| 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(179474-81-8) 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. | [Mechanism of action]
Prucalopride(179474-81-8) is a high affinity, highly selective 5-HT4 agonist. Its action in the treatment of chronic constipation is to stimulate intestinal peristalsis by specifically interacting with 5-HT4 receptors in the digestive tract, resulting in the release of acetylcholine, which further constricts the muscular layer of the colon, and the relaxation of the circular muscular layer promoting the expulsion of luminal contents.
| [Side effects]
Prucalopride(179474-81-8) is usually well tolerated. The most common adverse reactions include: headache, nausea, abdominal pain and diarrhoea. Other adverse reactions that may occur include: abnormal stomach or bowel sounds, flatulence, decreased appetite, dizziness, unusual tiredness or weakness, pain in the extremities or chest, difficulty or inability to speak, difficulty breathing, and suicidal thoughts. Severe allergic reactions are rare and usually manifest as hives or lumps, itching, rash, redness of the skin, swelling of the face, and tightness in the chest.
| [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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