Identification

Name
Bromopride
Accession Number
DB09018
Type
Small Molecule
Groups
Approved, Investigational
Description

Bromopride is a dopamine antagonist with prokinetic properties closely related to metoclopramide, and is widely used as an antiemetic. It is not available in the United States or the United Kingdom.

Structure
Thumb
Synonyms
  • 4-amino-5-bromo-N-[2-(diethylamino)ethyl]-2-methoxybenzamide
  • Bromoprid
  • Bromoprida
  • Bromopride
  • Bromopridum
External IDs
VAL 13081
International/Other Brands
Bromopan (UCI) / Digesan (Sanofi) / Movipride (Merck)
Categories
UNII
75473V2YZK
CAS number
4093-35-0
Weight
Average: 344.247
Monoisotopic: 343.08953961
Chemical Formula
C14H22BrN3O2
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-methoxybenzene-1-carboximidic acid
SMILES
CCN(CC)CCN=C(O)C1=C(OC)C=C(N)C(Br)=C1

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.

Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
AD(2) dopamine receptor
antagonist
Human
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.

Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
SulpirideThe risk or severity of adverse effects can be increased when Bromopride is combined with Sulpiride.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

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

General References
Not Available
External Links
KEGG Drug
D07101
PubChem Compound
2446
PubChem Substance
310264975
ChemSpider
2352
ChEBI
95304
ChEMBL
CHEMBL399510
Drugs.com
Drugs.com Drug Page
Wikipedia
Bromopride
ATC Codes
A03FA04 — Bromopride
MSDS
Download (105 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3RecruitingTreatmentIndigestion1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US3177252No1962-07-171982-07-17Us
US3219528No1962-07-171982-07-17Us
US3357978No1964-02-281984-02-28Us

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 Solubility0.133 mg/mLALOGPS
logP2.48ALOGPS
logP0.79ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)7.55ChemAxon
pKa (Strongest Basic)9.56ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area71.08 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity86.86 m3·mol-1ChemAxon
Polarizability34.09 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

Taxonomy

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
Aminophenyl ether / Methoxyaniline / Anisole / Phenoxy compound / 2-bromoaniline / Aniline or substituted anilines / Methoxybenzene / Alkyl aryl ether / Bromobenzene / Halobenzene
show 21 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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. [PubMed:14871277]

Drug created on June 23, 2014 15:53 / Updated on December 01, 2017 16:12