenous 100mg/kg (100mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP Annals of Internal Medicine. Vol. 97, Pg. 283, 1982.
dog LD50 intravenous 206mg/kg (206mg/kg) GASTROINTESTINAL: OTHER CHANGES

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Kiso to Rinsho. Clinical Report. Vol. 14, Pg. 2806, 1980.
dog LD50 oral 2600mg/kg (2600mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 1, Pg. 329, 1977.
hamster LD50 intraperitoneal 880mg/kg (880mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Gastroenterology. Vol. 74, Pg. 339, 1978.
hamster LD50 oral 4gm/kg (4000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Gastroenterology. Vol. 74, Pg. 339, 1978.
human TDLo oral 80mg/kg/8D (80mg/kg) BLOOD: LEUKOPENIA

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Lancet. Vol. 1, Pg. 444, 1978.
man TDLo intravenous 4286ug/kg/30M (4.286mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER
Annals of Internal Medicine. Vol. 97, Pg. 374, 1982.
man TDLo oral 2857ug/kg (2.857mg/kg) CARDIAC: OTHER CHANGES Lancet. Vol. 1, Pg. 225, 1987.
man TDLo oral 51mg/kg/3D-I (51mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" American Journal of Medicine. Vol. 75, Pg. 875, 1983.
man TDLo oral 57mg/kg/5D-I (57mg/kg) LIVER: "JAUNDICE, CHOLESTATIC" Digestive Diseases and Sciences. Vol. 32, Pg. 333, 1987.
man TDLo oral 270mg/kg/3W-I (270mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS
American Journal of Medicine. Vol. 70, Pg. 1272, 1981.
man TDLo unreported 600mg/kg/6W (600mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER Lancet. Vol. 1, Pg. 1160, 1981.
mouse LD50 intraperitoneal 306mg/kg (306mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 1655, 1983.
mouse LD50 intravenous 150mg/kg (150mg/kg)   Journal of International Medical Research. Vol. 3, Pg. 86, 1975.
mouse LD50 oral 2550mg/kg (2550mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 1685, 1983.
mouse LD50 subcutaneous 437mg/kg (437mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 1685, 1983.
rabbit LD50 intraperitoneal 1063mg/kg (1063mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 1685, 1983.
rabbit LD50 intravenous 164mg/kg (164mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 1685, 1983.
rabbit LD50 oral > 8640mg/kg (8640mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 1685, 1983.
rat LD50 intraperitoneal 328mg/kg (328mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 1685, 1983.
rat LD50 intravenous 106mg/kg (106mg/kg)   Journal of International Medical Research. Vol. 3, Pg. 86, 1975.
rat LD50 oral 5gm/kg (5000mg/kg)   Journal of International Medical Research. Vol. 3, Pg. 86, 1975.
rat LD50 subcutaneous 860mg/kg (860mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 1685, 1983.
women LDLo intravenous 1008mg/kg/6W- (1008mg/kg) VASCULAR: OTHER CHANGES Drug Intelligence and Clinical Pharmacy. Vol. 17, Pg. 126, 1983.
women TDLo intravenous 4mg/kg/2M-C (4mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP Lancet. Vol. 1, Pg. 99, 1987.
women TDLo oral 30mg/kg/2D-I (30mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: REGIDITY

BEHAVIORAL: ATAXIA
Annals of Emergency Medicine. Vol. 16, Pg. 1162, 1987.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 142 deg C   EXP
pKa Dissociation Constant 6.8 (none)   EXP
log P (octanol-water) 0.4 (none)   EXP
Water Solubility 9380 mg/L 25 EXP
Vapor Pressure 5.50E-09 mm Hg 25 EST
Henry's Law Constant 9.50E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.10E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.