domperidone   Click here for help

GtoPdb Ligand ID: 965

Synonyms: Motilium® | Nauzelin® | R-33812
Approved drug
domperidone is an approved drug
Compound class: Synthetic organic
Comment: Domperidone is an orally active, peripherally acting and selective antagonist of dopamine D2 and D3 receptors.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: domperidone

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 78.82
Molecular weight 425.16
XLogP 2.37
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES Clc1ccc2c(c1)[nH]c(=O)n2C1CCN(CC1)CCCn1c(=O)[nH]c2c1cccc2
Isomeric SMILES Clc1ccc2c(c1)[nH]c(=O)n2C1CCN(CC1)CCCn1c(=O)[nH]c2c1cccc2
InChI InChI=1S/C22H24ClN5O2/c23-15-6-7-20-18(14-15)25-22(30)28(20)16-8-12-26(13-9-16)10-3-11-27-19-5-2-1-4-17(19)24-21(27)29/h1-2,4-7,14,16H,3,8-13H2,(H,24,29)(H,25,30)
InChI Key FGXWKSZFVQUSTL-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Domperidone is used to manage dyspepsia, heartburn, epigastric pain, nausea, and vomiting. In some countries, domperidone is self-prescribed or prescribed for off-label use to enhance lactation. Domperidone-containing medicines are widely available over-the-counter or prescription-only medicines. Neither the US FDA or European Medicines Agency (EMA) websites carry information regarding marketing approval for domperidone, although both note that approval is granted by individual national agencies. The EMA is reviewing the benefit-risk balance of domperidone-containing medicines (March 2013)
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Domperidone blocks dopamine receptors in the gut and in the part of the brain linked to vomiting (the chemoreceptor trigger zone, located just outside the blood brain barrier). This results in increased esophageal and gastric peristalsis, such that food moves more quickly through the stomach and into the intestine. This helps prevent vomiting and reduces feelings of sickness, bloating and fullness. Domperidone also stimulates prolactin release.