| Identification | Back Directory | [Name]
Prucalopride | [CAS]
179474-81-8 | [Synonyms]
CS-219
Resolor
R093877
R 093877
Prucalopride
Unii-0A09iuw5tp
Prucalopride, >=98%
Prucalopride(R-93877)
Prucalopride USP/EP/BP
Prucalopride, 99%, a 5-HT Receptor agonist
4-Amino-5-chloro-2,3-dihydro-N-(1-(3-methoxypropyl)-4-piperidyl)-7-benzofurancarboxamide
4-Amino-5-chloro-2,3-dihydro-N-[1-(3-methoxypropyl)-4-piperidinyl]-7-benzofurancarboxamide
4-Amino-5-chloro-N-(1-(3-methoxypropyl)piperidin-4-yl)-2,3-dihydrobenzofuran-7-carboxamide
7-BenzofurancarboxaMide, 4-aMino-5-chloro-2,3-dihydro-N-[1-(3-Methoxypropyl)-4-piperidinyl]-
4-amino-5-chloro-N-[1-(3-methoxypropyl)piperidin-4-yl]-2,3-dihydro-1-benzofuran-7-carboxamide | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C18H26ClN3O3 | [MDL Number]
MFCD09837787 | [MOL File]
179474-81-8.mol | [Molecular Weight]
367.874 |
| Chemical Properties | Back Directory | [Melting point ]
90.7° | [Boiling point ]
481.4±45.0 °C(Predicted) | [density ]
1.28 | [storage temp. ]
2-8°C | [solubility ]
DMF: 20 mg/ml; DMF:PBS (pH 7.2) (1:9): 0.1 mg/ml; DMSO: 10 mg/ml; Ethanol: 10 mg/ml | [form ]
powder | [pka]
13.65±0.20(Predicted) | [color ]
white to beige | [InChI]
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) | [InChIKey]
ZPMNHBXQOOVQJL-UHFFFAOYSA-N | [SMILES]
O1C2=C(C(NC3CCN(CCCOC)CC3)=O)C=C(Cl)C(N)=C2CC1 |
| Hazard Information | Back Directory | [Description]
Prucalopride is a potent and selective agonist of the serotonin (5-HT) receptor subtype 5-HT4 (Kis = 2.5 and 8 nM for human 5-HT4A and 5-HT4B, respectively).1 Prucalopride is greater than 250-fold selective for 5-HT4 over a panel of 53 overexpressed receptors, including 5-HT subtypes, but does bind to human dopamine D4 and sigma-1 (σ1) receptors and mouse 5-HT3 receptors (Kis = 2.3, 3.7, and 3.8 μM, respectively). It induces contractions in guinea pig colon with an EC50 value of 33 nM, an effect that is blocked by the 5-HT4 antagonist GR113808 but not the 5-HT2A and 5-HT3 antagonists ketanserin (Item No. 22058) and granisetron (Item No. 21239), respectively.2 It also facilitates non-cholinergic contractions induced by electrical stimulation. In fasted dogs, oral administration of prucalopride increases colonic motility by inhibiting distal colon contractions (ED50 = 0.04 mg/kg), an effect that is blocked by pretreatment with the 5-HT4 antagonist GR125487. Prucalopride (5-10 mg/kg, s.c.) increases acetylcholine and histamine levels in the rat prefrontal cortex by 2.4-fold and 3-fold, respectively, and increases the power of hippocampal theta oscillations.3 Formulations containing prucalopride have been used in the treatment of chronic idiopathic constipation. | [Definition]
ChEBI: Prucalopride is a member of benzamides. | [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. | [Enzyme inhibitor]
This novel enterokinetic drug (FW = 367.87 g/mol; CAS 179474-81-8),
®
also known by the tradename Resolor and its systematic name, 4-amino-5-
chloro-N-[1- (3-methoxypropyl) piperidin-4-yl]-2,3-dihydro-1-benzofuran-7-
carboxamide, is a selective, high affinity serotonin 5-HT4 receptor agonist
with that stimulates colonic mass movements, which provide the main
propulsive force for defecation. It exhibits high affinity to both 5-HT4
receptor isoforms, with respective pKi values of 8.60 and 8.10 for the
human 5-HT4A and 5-HT4B receptors. Based on 50 other binding
assays,tonly the human D4 receptor (pKi = 5.63), the mouse 5-HT3 receptor
(pKi = 5.41) and the human s1 (pKi = 5.43) shown measurable affinity,
resulting in >290x selectivity for 5-HT4 receptors. Prucalopride also differs
from other 5-HT4 agonists, such as tegaserod and cisapride, that interact
with other receptors (5-HT1B/D and cardiac human ether-a-go-go K+ or
hERG channel, respectively). | [storage]
Store at -20°C |
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