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1 Drugs in Development

Synopsis

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Chemistry

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Also known as: 289656-45-7, 2,2-bis(4-fluorophenyl)-2-phenylacetamide, Ica-17043, Senicapoc (usan), Senicapoc [usan], Ts6g201a6q

Molecular Formula

C₂₀H₁₅F₂NO

Molecular Weight

323.3 g/mol

InChI Key

SCTZUZTYRMOMKT-UHFFFAOYSA-N

FDA UNII

TS6G201A6Q

Senicapoc is an orally bioavailable inhibitor of the calcium-activated potassium channel KCa3.1 (Gardos channel; KCNN4; IK-1; SK4), with potential anti-inflammatory and immunomodulatory activities. Upon oral administration, senicapoc targets, binds to and inhibits KCa3.1. KCa3.1 regulates membrane potential and calcium signaling in a variety of cells including erythrocytes, activated T and B cells, macrophages, microglia, vascular endothelium, epithelia, and proliferating vascular smooth muscle cells and fibroblasts. The inhibition of KCa3.1 may prevent erythrocyte dehydration in sickle cell disease, reduce fluid secretion, fluid retention and inflammation in the lungs in acute respiratory distress syndrome (ARDS), and reduce inflammation and immune responses in various other diseases such as neuroinflammation in Alzheimer's disease. Senicapoc exhibits good brain penetration.

1 2D Structure

Senicapoc

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,2-bis(4-fluorophenyl)-2-phenylacetamide

2.1.2 InChI

InChI=1S/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)

2.1.3 InChI Key

SCTZUZTYRMOMKT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C(C=C1)C(C2=CC=C(C=C2)F)(C3=CC=C(C=C3)F)C(=O)N

2.2 Other Identifiers

2.2.1 UNII

TS6G201A6Q

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bis(4-fluorophenyl)phenylacetamide

2. Ica 17043

3. Ica-17043

4. Ica17043

2.3.2 Depositor-Supplied Synonyms

1. 289656-45-7

2. 2,2-bis(4-fluorophenyl)-2-phenylacetamide

3. Ica-17043

4. Senicapoc (usan)

5. Senicapoc [usan]

6. Ts6g201a6q

7. Pf-05416266

8. Benzeneacetamide, 4-fluoro-alpha-(4-fluorophenyl)-alpha-phenyl-

9. Bis(4-fluorophenyl)phenylacetamide

10. Senicapoc [usan:inn]

11. Ica 17043

12. Unii-ts6g201a6q

13. 2,2-bis(4-fluorophenyl)-2-phenyl-acetamide

14. 4-fluoro-alpha-(4-fluorophenyl)-alpha-phenylbenzeneacetamide

15. Senicapoc [inn]

16. Senicapoc [mart.]

17. Senicapoc [who-dd]

18. Chembl405821

19. Gtpl2331

20. Schembl1443805

21. Amy2744

22. Dtxsid60276906

23. Hms3741e13

24. Act06676

25. Bcp14507

26. Zinc3816408

27. Bbl102413

28. Bdbm50371391

29. Mfcd09027349

30. Stl556215

31. Akos007930800

32. Cs-0294

33. Db06280

34. 4-methyl-1h-pyrrole-2-carboxylic?acid

35. Hy-50694

36. Ms-20434

37. Db-003217

38. Ft-0660387

39. 2,2-bis(4-fluorophenyl)-2-phenyl-ethanamide

40. C74487

41. D06640

42. 656f457

43. A822267

44. A904983

45. Au-004/43508060

46. Q7450628

47. 4-fluoro-a-(4-fluorophenyl)-a-phenyl-benzeneacetamide

2.4 Create Date

2005-08-09

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₅F₂NO
Molecular Weight	323.3 g/mol
XLogP3	4.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Exact Mass	323.11217043 g/mol
Monoisotopic Mass	323.11217043 g/mol
Topological Polar Surface Area	43.1 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	397
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in anemia (sickle cell) and asthma.

Drugs in Development

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Senicapoc

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