Imidafenacin

Base Information

• Chemical Name: Imidafenacin
• CAS No.: 170105-16-5
• Molecular Formula: C20H21N3O
• Molecular Weight: 319.406
• European Community (EC) Number: 689-703-7
• UNII: XJR8Y07LJO
• DSSTox Substance ID: DTXSID00870104
• Nikkaji Number: J1.195.655F
• Wikipedia: Imidafenacin
• Wikidata: Q6003989
• NCI Thesaurus Code: C83789
• Pharos Ligand ID: MK7HUB5GK176
• Metabolomics Workbench ID: 152289
• ChEMBL ID: CHEMBL53366
• Mol file: 170105-16-5.mol

Synonyms:imidafenacin;KRP 197;KRP-197

Chemical Property of Imidafenacin

Chemical Property:

• Vapor Pressure: 1.96E-13mmHg at 25°C
• Refractive Index: 1.602
• Boiling Point: 579.709 °C at 760 mmHg
• PKA: 15.72±0.50(Predicted)
• Flash Point: 304.397 °C
• PSA: 61.90000
• Density: 1.128 g/cm³
• LogP: 4.20290
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO, Methanol
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 319.168462302
• Heavy Atom Count: 24
• Complexity: 395

Purity/Quality:

99% ^*data from raw suppliers

Imidafenacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC=CN1CCC(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)N
• Recent ClinicalTrials: A Registry Study of Patients Initiating a Course of Drug Therapy for Overactive Bladder in Taiwan, Korea and China
• Recent NIPH Clinical Trials: Combined effect of vibegron and imidafenacin
• Description: Imidafenacin, an M3/M1 muscarinic receptor antagonist, was introduced in Japan for the oral treatment of OAB. The majority of OAB symptoms are thought to result from overactivity of the detrusor muscle, which is primarily mediated by acetylcholine-induced stimulation of muscarinic M3 receptors in the bladder. Previously marketed muscarinic antagonists for OAB include propiverine, tolterodine, oxybutynin, trospium, darifenacin, and solifenacin. In vitro, imidafenacin is equally active against M1 and M3 receptors (Kb＝0.32 and 0.55nM, respectively), and approximately 10-fold less active against M2 receptors (Kb＝4.13nM). Imidafenacin is chemically synthesized in three steps starting with alkylation of diphenylacetonitrile with dibromoethane, followed by condensation with 2-methylimidazole, and hydrolysis of the cyano group to a carboxamide group with 70% sulfuric acid.
• Uses: A novel therapeutic agent for overactive bladder with antimuscarinic activity, on mediator release from urothelium and detrusor overactivity induced by cerebral infarction. A muscarinic antagonist. Imidafenacin-d10 is deutirium labelled imidafenacin which is a novel therapeutic agent for overactive bladder with antimuscarinic activity, on mediator release from urothelium and detrusor overactivity induced by cerebral infarction.

Technology Process of Imidafenacin

There total 10 articles about Imidafenacin 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: 92.0%

4-(2-methyl-1-imidazolyl)-2,2-diphenylbutanamide hydrochloride (893421-54-0) → imidafenacin (170105-16-5)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 15 - 20 ℃; for 2h; Product distribution / selectivity; Charcoal; Cellulose powder;

Reference yield: 89.9%

4-(2-methyl-1-imidazolyl)-2,2-diphenylbutyronitrile methanesulfonate → imidafenacin (170105-16-5)

Guidance literature:

With potassium hydroxide; In isopropyl alcohol; for 7.5h; Reflux;

Reference yield: 86.4%

4-(2-methyl-1-imidazolyl)-2,2-diphenylbutyronitrile phosphate (562091-56-9) → imidafenacin (170105-16-5)

Guidance literature:

4-(2-methyl-1-imidazolyl)-2,2-diphenylbutyronitrile phosphate; With potassium hydroxide; In water; isopropyl alcohol; at 15 ℃; for 5h; Heating / reflux;

With hydrogenchloride; In water; isopropyl alcohol; at 15 - 50 ℃; for 1h; Product distribution / selectivity;

upstream raw materials:

4-(2-methyl-1H-imidazol-1-yl)-2,2-diphenylbutanenitrile

4-bromo-2,2-diphenylbutyronitrile

Diphenylacetonitrile

4-(2-methyl-1-imidazolyl)-2,2-diphenylbutyronitrile phosphate

Downstream raw materials:

4-(2-methyl-1-imidazolyl)-2,2-diphenylbutanamide hydrochloride

4-(2-methyl-1-imidazolyl)-2,2-diphenylbutanamide phosphate

4-(2-Methyl-imidazol-1-yl)-2,2-diphenyl-butyric acid methyl ester

Refernces

• 1、 -. "4-(2-METHYL-1H-IMIDAZOL-1-YL)-2,2-DIPHENYLBUTANENITRILE SOLID FORM". . . Retrieved 2016/09/26.
• 2、 -. "METHOD FOR PRODUCING 4-(2-METHYL-1-IMIDAZOLYL)-2,2-PHENYLBUTANE AMIDE". . . Retrieved 2016/12/22.