Prucalopride

Base Information

• Chemical Name: Prucalopride
• CAS No.: 179474-81-8
• Molecular Formula: C18H26ClN3O3
• Molecular Weight: 367.876
• European Community (EC) Number: 878-837-3
• UNII: 0A09IUW5TP
• DSSTox Substance ID: DTXSID5057670
• Nikkaji Number: J1.158.495K
• Wikipedia: Prucalopride
• Wikidata: Q68484
• NCI Thesaurus Code: C74386
• RXCUI: 2107310
• Pharos Ligand ID: P654KZGW7U5W
• Metabolomics Workbench ID: 149802
• ChEMBL ID: CHEMBL117287
• Mol file: 179474-81-8.mol

Synonyms:Prucalopride;R 093877;

Chemical Property of Prucalopride

Chemical Property:

• Vapor Pressure: 2E-09mmHg at 25°C
• Melting Point: 90.7°
• Refractive Index: 1.599
• Boiling Point: 481.369 °C at 760 mmHg
• PKA: 13.65±0.20(Predicted)
• Flash Point: 244.923 °C
• PSA: 76.82000
• Density: 1.286 g/cm³
• LogP: 2.99780
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 367.1662694
• Heavy Atom Count: 25
• Complexity: 445

Purity/Quality:

99% ^*data from raw suppliers

Prucalopride 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Gastrointestinal Agents
• Canonical SMILES: COCCCN1CCC(CC1)NC(=O)C2=CC(=C(C3=C2OCC3)N)Cl
• Recent ClinicalTrials: A Study of Prucalopride For Functional Constipation in Children and Teenagers
• Recent EU Clinical Trials: Characterization of nerve-modulated macrophage population in the gastrointestinal tract
• 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). 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 and granisetron , respectively. 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. Formulations containing prucalopride have been used in the treatment of chronic idiopathic constipation.

Technology Process of Prucalopride

There total 27 articles about Prucalopride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

4-amino-1-(3-methoxypropyl)piperidine (179474-79-4) + 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid (123654-26-2) → prucalopride (179474-81-8)

Guidance literature:

4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; for 0.416667h;

4-amino-1-(3-methoxypropyl)piperidine; In tetrahydrofuran; at 45 - 50 ℃; for 4h;

Reference yield:

4-amino-5-chloro-2,3-dihydro-N-(4-piperidinyl)benzofuran-7-carboxamide (137211-64-4) + 1-Chloro-3-methoxypropane (36215-07-3) → prucalopride (179474-81-8)

Guidance literature:

With triethylamine; potassium iodide; In N,N-dimethyl-formamide; at 90 - 95 ℃;

Reference yield:

4-amino-1-(3-methoxypropyl)piperidine (179474-79-4) + 4-amino-5-chloro-7-aldehyde-2,3-dihydrobenzofuran → prucalopride (179474-81-8)

Guidance literature:

With tert.-butylhydroperoxide; calcium carbonate pentahydrate; In acetonitrile; at 80 ℃; for 8h;

upstream raw materials:

ethyl 1-(3-methoxy-propyl)-piperidin-4-carboxylate

4-amino-1-(3-methoxypropyl)piperidine

4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid

4-acetamido-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid methyl ester

Downstream raw materials:

prucalopride succinate

Refernces

• 1、 -. "Preparation method of prucalopride succinate". . . Retrieved 2019/01/08.
• 2、 -. "A process for the preparation of intermediate the Pu card must benefit new process (by machine translation)". . . Retrieved 2017/07/20.