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Also known as: Cb-839, 1439399-58-2, Telaglenastat [usan], Cb839, Cb 839, 2-(pyridin-2-yl)-n-(5-(4-(6-(2-(3-(trifluoromethoxy)phenyl)acetamido)pyridazin-3-yl)butyl)-1,3,4-thiadiazol-2-yl)acetamide

Molecular Formula

C₂₆H₂₄F₃N₇O₃S

Molecular Weight

571.6 g/mol

InChI Key

PRAAPINBUWJLGA-UHFFFAOYSA-N

FDA UNII

U6CL98GLP4

Telaglenastat is an orally bioavailable inhibitor of glutaminase, with potential antineoplastic activity. Upon oral administration, CB-839 selectively and irreversibly inhibits glutaminase, a mitochondrial enzyme that is essential for the conversion of the amino acid glutamine into glutamate. By blocking glutamine utilization, proliferation in rapidly growing cells is impaired. Glutamine-dependent tumors rely on the conversion of exogenous glutamine into glutamate and glutamate metabolites to both provide energy and generate building blocks for the production of macromolecules, which are needed for cellular growth and survival.

1 2D Structure

Telaglenastat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[6-[4-[5-[(2-pyridin-2-ylacetyl)amino]-1,3,4-thiadiazol-2-yl]butyl]pyridazin-3-yl]-2-[3-(trifluoromethoxy)phenyl]acetamide

2.1.2 InChI

InChI=1S/C26H24F3N7O3S/c27-26(28,29)39-20-9-5-6-17(14-20)15-22(37)31-21-12-11-18(33-34-21)7-1-2-10-24-35-36-25(40-24)32-23(38)16-19-8-3-4-13-30-19/h3-6,8-9,11-14H,1-2,7,10,15-16H2,(H,31,34,37)(H,32,36,38)

2.1.3 InChI Key

PRAAPINBUWJLGA-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=NC(=C1)CC(=O)NC2=NN=C(S2)CCCCC3=NN=C(C=C3)NC(=O)CC4=CC(=CC=C4)OC(F)(F)F

2.2 Other Identifiers

2.2.1 UNII

U6CL98GLP4

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cb-839

2.3.2 Depositor-Supplied Synonyms

1. Cb-839

2. 1439399-58-2

3. Telaglenastat [usan]

4. Cb839

5. Cb 839

6. 2-(pyridin-2-yl)-n-(5-(4-(6-(2-(3-(trifluoromethoxy)phenyl)acetamido)pyridazin-3-yl)butyl)-1,3,4-thiadiazol-2-yl)acetamide

7. U6cl98glp4

8. N-[6-[4-[5-[(2-pyridin-2-ylacetyl)amino]-1,3,4-thiadiazol-2-yl]butyl]pyridazin-3-yl]-2-[3-(trifluoromethoxy)phenyl]acetamide

9. 2-(pyridin-2-yl)-n-(5-{4-[6-({[3-(trifluoromethoxy)phenyl]acetyl}amino)pyridazin-3-yl]butyl}-1,3,4-thiadiazol-2-yl)acetamide

10. 2-pyridineacetamide, N-(5-(4-(6-((2-(3-(trifluoromethoxy)phenyl)acetyl)amino)-3-pyridazinyl)butyl)-1,3,4-thiadiazol-2-yl)-

11. 2-(pyridin-2-yl)-n-{5-[4-(6-{2-[3-(trifluoromethoxy)phenyl]acetamido}pyridazin-3-yl)butyl]-1,3,4-thiadiazol-2-yl}acetamide

12. 2-pyridineacetamide, N-[5-[4-[6-[[2-[3-(trifluoromethoxy)phenyl]acetyl]amino]-3-pyridazinyl]butyl]-1,3,4-thiadiazol-2-yl]-

13. 63j

14. N-(6-(4-(5-(2-(pyridin-2-yl)acetamido)-1,3,4-thiadiazol-2-yl)butyl)pyridazin-3-yl)-2-(3-(trifluoromethoxy)phenyl)acetamide

15. N-[6-(4-{5-[2-(pyridin-2-yl)acetamido]-1,3,4-thiadiazol-2-yl}butyl)pyridazin-3-yl]-2-[3-(trifluoromethoxy)phenyl]acetamide

16. Cb-839(telaglenastat)

17. Unii-u6cl98glp4

18. Telaglenastat [inn]

19. Telaglenastat (usan/inn)

20. Telaglenastat [who-dd]

21. Gtpl9053

22. Cb-839 [who-dd]

23. Chembl3639788

24. Schembl14987180

25. Bdbm109086

26. Hms3741e19

27. Hms3873g13

28. Amy16835

29. Bcp28287

30. Ex-a1310

31. Mfcd28167826

32. Nsc783415

33. Nsc795998

34. Nsc798057

35. S7655

36. Who 10815

37. Akos025396175

38. Zinc169698697

39. Ccg-270102

40. Cs-3393

41. Db15232

42. Nsc-783415

43. Nsc-795998

44. Nsc-798057

45. Sb17221

46. Ncgc00356145-11

47. 2-?pyridineacetamide, N-?[5-?[4-?[6-?[[2-?[3-?(trifluoromethoxy)?phenyl]?acetyl]?amino]?-?3-?pyridaz

48. Ac-31603

49. As-75090

50. Cb839; Cb 839 Pound>>telaglenastat,

51. Da-34988

52. Hy-12248

53. Ft-0767818

54. A14396

55. D11738

56. A857288

57. Us8604016, 670

58. Q27075751

59. 2-?pyridineacetamide, N-?[5-?[4-?[6-?[[2-?[3-?(trifluoromethoxy)?phenyl]?acetyl]?amino]?-?3-?pyridazinyl]?butyl]?-?1,?3,?4-?thiadiazol-?2-?yl]?-

60. N-[5-[4-[6-[[2-[3-(trifluoromethoxy)phenyl]acetyl]amino]-3-pyridazinyl]butyl]-1,3,4-thiadiazol-2-yl]-2-pyridineacetamide

61. N-[5-[4-[6-[[2-[3-(trifluoromethoxy)phenyl]acetyl]amino]-3-pyridazinyl]butyl]-1,3,4-thiadiazol-2-yl]-2-pyridineacetamide;cb-839

2.4 Create Date

2013-07-01

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₄F₃N₇O₃S
Molecular Weight	571.6 g/mol
XLogP3	3.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	12
Exact Mass	571.16134331 g/mol
Monoisotopic Mass	571.16134331 g/mol
Topological Polar Surface Area	160 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	812
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