U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C18H26ClN3O3.ClH
Molecular Weight 404.331
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRUCALOPRIDE HYDROCHLORIDE

SMILES

Cl.COCCCN1CCC(CC1)NC(=O)C2=CC(Cl)=C(N)C3=C2OCC3

InChI

InChIKey=KKMOQGWTJRGLNN-UHFFFAOYSA-N
InChI=1S/C18H26ClN3O3.ClH/c1-24-9-2-6-22-7-3-12(4-8-22)21-18(23)14-11-15(19)16(20)13-5-10-25-17(13)14;/h11-12H,2-10,20H2,1H3,(H,21,23);1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H26ClN3O3
Molecular Weight 367.87
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Prucalopride is a novel enterokinetic compound and is the first representative of the benzofuran class. Prucalopride is a potent, selective and specific serotonin 5-HT4 receptor (5-HT4-R) agonist. Prucalopride (Resolor®), a highly selective serotonin 5-HT4 receptor agonist, is indicated in the European Economic Area for the treatment of adults with chronic idiopathic constipation (CIC) in whom laxatives have failed to provide adequate relief.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.6 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RESOLOR
PubMed

PubMed

TitleDatePubMed
Structure of the human serotonin 5-HT4 receptor gene and cloning of a novel 5-HT4 splice variant.
2000 Feb
Serotonin: a mediator of the brain-gut connection.
2000 Oct
Irritable bowel syndrome: new agents targeting serotonin receptor subtypes.
2001
5-HT(4) receptors mediating enhancement of contractility in canine stomach; an in vitro and in vivo study.
2001 Apr
Gastrointestinal prokinetic drugs have different affinity for the human cardiac human ether-à-gogo K(+) channel.
2001 Dec
Prucalopride accelerates gastrointestinal and colonic transit in patients with constipation without a rectal evacuation disorder.
2001 Feb
Drug therapy options for patients with irritable bowel syndrome.
2001 Jul
The in vitro pharmacological profile of prucalopride, a novel enterokinetic compound.
2001 Jun 29
Characterization of the receptors involved in the 5-HT-induced excitation of canine antral longitudinal muscle.
2001 Nov
The human serotonin 5-HT4 receptor regulates secretion of non-amyloidogenic precursor protein.
2001 Nov 30
Central serotonin4 receptors selectively regulate the impulse-dependent exocytosis of dopamine in the rat striatum: in vivo studies with morphine, amphetamine and cocaine.
2002 Dec
Emerging treatments for irritable bowel syndrome.
2002 Jan
Irritable bowel syndrome: update on pathogenesis and management.
2002 Jan-Mar
New and emerging treatments for irritable bowel syndrome and functional dyspepsia.
2002 May
5-HT4 receptors exert a frequency-related facilitatory control on dorsal raphé nucleus 5-HT neuronal activity.
2002 Sep
The serotonin 5-HT4 receptor and the amyloid precursor protein processing.
2003 Jan-Feb
Gateways to clinical trials.
2003 Oct
Gastrointestinal motility disorders and gastrointestinal prokinetic therapy.
2003 Sep
The treatment of chronic constipation in elderly people: an update.
2004
Presynaptic modulation of cholinergic and non-cholinergic fast synaptic transmission in the myenteric plexus of guinea pig ileum.
2004 Jun
Frontocortical 5-HT4 receptors exert positive feedback on serotonergic activity: viral transfections, subacute and chronic treatments with 5-HT4 agonists.
2005 Apr 15
Fading of 5-HT4 receptor-mediated inotropic responses to 5-hydroxytryptamine is caused by phosphodiesterase activity in porcine atrium.
2006 Jan
Differential effects of 5-hydroxytryptamine4 receptor agonists at gastric versus cardiac receptors: an operational framework to explain and quantify organ-specific behavior.
2006 Jun
5-HT4 receptor agonists increase sAPPalpha levels in the cortex and hippocampus of male C57BL/6j mice.
2007 Apr
The serotonin signaling system: from basic understanding to drug development for functional GI disorders.
2007 Jan
Electrophysiological and arrhythmogenic effects of 5-hydroxytryptamine on human atrial cells are reduced in atrial fibrillation.
2007 Jan
5-HT4 receptor agonists: similar but not the same.
2008 Feb
Gastric and enteric involvement in progressive systemic sclerosis.
2008 Jan
A placebo-controlled trial of prucalopride for severe chronic constipation.
2008 May 29
Gateways to clinical trials.
2008 Sep
Safety assessment of prucalopride in elderly patients with constipation: a double-blind, placebo-controlled study.
2009 Dec
Motility: prucalopride for chronic constipation.
2009 Jun
Gateways to clinical trials.
2009 Mar
The use of novel promotility and prosecretory agents for the treatment of chronic idiopathic constipation and irritable bowel syndrome with constipation.
2009 May
Update on the management of constipation in the elderly: new treatment options.
2010 Aug 9
Psychometric performance and clinical meaningfulness of the Patient Assessment of Constipation-Quality of Life questionnaire in prucalopride (RESOLOR) trials for chronic constipation.
2010 Feb
Selective serotonin reuptake inhibitors potentiate the rapid antidepressant-like effects of serotonin4 receptor agonists in the rat.
2010 Feb 16
New-generation 5-HT4 receptor agonists: potential for treatment of gastrointestinal motility disorders.
2010 Jun
Fixed combination of oxycodone with naloxone: a new way to prevent and treat opioid-induced constipation.
2010 Sep
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Adults: 2 mg once daily with or without food, at any time of the day.
Route of Administration: Oral
In Vitro Use Guide
Cell shortening and real-time Ca(2+) measurements were processed on field-stimulated intact cardiomyocytes with the selective 5-HT4R agonist, prucalopride (1 uM).
Substance Class Chemical
Created
by admin
on Tue Oct 22 13:38:57 UTC 2019
Edited
by admin
on Tue Oct 22 13:38:57 UTC 2019
Record UNII
M8IYX9Z79V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRUCALOPRIDE HYDROCHLORIDE
MART.   WHO-DD  
Common Name English
4-AMINO-5-CHLORO-2,3-DIHYDRO-N-(1-(3-METHOXYPROPYL)-4-PIPERIDINYL)-7-BENZOFURANCARBOXAMIDE HYDROCHLORIDE
Systematic Name English
PRUCALOPRIDE HYDROCHLORIDE [MART.]
Common Name English
PRUCALOPRIDE HYDROCHLORIDE [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
9931054
Created by admin on Tue Oct 22 13:38:57 UTC 2019 , Edited by admin on Tue Oct 22 13:38:57 UTC 2019
PRIMARY
EVMPD
SUB79171
Created by admin on Tue Oct 22 13:38:57 UTC 2019 , Edited by admin on Tue Oct 22 13:38:57 UTC 2019
PRIMARY
CAS
179474-80-7
Created by admin on Tue Oct 22 13:38:57 UTC 2019 , Edited by admin on Tue Oct 22 13:38:57 UTC 2019
PRIMARY
EPA CompTox
179474-80-7
Created by admin on Tue Oct 22 13:38:57 UTC 2019 , Edited by admin on Tue Oct 22 13:38:57 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY