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Elesclomol

Elesclomol structure

CAS No:
488832-69-5
Formula:
C19H20N4O2S2
Chemical Name:
Elesclomol
Synonyms:
Propanedioic acid,1,3-bis[2-methyl-2-(phenylthioxomethyl)hydrazide];Propanedioic acid,bis[2-methyl-2-(phenylthioxomethyl)hydrazide];NSC 174939;Elesclomol;STA 4783;GSK 842879A;1-N′,3-N′-Bis(benzenecarbonothioyl)-1-N′,3-N′-dimethylpropanedihydrazide;874477-56-2
Categories:
Biochemical Engineering > Inhibitors

Description

Elesclomol is an oxidative stress inducer that induces cancer cell apoptosis.

Elesclomol is a carbohydrazide obtained by formal condensation of the carboxy groups of malonic acid with the hydrino groups of two molar equivalents of N-methylbenzenecarbothiohydrazide It has a role as an antineoplastic agent and an apoptosis inducer. It is a carbohydrazide and a thiocarbonyl compound. It derives from a malonic acid.|Elesclomol is a novel, injectable, drug candidate that kills cancer cells by elevating oxidative stress levels beyond a breaking point, triggering programmed cell death. In preclinical models elesclomol showed potent killing of a broad range of cancer cell types at high doses, and an ability to strongly enhance the efficacy of certain chemotherapy agents, with minimal additional toxicity, at moderate doses. It is being developed by Synta Pharmaceuticals.|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.

Elesclomol Basic Attributes

Molecular Weight：

400.52

Exact Mass：

400.52

UNII：

6UK191M53P

NSC Number：

174939

DSSTox ID：

DTXSID2042642

NCI Thesaurus Code：

C75291

Characteristics

PSA：

129

XLogP3：

1.98

Density：

1.3±0.1 g/cm3

Refractive Index：

1.668

Drug Information

Drug Indication：

Investigated for use/treatment in melanoma.

Pharmacology：

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

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.

MeSH Entry Terms：

elesclomol

Computed Properties

Molecular Weight:400.5
XLogP3:2.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:400.10276824
Monoisotopic Mass:400.10276824
Topological Polar Surface Area:129
Heavy Atom Count:27
Complexity:510
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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488832-69-5

CAS No.: 488832-69-5

Content: 98%

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