Senicapoc

Base Information

• Chemical Name: Senicapoc
• CAS No.: 289656-45-7
• Molecular Formula: C₂₀H₁₅F₂NO
• Molecular Weight: 323.342
• Hs Code.: 2924299090
• UNII: TS6G201A6Q
• DSSTox Substance ID: DTXSID60276906
• Wikipedia: Senicapoc
• Wikidata: Q7450628
• NCI Thesaurus Code: C76882
• Pharos Ligand ID: D3YZBR54CQYF
• Metabolomics Workbench ID: 149720
• ChEMBL ID: CHEMBL405821
• Mol file: 289656-45-7.mol

Synonyms:bis(4-fluorophenyl)phenylacetamide;ICA 17043;ICA-17043;ICA17043;senicapoc

Chemical Property of Senicapoc

Chemical Property:

• Vapor Pressure: 1.14E-08mmHg at 25°C
• Melting Point: 180-181 °C(Solv: hexane (110-54-3); dichloromethane (75-09-2))
• Refractive Index: 1.594
• Boiling Point: 460.7 °C at 760 mmHg
• PKA: 15.41±0.50(Predicted)
• Flash Point: 232.4 °C
• PSA: 43.09000
• Density: 1.25g/cm³
• LogP: 4.48480
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 323.11217043
• Heavy Atom Count: 24
• Complexity: 397

Purity/Quality:

97% ^*data from raw suppliers

2,2-Bis(4-fluorophenyl)-2-phenylacetamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=C(C=C2)F)(C3=CC=C(C=C3)F)C(=O)N
• Recent ClinicalTrials: Senicapoc in Alzheimer's Disease
• Recent EU Clinical Trials: Senicapoc in COVID-19 Patients with Severe Respiratory Insufficiency
• 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.

Technology Process of Senicapoc

There total 10 articles about Senicapoc 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: 58.0%

→ Senicapoc (289656-45-7)

Guidance literature:

Reference yield:

phenylmagnesium bromide (100-58-3) → Senicapoc (289656-45-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: toluene; tetrahydrofuran / 20 - 50 °C / Large scale

2.1: indium(III) chloride / toluene / 0.5 h / 20 °C / Large scale

2.2: 2.5 h / 20 - 40 °C / Large scale

3.1: potassium hydroxide / tert-Amyl alcohol / 10.5 h / 85 - 95 °C / Large scale

With indium(III) chloride; potassium hydroxide; In tetrahydrofuran; tert-Amyl alcohol; toluene;

DOI:10.1021/op3000916

Reference yield:

4,4'-Difluorobenzophenone (345-92-6) → Senicapoc (289656-45-7) + bis-(4-fluoro-phenyl)-phenyl-methane (386-95-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: toluene; tetrahydrofuran / 20 - 50 °C / Large scale

2.1: indium(III) chloride / toluene / 0.5 h / 20 °C / Large scale

2.2: 2.5 h / 20 - 40 °C / Large scale

3.1: potassium hydroxide / tert-Amyl alcohol / 12 h / 100 °C

With indium(III) chloride; potassium hydroxide; In tetrahydrofuran; tert-Amyl alcohol; toluene;

DOI:10.1021/op3000916

upstream raw materials:

4,4'-Difluorobenzophenone

bis(4-fluorophenyl)phenylmethanol

bis(4-fluorophenyl)phenylacetonitrile

phenylmagnesium bromide