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    Elesclomol

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    PharmaCompass
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    2D Structure
    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

    2D Structure

    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 Weight 400.5 g/mol
    Molecular Formula C19H20N4O2S2
    XLogP32.9
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count4
    Exact Mass400.10276824 g/mol
    Monoisotopic Mass400.10276824 g/mol
    Topological Polar Surface Area129 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity510
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.