metoclopramide   Click here for help

GtoPdb Ligand ID: 241

Synonyms: Gimoti® (metoclopramide nasal spray) | metaclopromide | methochlopramide | metochlopramide | metoclopramide hydrochloride | Reglan®
Approved drug
metoclopramide is an approved drug (FDA (1979))
Compound class: Synthetic organic
Comment: Metoclopramide is a promarily dopamine receptor antagonist, but it also exhibits mixed 5-HT3 receptor antagonist/5-HT4 receptor agonist activity.
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View more information in the IUPHAR Pharmacology Education Project: metoclopramide

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 67.59
Molecular weight 299.14
XLogP 1.85
No. Lipinski's rules broken 0
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Canonical SMILES CCN(CCNC(=O)c1cc(Cl)c(cc1OC)N)CC
Isomeric SMILES CCN(CCNC(=O)c1cc(Cl)c(cc1OC)N)CC
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)
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Summary of Clinical Use Click here for help
Used as an antiemetic, in the treatment of gastroesophageal reflux disease and to increase gastric emptying. In June 2020, the FDA approved marketing of metoclopramide nasal spray for the relief of symptoms of acute and recurrent diabetic gastroparesis.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Antagonist activity at D2 receptors in the chemoreceptor trigger zone of the brain underlies metoclopramide's antiemetic action. 5-HT4 receptor agonist activity and muscarinic activity may also provide additive beneficial antiemetic/gastroprokinetic effects.