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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
Prucalopride: the evidence for its use in the treatment of chronic constipation.
2008 Jun
Gateways to clinical trials.
2008 Sep
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
New-generation 5-HT4 receptor agonists: potential for treatment of gastrointestinal motility disorders.
2010 Jun
Psychometric evaluation of a visual analog scale for the assessment of anxiety.
2010 Jun 8
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
A double-blind, placebo-controlled study of prucalopride in elderly patients with chronic 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