289656-45-7

Basic information

• Product Name: 2,2-bis(4-fluorophenyl)-2-phenyl-acetamide
• Synonyms: 2,2-bis(4-fluorophenyl)-2-phenyl-acetamide;ICA 17043;Senicapoc;Benzeneacetamide, 4-fluoro-a-(4-fluorophenyl)-a-phenyl-;4-Fluoro-alpha-(4-fluorophenyl)-alpha-phenylbenzeneacetamide;4-Fluoro-A-(4-Fluorophenyl)-A-Phenyl-BenzeneacetaMide
• CAS NO: 289656-45-7
• Molecular Formula: C20H15F2NO
• Molecular Weight: 323.34
• Mol File: 289656-45-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 180-181 °C(Solv: hexane (110-54-3); dichloromethane (75-09-2))
• Boiling Point: 460.7 °C at 760 mmHg
• Flash Point: 232.4 °C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 1.14E-08mmHg at 25°C
• Refractive Index: 1.594
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 15.41±0.50(Predicted)
• CAS DataBase Reference: 2,2-bis(4-fluorophenyl)-2-phenyl-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-bis(4-fluorophenyl)-2-phenyl-acetamide(289656-45-7)
• EPA Substance Registry System: 2,2-bis(4-fluorophenyl)-2-phenyl-acetamide(289656-45-7)

Safety Data

• Hazardous Substances Data: 289656-45-7(Hazardous Substances Data)

Usage

Description

Senicapoc is an inhibitor of intermediate conductance calcium-activated potassium (IKCa1/KCa3.1) channels. It inhibits rubidium efflux from and dehydration of isolated human red blood cells (RBCs) induced by the calcium ionophore A23187 (; IC50s = 11 and 30 nM, respectively). Senicapoc (10 mg/kg twice per day) reduces IKCa1/KCa3.1 channel activity, increases potassium levels in RBCs, and decreases erythrocyte density in the SAD transgenic mouse model of sickle cell disease. It inhibits IL-2, IFN-γ, IL-12, and IL-17A production in CD3+ T cells stimulated with phorbol 12-myristate 13-acetate (PMA; ) and ionomycin (Item Nos. 10004974 | 11932) when used at a concentration of 1 μM. Senicapoc (100 mg/kg) increases the paw withdrawal threshold in a rat model of chronic constriction injury (CCI) of the sciatic nerve.

Uses

Treatment of disorders mediated by a calcium activated intermediate conductance potassium ion channel antagonist.

InChI:InChI=1/C20H15F2NO/c21-17-10-6-15(7-11-17)20(19(23)24,14-4-2-1-3-5-14)16-8-12-18(22)13-9-16/h1-13H,(H2,23,24)

Upstream product

• 100-58-3 phenylmagnesium bromide 
• 289656-82-2 bis(4-fluorophenyl)phenylacetonitrile 
• 379-55-5 bis(4-fluorophenyl)phenylmethanol 
• 345-92-6 4,4'-Difluorobenzophenone 

Relevant articles and documents

Process development and optimization for production of a potassium ion channel blocker, ICA-17043

A scalable process for the manufacture of a potassium ion channel blocker was developed and optimized. Key features of the process include an optimized Grignard reaction, a direct cyanation of the intermediate trityl alcohol derivative, and an improved nitrile hydrolysis protocol, relative to the original acidic hydrolysis conditions, to generate the crude active pharmaceutical ingredient (API) with >95% HPLC purity. The Grignard and the cyanation reactions could be telescoped, resulting in an improved throughput compared to the original four-step process. An effective recrystallization of the API was also developed and the process scaled up to manufacture multiple batches at the pilot scale.