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Elesclomol

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Synopsis

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Chemistry

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Also known as: 488832-69-5, Sta-4783, Elesclomol (sta-4783), N'1,n'3-dimethyl-n'1,n'3-di(phenylcarbonothioyl)malonohydrazide, Elesclomol [usan], Chebi:79369

Molecular Formula

C₁₉H₂₀N₄O₂S₂

Molecular Weight

400.5 g/mol

InChI Key

BKJIXTWSNXCKJH-UHFFFAOYSA-N

FDA UNII

6UK191M53P

Elesclomol is a small-molecule bis(thio-hydrazide amide) with oxidative stress induction, pro-apoptotic, and potential antineoplastic activities. Elesclomol induces oxidative stress, creating high levels of reactive oxygen species (ROS), such as hydrogen peroxide, in both cancer cells and normal cells. Because tumor cells have elevated levels of ROS compared to normal cells, the increase in oxidative stress beyond baseline levels elevates ROS beyond sustainable levels, exhausting tumor cell antioxidant capacity, which may result in the induction of the mitochondrial apoptosis pathway. Normal cells are spared because the increase in the level of oxidative stress induced by this agent is below the threshold at which apoptosis is induced.

1 2D Structure

Elesclomol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-N',3-N'-bis(benzenecarbonothioyl)-1-N',3-N'-dimethylpropanedihydrazide

2.1.2 InChI

InChI=1S/C19H20N4O2S2/c1-22(18(26)14-9-5-3-6-10-14)20-16(24)13-17(25)21-23(2)19(27)15-11-7-4-8-12-15/h3-12H,13H2,1-2H3,(H,20,24)(H,21,25)

2.1.3 InChI Key

BKJIXTWSNXCKJH-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C(=S)C1=CC=CC=C1)NC(=O)CC(=O)NN(C)C(=S)C2=CC=CC=C2

2.2 Other Identifiers

2.2.1 UNII

6UK191M53P

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Sta 4783

2. Sta-4783

3. Sta4783

2.3.2 Depositor-Supplied Synonyms

1. 488832-69-5

2. Sta-4783

3. Elesclomol (sta-4783)

4. N'1,n'3-dimethyl-n'1,n'3-di(phenylcarbonothioyl)malonohydrazide

5. Elesclomol [usan]

6. Chebi:79369

7. Propanedioic Acid, Bis[2-methyl-2-(phenylthioxomethyl)hydrazide]

8. 6uk191m53p

9. Gsk-842879a

10. Elesclomol (usan)

11. Gsk-842879

12. 1,3-bis[2-methyl-2-(phenylthioxomethyl)hydrazide]propanedioic Acid

13. 1-n',3-n'-bis(benzenecarbonothioyl)-1-n',3-n'-dimethylpropanedihydrazide

14. 1-n'-benzenecarbothioyl-3-(2-benzenecarbothioyl-2-methylhydrazinyl)-n'-methyl-oxopropanehydrazidide

15. Elesclomol [usan:inn]

16. Elesclomolum

17. Unii-6uk191m53p

18. N'1,n'3-dimethyl-n'1,n'3-bis(phenylcarbonothioyl)propanedihydrazide

19. Propanedioic Acid, Bis(2-methyl-2-(phenylthioxomethyl)hydrazide)

20. Sta4783

21. Sta 4783

22. Nsc174939

23. Elesclomol [mi]

24. Elesclomol [inn]

25. Elesclomol [mart.]

26. Elesclomol [who-dd]

27. Mls006011164

28. Schembl313745

29. Chembl1972860

30. Dtxsid2042642

31. Schembl10131773

32. Ex-a602

33. Hms3654m11

34. Hms3868i03

35. Bcp00247

36. Zinc1716098

37. Mfcd12911784

38. S1052

39. Akos005145783

40. Bcp9000639

41. Ccg-264795

42. Cs-0192

43. Db05719

44. Nsc-174939

45. Sb17208

46. Ncgc00183656-01

47. Ncgc00183656-02

48. Ncgc00183656-09

49. Ncgc00183656-11

50. Ac-35840

51. As-56232

52. Hy-12040

53. Nci60_001429

54. Smr004702933

55. Ft-0700480

56. Sw219775-1

57. Ec-000.2312

58. A23836

59. D08909

60. H11160

61. 832e695

62. J-503879

63. N-malonyl-bis (n'-methyl-n'-thiobenzoyl Hydrazide)

64. Q5359460

65. Brd-k82135108-001-01-9

66. N,n'-bis[methyl[phenyl(thiocarbonyl)]amino]malonamide

67. N'(1),n'(3)-dimethyl-n'(1),n'(3)-bis(phenylcarbonothioyl)malonohydrazide

68. 1-n'-benzenecarbothioyl-3-(2-benzene Carbothioyl-2-methylhydrazinyl)-n'-methyloxopropanehydrazidide

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₀N₄O₂S₂
Molecular Weight	400.5 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	400.10276824 g/mol
Monoisotopic Mass	400.10276824 g/mol
Topological Polar Surface Area	129 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	510
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 melanoma.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Elesclomol is a first-in-class heat shock protein 70 (Hsp70) inducer that activates natural killer (NK) cell-mediated tumor killing.

5.2 Mechanism of Action

Elesclomol acts through a novel mechanism of action. Elesclomol has been shown to rapidly cause a dramatic increase in oxidative stress (ROS) inside cancer cells. The prolonged elevation of ROS inside cancer cells induced by elesclomol causes the cell to exceed a critical breaking point and undergo apoptosis. The triggering of the mitochondrial apoptosis pathway is observed within the first six hours of applying elesclomol. Cancer cells operate at a much higher intrinsic level of ROS than normal cells, and have a greatly reduced anti-oxidant capacity compared to normal cells. This leaves them more vulnerable to an agent such as elesclomol that elevates oxidative stress. In similar experiments at similar doses, elesclomol has been found to have little to no impact on normal cells.

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