ContaminantDB: Cimetidine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:02 UTC

Update Date

2026-03-31 17:03:14 UTC

Accession Number

CHEM002212

Identification

Common Name

Cimetidine

Class

Small 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
Metabolite
Nitrile
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Cyano-2-methyl-3-(2-(((5-methyl-4-imidazolyl)methyl)thio)ethyl)guanidine	ChEBI
2-Cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)guanidine	ChEBI
Cimetag	ChEBI
Cimetidina	ChEBI
Cimetidinum	ChEBI
N''-cyano-N-methyl-n'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]thio}ethyl)guanidine	ChEBI
N-Cyano-n'-methyl-n''-(2-([(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl)ethyl)guanidine	ChEBI
Tagamet HB 200	ChEBI
Ulcerfen	ChEBI
Tagamet	Kegg
N-Cyano-n'-methyl-n''-(2-([(5-methyl-1H-imidazol-4-yl)methyl]sulphanyl)ethyl)guanidine	Generator
Cimetidine HCL	HMDB
Eureceptor	HMDB
Histodil	HMDB
SK And F92334	HMDB
Biomet	HMDB
Cimetidine hydrochloride	HMDB
HCL, Cimetidine	HMDB
Hydrochloride, cimetidine	HMDB
N-Cyano-n'-methyl-n''-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl)guanidine	HMDB
SK And F 92334	HMDB
SK And F-92334	HMDB
Altramet	HMDB
Biomet400	HMDB

Chemical Formula

C₁₀H₁₆N₆S

Average Molecular Mass

252.339 g/mol

Monoisotopic Mass

252.116 g/mol

CAS Registry Number

51481-61-9

IUPAC Name

(Z)-N-cyano-N''-methyl-N'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine

Traditional Name

tagamet HB

SMILES

C\N=C(\NCCSCC1=C(C)NC=N1)NC#N

InChI Identifier

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)

InChI Key

AQIXAKUUQRKLND-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Imidazoles

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:3699 )
guanidines (CHEBI:3699 )
aliphatic sulfide (CHEBI:3699 )
nitrile (CHEBI:3699 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Cimetidine Pathway	Not Available	Not Available

Applications

Biological Roles

Chemical Roles

P450 inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	142°C
Boiling Point	Not Available
Solubility	9380 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.82 g/L	ALOGPS
logP	0.44	ALOGPS
logP	-0.11	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	13.38	ChemAxon
pKa (Strongest Basic)	6.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.89 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	70.32 m³·mol⁻¹	ChemAxon
Polarizability	27.47 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-9500000000-8ff5fa28797a788c95be	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0002-9511000000-75fc9243ad1eb9c79cb4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4j-5900000000-122f9dbdf583bbe3dee8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0002-9300000000-39ee157d9e264867cfa4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0002-9000000000-6e876a668444c8277412	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0002-9000000000-85640be9b2799889fd02	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0002-9000000000-9b8d3eafde213bee6396	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4j-9000000000-b47e11697992a843f5e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4i-9000000000-75ebe86c90f5ed341c57	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0aor-9000000000-d7302885bef7454b4db2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-014i-9000000000-b2f3ab1b5ae1e2f8f8bb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0930000000-dbae8348b5c999cc664d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-052b-9600000000-8b4b94cd7303c9b9a0ef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9000000000-c23b62afdf4dff8c43db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9000000000-e477cd71a628f6adaf46	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-052e-9000000000-61584ad991262d50a01b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0zfr-1980000000-84e04b032e6f422e5b6b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0aos-2900000000-e8d9297512335ce612fb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-052b-9800000000-7235208cf21d7ea1f7ad	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9300000000-4996f6630fe29fccd7d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ufs-7790000000-535b3b79ad51bbf5a724	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056s-5910000000-059a8f3e3eb08432dd72	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9100000000-ceadcc70f9905df3cd1b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ufs-7960000000-d054508682ae0a8a700d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0adm-5910000000-05af2f300dae46b29b5f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-43451f5e853f064cd924	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-002b-9510000000-36ce01132725fd5bf5d8	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral, rapid 60-70%

Mechanism of Toxicity

Cimetidine 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.

Metabolism

Hepatic Route of Elimination: The principal route of excretion of cimetidine is the urine. Half Life: 2 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (2)

Uses/Sources

For the treatment and the management of acid-reflux disorders (GERD), peptic ulcer disease, heartburn, and acid indigestion.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include nausea, vomiting, diarrhea, increased saliva production, difficulty breathing, and a fast heartbeat.

Treatment

The 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 ID

DB00501

HMDB ID

HMDB0014644

FooDB ID

FDB010095

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not 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.

MSDS

Link

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

Cimetidine (CHEM002212)

Structure for CHEM002212: Cimetidine