Bromopride

Identification

Summary

Bromopride is a substituted benzamide, closely related to metoclopramide, used as an antiemetic.

Generic Name
Bromopride
DrugBank Accession Number
DB09018
Background

Bromopride is a dopamine antagonist used as an antiemetic. Its prokinetic properties are similar to those of metoclopramide. It is unavailable in America or the United Kingdom.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 344.247
Monoisotopic: 343.08953961
Chemical Formula
C14H22BrN3O2
Synonyms
  • 4-amino-5-bromo-N-[2-(diethylamino)ethyl]-2-methoxybenzamide
  • Bromoprid
  • Bromoprida
  • Bromopride
  • Bromopridum
External IDs
  • VAL 13081

Pharmacology

Indication

Bromopride in indicated in the treatment of nausea and vomiting, including PONV (post-operative nausea and vomiting), gastroesophageal reflux disease (GERD/GORD), as well as endoscopy preparation and radiographic studies of the GI tract.

Pharmacology
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Drug Discovery
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ADopamine D2 receptor
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

40%.

Metabolism

Hepatic.

Route of elimination

Not Available

Half-life

Not Available

Clearance

Renal, 10-14% as original compound.

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
ApomorphineThe therapeutic efficacy of Apomorphine can be decreased when used in combination with Bromopride.
AripiprazoleThe therapeutic efficacy of Aripiprazole can be decreased when used in combination with Bromopride.
BenzatropineThe risk or severity of adverse effects can be increased when Bromopride is combined with Benzatropine.
BrexpiprazoleThe therapeutic efficacy of Brexpiprazole can be decreased when used in combination with Bromopride.
BromocriptineThe therapeutic efficacy of Bromocriptine can be decreased when used in combination with Bromopride.
CabergolineThe therapeutic efficacy of Cabergoline can be decreased when used in combination with Bromopride.
DeutetrabenazineThe risk or severity of adverse effects can be increased when Bromopride is combined with Deutetrabenazine.
DihydroergocornineThe therapeutic efficacy of Dihydroergocornine can be decreased when used in combination with Bromopride.
DihydroergotamineThe therapeutic efficacy of Dihydroergotamine can be decreased when used in combination with Bromopride.
DopexamineThe therapeutic efficacy of Dopexamine can be decreased when used in combination with Bromopride.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Bromopan (UCI) / Digesan (Sanofi) / Emepride / Emoril / Movipride (Merck) / Plamet / Viadil

Categories

ATC Codes
A03FA04 — Bromopride
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminophenyl ethers. These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Aminophenyl ethers
Direct Parent
Aminophenyl ethers
Alternative Parents
Methoxyanilines / Phenoxy compounds / Methoxybenzenes / Anisoles / 2-bromoanilines / Bromobenzenes / Alkyl aryl ethers / Aryl bromides / Trialkylamines / Propargyl-type 1,3-dipolar organic compounds
show 5 more
Substituents
2-bromoaniline / Alkyl aryl ether / Amine / Aminophenyl ether / Aniline or substituted anilines / Anisole / Aromatic homomonocyclic compound / Aryl bromide / Aryl halide / Bromobenzene
show 21 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
75473V2YZK
CAS number
4093-35-0
InChI Key
GIYAQDDTCWHPPL-UHFFFAOYSA-N
InChI
InChI=1S/C14H22BrN3O2/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)
IUPAC Name
4-amino-5-bromo-N-[2-(diethylamino)ethyl]-2-methoxybenzamide
SMILES
CCN(CC)CCNC(=O)C1=CC(Br)=C(N)C=C1OC

References

Synthesis Reference

U.S. Patents 3,177,252; 3,219,528; and 3,357,978.

General References
Not Available
KEGG Drug
D07101
PubChem Compound
2446
PubChem Substance
310264975
ChemSpider
2352
BindingDB
50247887
RxNav
19768
ChEBI
95304
ChEMBL
CHEMBL399510
ZINC
ZINC000002038104
Drugs.com
Drugs.com Drug Page
Wikipedia
Bromopride
MSDS
Download (105 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentDyspepsia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOral4 mg
SolutionOral1 mg
Tablet, coatedOral
TabletOral
Pill
Tablet, coated
Capsule
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US3177252No1962-07-171982-07-17US flag
US3219528No1962-07-171982-07-17US flag
US3357978No1964-02-281984-02-28US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)134-135U.S. Patents 3,177,252; 3,219,528; and 3,357,978.
Predicted Properties
PropertyValueSource
Water Solubility0.241 mg/mLALOGPS
logP2.36ALOGPS
logP1.56ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)9.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.59 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity86.34 m3·mol-1ChemAxon
Polarizability33.92 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00b9-2490000000-42a1d3cd086a6021ec5b

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Tonini M, Cipollina L, Poluzzi E, Crema F, Corazza GR, De Ponti F: Review article: clinical implications of enteric and central D2 receptor blockade by antidopaminergic gastrointestinal prokinetics. Aliment Pharmacol Ther. 2004 Feb 15;19(4):379-90. [Article]

Drug created on June 23, 2014 21:53 / Updated on May 27, 2021 02:57