CHEBI:107736 - metoclopramide

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ChEBI Name metoclopramide
ChEBI ID CHEBI:107736
Definition A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of N,N-diethylethane-1,2-diamine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6898
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Formula C14H22ClN3O2
Net Charge 0
Average Mass 299.79600
Monoisotopic Mass 299.140
InChI InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)
InChIKey TTWJBBZEZQICBI-UHFFFAOYSA-N
SMILES CCN(CC)CCNC(=O)c1cc(Cl)c(N)cc1OC
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): antiemetic
A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.
dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
gastrointestinal drug
A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.
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ChEBI Ontology
Outgoing metoclopramide (CHEBI:107736) has role antiemetic (CHEBI:50919)
metoclopramide (CHEBI:107736) has role dopaminergic antagonist (CHEBI:48561)
metoclopramide (CHEBI:107736) has role environmental contaminant (CHEBI:78298)
metoclopramide (CHEBI:107736) has role gastrointestinal drug (CHEBI:55324)
metoclopramide (CHEBI:107736) has role xenobiotic (CHEBI:35703)
metoclopramide (CHEBI:107736) is a benzamides (CHEBI:22702)
metoclopramide (CHEBI:107736) is a monochlorobenzenes (CHEBI:83403)
metoclopramide (CHEBI:107736) is a substituted aniline (CHEBI:48975)
metoclopramide (CHEBI:107736) is a tertiary amino compound (CHEBI:50996)
metoclopramide (CHEBI:107736) is conjugate base of metoclopramide(1+) (CHEBI:61170)
Incoming metoclopramide(1+) (CHEBI:61170) is conjugate acid of metoclopramide (CHEBI:107736)
IUPAC Name
4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide
INNs Sources
metoclopramida ChemIDplus
metoclopramide ChemIDplus
metoclopramidum ChemIDplus
Synonyms Sources
2-methoxy-4-amino-5-chloro-N,N-(dimethylaminoethyl)benzamide ChemIDplus
2-methoxy-5-chloroprocainamide ChemIDplus
4-amino-5-chloro-2-methoxy-N-(β-diethylaminoethyl)benzamide ChemIDplus
4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide ChEMBL
4-amino-5-chloro-N-(2-(diethylamino)ethyl)-o-anisamide ChemIDplus
Brand Names Sources
Elieten DrugBank
Reliveran DrugBank
Database Links Databases
1782 DrugCentral
BE620543 Patent
C07868 KEGG COMPOUND
D00726 KEGG DRUG
DB01233 DrugBank
HMDB15363 HMDB
LSM-3689 LINCS
Metoclopramide Wikipedia
US3177252 Patent
View more database links
Registry Numbers Types Sources
1884366 Reaxys Registry Number Reaxys
364-62-5 CAS Registry Number ChemIDplus
364-62-5 CAS Registry Number KEGG DRUG
Last Modified
22 February 2017
General Comments
2011-01-12 Metoclopramide is a dopamine D2 antagonist. It is used (particularly as the monohydrochloride monohydrate, commonly known as metoclopramide hydrochloride) to increase motility of the upper gastrointestinal tract in disorders such as gastro-oesophageal reflux, and for the treatment of nausea and vomiting associated with various gastrointestinal disorders, with migraine, following surgery, and with cancer therapy. Although chemically related to procainamide, metoclopramide does not possess local anaesthetic or anti-arrhythmic properties.
2014-07-16 Metoclopramide can be found in blood and urine samples of individuals who have taken this drug.