CHEBI:60906 - metoclopramide dihydrochloride monohydrate

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ChEBI Name metoclopramide dihydrochloride monohydrate
ChEBI ID CHEBI:60906
Definition A hydrate that is the monohydrate form of metoclopramide dihydrochloride.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C14H26Cl3N3O3
Net Charge 0
Average Mass 390.73400
Monoisotopic Mass 389.10397
InChI InChI=1S/C14H22ClN3O2.2ClH.H2O/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);2*1H;1H2
InChIKey IRQVJPHZDYMXNW-UHFFFAOYSA-N
SMILES O.[Cl-].[Cl-].CC[NH+](CC)CCNC(=O)c1cc(Cl)c([NH3+])cc1OC
Roles Classification
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.
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 dihydrochloride monohydrate (CHEBI:60906) has part metoclopramide hydrochloride (CHEBI:6899)
metoclopramide dihydrochloride monohydrate (CHEBI:60906) has part metoclopramide(2+) (CHEBI:61172)
metoclopramide dihydrochloride monohydrate (CHEBI:60906) has role antiemetic (CHEBI:50919)
metoclopramide dihydrochloride monohydrate (CHEBI:60906) has role dopaminergic antagonist (CHEBI:48561)
metoclopramide dihydrochloride monohydrate (CHEBI:60906) has role gastrointestinal drug (CHEBI:55324)
metoclopramide dihydrochloride monohydrate (CHEBI:60906) is a hydrate (CHEBI:35505)
metoclopramide dihydrochloride monohydrate (CHEBI:60906) is a hydrochloride (CHEBI:36807)
IUPAC Names
2-chloro-4-{[2-(diethylammonio)ethyl]carbamoyl}-5-methoxyanilinium dichloride—water (1/1)
4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide dihydrochloride—water (1/1)
Synonyms Sources
2-methoxy-4-amino-5-chloro-N-(β-(diethylamino)ethyl)benzamide dihydrochloride monohydrate ChemIDplus
4-amino-5-chloro-N-(2-(diethylamino)ethyl)-o-anisamide dihydrochloride monohydrate ChemIDplus
Brand Names Sources
Emetid DrugBank
Gastronerton DrugBank
Primperan DrugBank
Manual Xrefs Databases
D02213 KEGG DRUG
DB01233 DrugBank
View more database links
Registry Numbers Types Sources
5581-45-3 CAS Registry Number ChemIDplus
5581-45-3 CAS Registry Number KEGG DRUG
6672858 Reaxys Registry Number Reaxys
Last Modified
02 February 2011
General Comment
2011-01-12 Metoclopramide is a dopamine D2 antagonist. It is used (particularly as the monohydrochloride monohydrate, commonly known as metoclopramide hydrochloride, but also as the dihydrochloride monohydrate) 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.