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Chemistry

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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

Tomivosertib

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 Formula	C₁₇H₂₀N₆O₂
Molecular Weight	340.4 g/mol
XLogP3	1.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	340.16477390 g/mol
Monoisotopic Mass	340.16477390 g/mol
Topological Polar Surface Area	113 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	664
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