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SML1371

Sigma-Aldrich

Prucalopride

≥98% (HPLC)

Synonym(s):

4-Amino-5-chloro-2,3-dihydro-N-[1-(3-methoxypropyl)-4-piperidinyl]-7-benzofurancarboxamide

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About This Item

Empirical Formula (Hill Notation):
C18H26ClN3O3
CAS Number:
179474-81-8
Molecular Weight:
367.87
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

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

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)

InChI key

ZPMNHBXQOOVQJL-UHFFFAOYSA-N

Biochem/physiol Actions

In healthy male individuals, prucalopride decreases the display of esophageal acid and promotes gastric emptying. It is effective, safe and shows good tolerance for the treatment of men with chronic constipation.
Prucalopride is a selective 5-HT4 serotonin receptor agonist with enterokinetic activity. 5-HT4 receptors are GPCRs that are expressed in the CNS and peripheral tissues. The receptor has a role in GI motility disorders such as irritable bowel syndrome and idiopathic constipation. Agonists are prokinetic and of potential use for disoroders of reduced motility. Prucalopride is a selective 5-HT4 serotonin receptor agonist with enterokinetic activities. Prucalopride has pK(i) values of 8.60 and 8.10 for the human 5-HT(4a) and 5-HT(4b) receptor, respectively, and at least 290-fold selectivity for 5-HT4 over other serotonin and dopamine receptors.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Aquatic Acute 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Prucalopride decreases esophageal acid exposure and accelerates gastric emptying in healthy subjects.
Kessing BF, et al.
Neurogastroenterology and Motility, 26(8), 1079-1086 (2014)
A Randomized, Double-Blind, Placebo-Controlled, Phase 3 Trial to Evaluate the Efficacy, Safety, and Tolerability of Prucalopride in Men With Chronic Constipation.
Yiannakou Y, et al.
The American Journal of Gastroenterology, 110(5), 741-741 (2015)
Wael Noor El-Nachef et al.
Development (Cambridge, England), 147(13) (2020-06-17)
The enteric nervous system (ENS) is essential for normal gastrointestinal function. Although the embryonic origin of enteric neurons from the neural crest is well established, conflicting evidence exists regarding postnatal enteric neurogenesis. Here, we address this by examining the origin

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