Rigosertib

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Also known as: 592542-59-1, On-01910, On 01910, Rigosertib [usan], 67dow7f9gl, Rigosertib (usan)

Molecular Formula

C₂₁H₂₅NO₈S

Molecular Weight

451.5 g/mol

InChI Key

OWBFCJROIKNMGD-BQYQJAHWSA-N

FDA UNII

67DOW7F9GL

Rigosertib is a synthetic benzyl styryl sulfone analogue and Ras mimetic, with potential antineoplastic activity. Upon administration, rigosertib targets and binds to Ras-binding domain (RBD) found in many Ras effector proteins, including Raf kinase and phosphatidylinositol 3-kinase (PI3K). This prevents Ras from binding to its targets and inhibits Ras-mediated signaling pathways, including Ras/Raf/Erk, Ras/CRAF/polo-like kinase1 (Plk1), and Ras/ PI3K/Akt signaling pathways. This induces cell cycle arrest and apoptosis and inhibits proliferation in a variety of susceptible tumor cells.

1 2D Structure

Rigosertib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[2-methoxy-5-[[(E)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonylmethyl]anilino]acetic acid

2.1.2 InChI

InChI=1S/C21H25NO8S/c1-27-15-10-19(29-3)16(20(11-15)30-4)7-8-31(25,26)13-14-5-6-18(28-2)17(9-14)22-12-21(23)24/h5-11,22H,12-13H2,1-4H3,(H,23,24)/b8-7+

2.1.3 InChI Key

OWBFCJROIKNMGD-BQYQJAHWSA-N

2.1.4 Canonical SMILES

COC1=C(C=C(C=C1)CS(=O)(=O)C=CC2=C(C=C(C=C2OC)OC)OC)NCC(=O)O

2.1.5 Isomeric SMILES

COC1=C(C=C(C=C1)CS(=O)(=O)/C=C/C2=C(C=C(C=C2OC)OC)OC)NCC(=O)O

2.2 Other Identifiers

2.2.1 UNII

67DOW7F9GL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (n-(2-methyloxy-5-(2',4',6'-trimethoxystyrylsulfonyl)methylenephenyl)amino)acetic Acid

2. N-(2-methoxy-5-((((e)-2-(2,4,6-trimethoxyphenyl)vinyl)sulfonyl)methyl)phenyl)glycine

3. On 01910

4. On 01910.na

5. On-01910

6. On01910

7. Rigosertib Sodium

8. Sodium (n-(2-methyloxy-5-(2',4',6'-trimethoxystyrylsulfonyl)methylenephenyl)amino)acetate

2.3.2 Depositor-Supplied Synonyms

1. 592542-59-1

2. On-01910

3. On 01910

4. Rigosertib [usan]

5. 67dow7f9gl

6. Rigosertib (usan)

7. 2-[2-methoxy-5-[[(e)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonylmethyl]anilino]acetic Acid

8. (e)-2-((2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)phenyl)amino)acetic Acid

9. N-[2-methoxy-5-({[(e)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonyl}methyl)phenyl]glycine

10. N-[2-methoxy-5-[[[(1e)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonyl]methyl]phenyl]glycine

11. Rigosertib [usan:inn]

12. Unii-67dow7f9gl

13. Rigosertibum

14. 6fs

15. N-(2-methoxy-5-((((1e)-2-(2,4,6-trimethoxyphenyl)ethenyl)sulfonyl)methyl)phenyl)glycine

16. Rigosertib [inn]

17. Rigosertib [who-dd]

18. Estybon (proposed Trade Name)

19. Schembl498623

20. Schembl498624

21. Gtpl7833

22. Chembl1241855

23. On01910.na

24. Dtxsid30207984

25. 2-[2-methoxy-5-[2-(2,4,6-trimethoxyphenyl)ethenylsulfonylmethyl]anilino]acetic Acid

26. Chebi:124939

27. Chebi:145417

28. Bcp08296

29. Ex-a4346

30. Zinc3942646

31. Bdbm50060917

32. Akos015966442

33. Db12146

34. Glycine, N-[2-methoxy-5-[[[(1e)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonyl]methyl]phenyl]-

35. (e)-on 01910

36. 2-[[2-methoxy-5-[[(e)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonylmethyl]phenyl]amino]acetic Acid

37. Ac-32479

38. As-35249

39. On-01910on-01910

40. D10154

41. On-01910;on01910;on 01910

42. Brd-k55187425-236-01-1

43. Q21099552

44. (e)-2-(5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenylamino)acetic Acid

45. [2-methoxy-5-({[(e)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonyl}methyl)anilino]acetic Acid

46. [2-methoxy-5-({[2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonyl}methyl)anilino]acetic Acid

47. N-(2-methoxy-5-((((1e)-2-(2,4,6-trimethoxyphenyl)ethenyl)sulfonyl)methyl) Phenyl)glycine

48. N-[2-methoxy-5-({[2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonyl}methyl)phenyl]glycine

49. Glycine, N-(2-methoxy-5-((((1e)-2-(2,4,6-trimethoxyphenyl)ethenyl)sulfonyl) Methyl)phenyl)-

2.4 Create Date

2006-07-28

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₅NO₈S
Molecular Weight	451.5 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	11
Exact Mass	451.13008793 g/mol
Monoisotopic Mass	451.13008793 g/mol
Topological Polar Surface Area	129 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	678
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1