ChemFOnt: Showing chemical card for Cimetidine (CFc000009001)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:00 UTC

Chemfont ID

CFc000009001

Molecule Identification

Common Name

Cimetidine

Definition

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. [PubChem]

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 Weight

252.339

Monoisotopic Molecular Weight

252.115715232

IUPAC Name

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

Traditional Name

tagamet HB

CAS Registry Number

51481-61-9

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 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014644)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Cimetidine Pathway (HMDB: HMDB0014644)
Cimetidine Action Pathway (PathBank: SMP0000232)

Metabolic pathway

Cimetidine Metabolism Pathway (PathBank: SMP0000617)

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Analgesic (HMDB: HMDB0014644)
Adjuvant (HMDB: HMDB0014644)

H2-receptor antagonist (HMDB: HMDB0014644)

Pharmaceutical industry

Anti-ulcer drug (HMDB: HMDB0014644)

Biological role

Modulator

Inhibitor

P450 inhibitor (HMDB: HMDB0014644)

Physical Properties

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon