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Details

Stereochemistry ACHIRAL
Molecular Formula C18H26ClN3O3.C4H6O4
Molecular Weight 485.958
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRUCALOPRIDE SUCCINATE

SMILES

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

InChI

InChIKey=QZRSNVSQLGRAID-UHFFFAOYSA-N
InChI=1S/C18H26ClN3O3.C4H6O4/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;5-3(6)1-2-4(7)8/h11-12H,2-10,20H2,1H3,(H,21,23);1-2H2,(H,5,6)(H,7,8)

HIDE SMILES / InChI

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

Molecular Formula C4H6O4
Molecular Weight 118.088
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
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
Prucalopride accelerates gastrointestinal and colonic transit in patients with constipation without a rectal evacuation disorder.
2001 Feb
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
Effects of the enterokinetic prucalopride (R093877) on colonic motility in fasted dogs.
2001 Oct
Presynaptic modulation of cholinergic neurotransmission in the human proximal stomach.
2002 Jan
Emerging treatments for irritable bowel syndrome.
2002 Jan
Differences in signal transduction of two 5-HT4 receptor splice variants: compound specificity and dual coupling with Galphas- and Galphai/o-proteins.
2002 Jan
Prucalopride, a systemic enterokinetic, for the treatment of constipation.
2002 Jul
Review article: the complexity of drug development for irritable bowel syndrome.
2002 Mar
New and emerging treatments for irritable bowel syndrome and functional dyspepsia.
2002 May
Prucalopride is effective in patients with severe chronic constipation in whom laxatives fail to provide adequate relief. Results of a double-blind, placebo-controlled clinical trial.
2003
Irritable bowel syndrome: an overview of diagnosis and pharmacologic treatment.
2003 Jun
Gateways to clinical trials.
2003 May
Gastrointestinal motility disorders and gastrointestinal prokinetic therapy.
2003 Sep
Modulation of hippocampal excitability by 5-HT4 receptor agonists persists in a transgenic model of Alzheimer's disease.
2004
Rationale for using serotonergic agents to treat irritable bowel syndrome.
2005 Apr 1
Frontocortical 5-HT4 receptors exert positive feedback on serotonergic activity: viral transfections, subacute and chronic treatments with 5-HT4 agonists.
2005 Apr 15
5-HT4 receptors located on cholinergic nerves in human colon circular muscle.
2005 Jun
Increased cholinergic contractions of jejunal smooth muscle caused by a high cholesterol diet are prevented by the 5-HT4 agonist--tegaserod.
2006 Feb 23
Little or no ability of obestatin to interact with ghrelin or modify motility in the rat gastrointestinal tract.
2007 Jan
Electrophysiological and arrhythmogenic effects of 5-hydroxytryptamine on human atrial cells are reduced in atrial fibrillation.
2007 Jan
Gateways to clinical trials. July-August 2008.
2008 Jul-Aug
Alternative splicing and exon duplication generates 10 unique porcine 5-HT 4 receptor splice variants including a functional homofusion variant.
2008 Jun 12
Prucalopride and donepezil act synergistically to reverse scopolamine-induced memory deficit in C57Bl/6j mice.
2008 Mar 5
A placebo-controlled trial of prucalopride for severe chronic constipation.
2008 May 29
Gateways to clinical trials.
2008 Oct
Prucalopride.
2009
Prucalopride: a new drug for the treatment of chronic constipation.
2009 Aug
Prucalopride for chronic constipation.
2009 Dec
Clinical trial: the efficacy, impact on quality of life, and safety and tolerability of prucalopride in severe chronic constipation--a 12-week, randomized, double-blind, placebo-controlled study.
2009 Feb 1
Selective desensitization of the 5-HT4 receptor-mediated response in pig atrium but not in stomach.
2009 Jan
New-generation 5-HT4 receptor agonists: potential for treatment of gastrointestinal motility disorders.
2010 Jun
Hyperfunction of muscarinic receptor maintains long-term memory in 5-HT4 receptor knock-out mice.
2010 Mar 4
Emerging pharmacologic therapies for irritable bowel syndrome.
2010 Oct
Efficacy and safety of prucalopride in patients with chronic noncancer pain suffering from opioid-induced constipation.
2010 Oct
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 01:43:08 UTC 2019
Edited
by admin
on Tue Oct 22 01:43:08 UTC 2019
Record UNII
4V2G75E1CK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRUCALOPRIDE SUCCINATE
MART.   USAN   WHO-DD  
USAN  
Official Name English
PRUCALOPRIDE SUCCINATE [USAN]
Common Name English
PRUCALOPRIDE SUCCINATE [MART.]
Common Name English
MOTEGRITY
Brand Name English
PRUCALOPRIDE (AS SUCCINATE)
Common Name English
PRUCALOPRIDE SUCCINATE [WHO-DD]
Common Name English
BUTANEDIOIC ACID, COMPD. WITH 4-AMINO-5-CHLORO-2,3-DIHYDRO-N-(1-(3-METHOXYPROPYL)-4-PIPERIDINYL)-7-BENZOFURANCARBOXAMIDE (1:1)
Common Name English
RESOLOR
Brand Name English
R-108512
Code English
Classification Tree Code System Code
NCI_THESAURUS C47794
Created by admin on Tue Oct 22 01:43:08 UTC 2019 , Edited by admin on Tue Oct 22 01:43:08 UTC 2019
EMA ASSESSMENT REPORTS RESOLOR (AUTHORIZED: CONSTIPATION)
Created by admin on Tue Oct 22 01:43:08 UTC 2019 , Edited by admin on Tue Oct 22 01:43:08 UTC 2019
Code System Code Type Description
PUBCHEM
9870009
Created by admin on Tue Oct 22 01:43:08 UTC 2019 , Edited by admin on Tue Oct 22 01:43:08 UTC 2019
PRIMARY
EVMPD
SUB28850
Created by admin on Tue Oct 22 01:43:08 UTC 2019 , Edited by admin on Tue Oct 22 01:43:08 UTC 2019
PRIMARY
NCI_THESAURUS
C152112
Created by admin on Tue Oct 22 01:43:08 UTC 2019 , Edited by admin on Tue Oct 22 01:43:08 UTC 2019
PRIMARY
CAS
179474-85-2
Created by admin on Tue Oct 22 01:43:08 UTC 2019 , Edited by admin on Tue Oct 22 01:43:08 UTC 2019
PRIMARY
ChEMBL
CHEMBL117287
Created by admin on Tue Oct 22 01:43:08 UTC 2019 , Edited by admin on Tue Oct 22 01:43:08 UTC 2019
PRIMARY
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