Cimetidine (CHEM002212)

Record Information
Version1.0
Creation Date2009-07-21 20:27:02 UTC
Update Date2026-05-14 16:40:36 UTC
Accession NumberCHEM002212
Identification
Common NameCimetidine
ClassSmall Molecule
Description
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 gastrins output. It also blocks the activity of cytochrome P-450 which might explain proposals for use in neoadjuvant therapy.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • Suspected Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Adjuvant
  • Amide
  • Amine
  • Analgesic
  • Anti-Ulcer Agent
  • Drug
  • Enzyme Inhibitor
  • Ether
  • Histamine Antagonist
  • Histamine H2 Antagonist
  • Human Neurotoxin
  • Metabolite
  • Nitrile
  • Organic Compound
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Cyano-2-methyl-3-(2-(((5-methyl-4-imidazolyl)methyl)thio)ethyl)guanidineChEBI
2-Cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)guanidineChEBI
CimetagChEBI
CimetidinaChEBI
CimetidinumChEBI
N''-cyano-N-methyl-n'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]thio}ethyl)guanidineChEBI
N-Cyano-n'-methyl-n''-(2-([(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl)ethyl)guanidineChEBI
Tagamet HB 200ChEBI
UlcerfenChEBI
TagametKegg
N-Cyano-n'-methyl-n''-(2-([(5-methyl-1H-imidazol-4-yl)methyl]sulphanyl)ethyl)guanidineGenerator
Cimetidine HCLHMDB
EureceptorHMDB
HistodilHMDB
SK And F92334HMDB
BiometHMDB
Cimetidine hydrochlorideHMDB
HCL, CimetidineHMDB
Hydrochloride, cimetidineHMDB
N-Cyano-n'-methyl-n''-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl)guanidineHMDB
SK And F 92334HMDB
SK And F-92334HMDB
AltrametHMDB
Biomet400HMDB
Chemical FormulaC10H16N6S
Average Molecular Mass252.339 g/mol
Monoisotopic Mass252.116 g/mol
CAS Registry Number51481-61-9
IUPAC Name(Z)-N-cyano-N''-methyl-N'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine
Traditional Nametagamet HB
SMILESC\N=C(\NCCSCC1=C(C)NC=N1)NC#N
InChI IdentifierInChI=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)
InChI KeyAQIXAKUUQRKLND-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentImidazoles
Alternative Parents
Substituents
  • Imidazole
  • Heteroaromatic compound
  • Guanidine
  • Thioether
  • Carboximidamide
  • Sulfenyl compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Dialkylthioether
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Imine
  • Organonitrogen compound
  • Organosulfur compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Cimetidine PathwayNot AvailableNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point142°C
Boiling PointNot Available
Solubility9380 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP0.44ALOGPS
logP-0.11ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)13.38ChemAxon
pKa (Strongest Basic)6.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area88.89 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity70.32 m³·mol⁻¹ChemAxon
Polarizability27.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral, rapid 60-70%
Mechanism of ToxicityCimetidine binds to an H2-receptor located on the basolateral membrane of the gastric parietal cell, blocking histamine effects. This competitive inhibition results in reduced gastric acid secretion and a reduction in gastric volume and acidity.
MetabolismHepatic Route of Elimination: The principal route of excretion of cimetidine is the urine. Half Life: 2 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (2)
Uses/SourcesFor the treatment and the management of acid-reflux disorders (GERD), peptic ulcer disease, heartburn, and acid indigestion.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include nausea, vomiting, diarrhea, increased saliva production, difficulty breathing, and a fast heartbeat.
TreatmentThe usual measures to remove unabsorbed material from the gastrointestinal tract, clinical monitoring and supportive therapy should be employed. (4)
Concentrations
Not Available
External Links
DrugBank IDDB00501
HMDB IDHMDB0014644
FooDB IDFDB010095
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCimetidine
Chemspider ID2654
ChEBI ID3699
PubChem Compound ID2756
Kegg Compound IDC06952
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Saburo Uchikuga, Tomoyasu Tashiro, Yasuko Osawa, “Process for preparing the H.sub.2 -receptor antagonist cimetidine.” U.S. Patent US4413129, issued March, 1972.

MSDSLink
General References
1. Michnovicz JJ, Galbraith RA: Cimetidine inhibits catechol estrogen metabolism in women. Metabolism. 1991 Feb;40(2):170-4.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11910267
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15637527
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=7229121