GtoPdb Ligand ID: 241

Synonyms: metaclopromide | methochlopramide | metochlopramide | metoclopramide hydrochloride | Reglan®
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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2D Structure
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Physico-chemical Properties
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
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)
No information available.
Summary of Clinical Use
Used as an antiemetic, in the treatment of gastroesophageal reflux disease and to increase gastric emptying.
Mechanism Of Action and Pharmacodynamic Effects
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.