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Details

Stereochemistry ACHIRAL
Molecular Formula C18H26ClN3O3
Molecular Weight 367.87
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRUCALOPRIDE

SMILES

COCCCN1CCC(CC1)NC(=O)C2=C3OCCC3=C(N)C(Cl)=C2

InChI

InChIKey=ZPMNHBXQOOVQJL-UHFFFAOYSA-N
InChI=1S/C18H26ClN3O3/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)

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

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
Pharmacological treatment of irritable bowel syndrome--from concept to sales.
2002
New and emerging treatments for irritable bowel syndrome and functional dyspepsia.
2002 May
The treatment of chronic constipation in elderly people: an update.
2004
Modulation of hippocampal excitability by 5-HT4 receptor agonists persists in a transgenic model of Alzheimer's disease.
2004
Electrophysiological effects of prucalopride, a novel enterokinetic agent, on isolated atrial myocytes from patients treated with beta-adrenoceptor antagonists.
2005 Apr
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
Prucalopride is a partial agonist through human and porcine atrial 5-HT4 receptors: comparison with recombinant human 5-HT4 splice variants.
2005 Jun
5-HT4 receptors located on cholinergic nerves in human colon circular muscle.
2005 Jun
Management of faecal incontinence and constipation in adults with central neurological diseases.
2006 Apr 19
Increased cholinergic contractions of jejunal smooth muscle caused by a high cholesterol diet are prevented by the 5-HT4 agonist--tegaserod.
2006 Feb 23
Porcine left atrial and sinoatrial 5-HT(4) receptor-induced responses: fading of the response and influence of development.
2006 Jan
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
Investigation of serotonin receptors in the isolated penile bulb of rats.
2006 Nov-Dec
5HT4 agonists inhibit interferon-gamma-induced MHC class II and B7 costimulatory molecules expression on cultured astrocytes.
2006 Oct
5-HT4 receptor agonists enhance both cholinergic and nitrergic activities in human isolated colon circular muscle.
2006 Sep
5-HT4 receptor agonists increase sAPPalpha levels in the cortex and hippocampus of male C57BL/6j mice.
2007 Apr
Recent advances in understanding the role of serotonin in gastrointestinal motility in functional bowel disorders: alterations in 5-HT signalling and metabolism in human disease.
2007 Aug
The serotonin signaling system: from basic understanding to drug development for functional GI disorders.
2007 Jan
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
The action of the novel gastrointestinal prokinetic prucalopride on the HERG K+ channel and the common T897 polymorph.
2007 Jan 12
5-HT4 receptor agonists: similar but not the same.
2008 Feb
Gastric and enteric involvement in progressive systemic sclerosis.
2008 Jan
Gateways to clinical trials. July-August 2008.
2008 Jul-Aug
Prucalopride: the evidence for its use in the treatment of chronic constipation.
2008 Jun
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
Synergy between 5-HT4 receptor activation and acetylcholinesterase inhibition in human colon and rat forestomach.
2008 May
The long and short of a constipation-reducing medication.
2008 May 29
A placebo-controlled trial of prucalopride for severe chronic constipation.
2008 May 29
New treatments for irritable bowel syndrome in women.
2008 Nov
[Functional and motor gastrointestinal disorders].
2008 Oct
Gateways to clinical trials.
2008 Oct
Gateways to clinical trials.
2008 Sep
Management of constipation in the elderly: emerging therapeutic strategies.
2008 Sep 7
Gateways to clinical trials.
2009 Apr
Translating 5-HT receptor pharmacology.
2009 Dec
Safety assessment of prucalopride in elderly patients with constipation: a double-blind, placebo-controlled study.
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
Motility: prucalopride for chronic constipation.
2009 Jun
Gateways to clinical trials.
2009 Mar
Comments on tegaserod trial on irritable bowel syndrome.
2010 Apr
Update on the management of constipation in the elderly: new treatment options.
2010 Aug 9
[New drugs for the treatment of constipation].
2010 Jul
Influence of 5-HT4 receptor activation on acetylcholine release in human large intestine with endometriosis.
2010 May
Emerging pharmacologic therapies for irritable bowel syndrome.
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 01:43:01 UTC 2019
Edited
by admin
on Tue Oct 22 01:43:01 UTC 2019
Record UNII
0A09IUW5TP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRUCALOPRIDE
EMA EPAR   INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
R-093877
Code English
PRUCALOPRIDE [EMA EPAR]
Common Name English
PRUCALOPRIDE [MI]
Common Name English
R093877
Common Name English
PRUCALOPRIDE [USAN]
Common Name English
PRUCALOPRIDE [WHO-DD]
Common Name English
PRUCALOPRIDE [MART.]
Common Name English
PRUCALOPRIDE [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC A03AE04
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
NCI_THESAURUS C47794
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
WHO-ATC A06AX05
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
WHO-VATC QA06AX05
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
Code System Code Type Description
INN
7702
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
PRIMARY
EVMPD
SUB10155MIG
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
PRIMARY
NCI_THESAURUS
C74386
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
PRIMARY
MESH
C406662
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
PRIMARY
EPA CompTox
179474-81-8
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
PRIMARY
ChEMBL
CHEMBL117287
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
PRIMARY
IUPHAR
243
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
PRIMARY
DRUG BANK
DB06480
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
PRIMARY
WIKIPEDIA
PRUCALOPRIDE
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
PRIMARY
MERCK INDEX
M9285
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
PRIMARY Merck Index
CAS
179474-81-8
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
PRIMARY
PUBCHEM
3052762
Created by admin on Tue Oct 22 01:43:01 UTC 2019 , Edited by admin on Tue Oct 22 01:43:01 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
EXCRETED UNCHANGED
URINE
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Interaction with the 5-HT4 receptor leads to the elevation of cyclic adenosine monophosphate (cAMP) levels in HEK293 cells
EC50
BINDER->LIGAND
In human plasma, the binding of R093877 increased at higher pH values. In the pH-range 7.1 to 7.7, the percentage bound increased from 23.3% to 35.5%
BINDING
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
Seven metabolites were recovered in urine and feces, with the most abundant metabolite R107504 (O-desmethyl prucalopride acid) accounting for 3.2% and 3.1% of the dose in urine and feces, respectively.
FECAL; URINE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC ROUTE OF ADMINISTRATION
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC DOSE
PHARMACOKINETIC
ROUTE OF ADMINISTRATION
PHARMACOKINETIC