CHEBI:3699 - cimetidine

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ChEBI Name cimetidine
ChEBI ID CHEBI:3699
Definition A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H2-receptor antagonist that inhibits the production of acid in stomach.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C10H16N6S
Net Charge 0
Average Mass 252.34048
Monoisotopic Mass 252.116
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)
InChIKey AQIXAKUUQRKLND-UHFFFAOYSA-N
SMILES CN\C(NCCSCc1nc[nH]c1C)=N\C#N
Roles Classification
Biological Role(s): H2-receptor antagonist
H2-receptor antagonists are the drugs that selectively bind to but do not activate histamine H2 receptors, thereby blocking the actions of endogenous histamine.
P450 inhibitor
An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.
analgesic
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
Application(s): H2-receptor antagonist
H2-receptor antagonists are the drugs that selectively bind to but do not activate histamine H2 receptors, thereby blocking the actions of endogenous histamine.
analgesic
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
adjuvant
Any pharmacological or immunological agent that modifies the effect of other agents such as drugs or vaccines while having few if any direct effects when given by itself.
anti-ulcer drug
One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.
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ChEBI Ontology
Outgoing cimetidine (CHEBI:3699) has role adjuvant (CHEBI:60809)
cimetidine (CHEBI:3699) has role analgesic (CHEBI:35480)
cimetidine (CHEBI:3699) has role anti-ulcer drug (CHEBI:49201)
cimetidine (CHEBI:3699) has role H2-receptor antagonist (CHEBI:37961)
cimetidine (CHEBI:3699) has role P450 inhibitor (CHEBI:50183)
cimetidine (CHEBI:3699) is a aliphatic sulfide (CHEBI:22327)
cimetidine (CHEBI:3699) is a guanidines (CHEBI:24436)
cimetidine (CHEBI:3699) is a imidazoles (CHEBI:24780)
cimetidine (CHEBI:3699) is a nitrile (CHEBI:18379)
Incoming cimetidine S-oxide (CHEBI:30731) has functional parent cimetidine (CHEBI:3699)
cimetidine hydrochloride (CHEBI:50362) has part cimetidine (CHEBI:3699)
IUPAC Name
2-cyano-1-methyl-3-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine
INNs Sources
cimetidina ChemIDplus
cimetidine ChemIDplus
cimétidine ChEBI
cimetidinum ChemIDplus
Synonyms Sources
1-Cyano-2-methyl-3-(2-(((5-methyl-4-imidazolyl)methyl)thio)ethyl)guanidine ChemIDplus
2-cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)guanidine NIST Chemistry WebBook
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 NIST Chemistry WebBook
Brand Names Sources
Cimetag DrugBank
Tagamet HB 200 DrugBank
Ulcerfen DrugBank
Manual Xrefs Databases
1892 VSDB
645 DrugCentral
BE804144 Patent
Cimetidine Wikipedia
D00295 KEGG DRUG
DB00501 DrugBank
HMDB0014644 HMDB
LSM-2404 LINCS
US3950333 Patent
View more database links
Registry Numbers Types Sources
51481-61-9 CAS Registry Number NIST Chemistry WebBook
51481-61-9 CAS Registry Number ChemIDplus
6516325 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11910267 PubMed citation Europe PMC
15637527 PubMed citation Europe PMC
7229121 PubMed citation Europe PMC
Last Modified
22 February 2017