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2D Structure
Also known as: Eft508, 1849590-01-7, Eft-508, Tomivosertib [inn], Tomivosertib [usan], Eft 508
Molecular Formula
C17H20N6O2
Molecular Weight
340.4  g/mol
InChI Key
HKTBYUWLRDZAJK-UHFFFAOYSA-N
FDA UNII
U2H19X4WBV

Tomivosertib is an orally bioavailable inhibitor of mitogen-activated protein kinase (MAPK)-interacting serine/threonine-protein kinase 1 (MNK1) and 2 (MNK2), with potential antineoplastic activity. Upon oral administration, tomivosertib binds to and inhibits the activity of MNK1 and 2. This prevents MNK1/2-mediated signaling, and inhibits the phosphorylation of certain regulatory proteins, including eukaryotic translation initiation factor 4E (eIF4E), that regulate the translation of messenger RNAs (mRNAs) involved in tumor cell proliferation, angiogenesis, survival and immune signaling. This inhibits tumor cell proliferation in MNK1/2-overexpressing tumor cells. MNK1/2 are overexpressed in a variety of tumor cell types and promote phosphorylation of eIF4E; eIF4E is overexpressed in many tumor cell types and contributes to tumor development, maintenance and resistance.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
6-[(6-aminopyrimidin-4-yl)amino]-8-methylspiro[2H-imidazo[1,5-a]pyridine-3,1'-cyclohexane]-1,5-dione
2.1.2 InChI
InChI=1S/C17H20N6O2/c1-10-7-11(21-13-8-12(18)19-9-20-13)16(25)23-14(10)15(24)22-17(23)5-3-2-4-6-17/h7-9H,2-6H2,1H3,(H,22,24)(H3,18,19,20,21)
2.1.3 InChI Key
HKTBYUWLRDZAJK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=C2C(=O)NC3(N2C(=O)C(=C1)NC4=NC=NC(=C4)N)CCCCC3
2.2 Other Identifiers
2.2.1 UNII
U2H19X4WBV
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 6'-((6-amino-4-pyrimidinyl)amino)-8'-methyl-2'h-spiro(cyclohexane-1,3'-imidazo(1,5-a)pyridine)-1',5'-dione

2. Eft508

3. Spiro(cyclohexane-1,3'(2'h)-imidazo(1,5-a)pyridine)-1',5'-dione, 6'-((6-amino-4-pyrimidinyl)amino)-8'-methyl-

2.3.2 Depositor-Supplied Synonyms

1. Eft508

2. 1849590-01-7

3. Eft-508

4. Tomivosertib [inn]

5. Tomivosertib [usan]

6. Eft 508

7. U2h19x4wbv

8. Chembl4073443

9. 6'-((6-aminopyrimidin-4-yl)amino)-8'-methyl-1'h-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-1',5'(2'h)-dione

10. 6-[(6-aminopyrimidin-4-yl)amino]-8-methylspiro[2h-imidazo[1,5-a]pyridine-3,1'-cyclohexane]-1,5-dione

11. Eft508 Hcl

12. 6'-[(6-aminopyrimidin-4-yl)amino]-8'-methyl-2'h-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-1',5'-dione

13. Spiro(cyclohexane-1,3'(2'h)-imidazo(1,5-a)pyridine)-1',5'-dione, 6'-((6-amino-4-pyrimidinyl)amino)-8'-methyl-

14. Eft508; Tomivosertib

15. Tomivosertib (usan/inn)

16. Tomivosertib [usan:inn]

17. Eft-508 Hcl

18. Unii-u2h19x4wbv

19. Tomivosertib [who-dd]

20. Schembl17362622

21. Gtpl10167

22. Eft-508 (eft508)

23. Dtxsid601022534

24. Bcp18993

25. Ex-a2494

26. Bdbm50263263

27. Nsc791783

28. Nsc791784

29. Nsc804952

30. Zinc575623807

31. Ccg-267922

32. Cs-5841

33. Db15219

34. Nsc-791783

35. Nsc-791784

36. Nsc-804952

37. Compound 23 [pmid: 29526098]

38. Ncgc00492296-03

39. Ac-35882

40. Be168437

41. Bs-16162

42. Hy-100022

43. S8275

44. D11452

45. D71143

46. A902706

47. 6'-((6-aminopyrimidin-4-yl)amino)-8'-methyl-2'hspiro(cyclohexane-1,3'-imidazo(1,5-a)pyridine)-1',5'-dione

48. N45

2.4 Create Date
2016-02-23
3 Chemical and Physical Properties
Molecular Weight 340.4 g/mol
Molecular Formula C17H20N6O2
XLogP31.3
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass340.16477390 g/mol
Monoisotopic Mass340.16477390 g/mol
Topological Polar Surface Area113 Ų
Heavy Atom Count25
Formal Charge0
Complexity664
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1