Elesclomol

Elesclomol

Systematic (IUPAC) name
N′1,N′3-dimethyl-N′1,N′3- bis(phenylcarbonothioyl)propanedihydrazide
Identifiers
CAS Number	488832-69-5 Y
ATC code	none
PubChem	CID: 300471
ChemSpider	265501 Y
UNII	6UK191M53P Y
ChEBI	CHEBI:79369 N
ChEMBL	CHEMBL1972860 N
Chemical data
Formula	C19H20N4O2S2
Molecular mass	400.518 g/mol
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) Y Key:BKJIXTWSNXCKJH-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Elesclomol (INN, codenamed STA-4783) is a drug that triggers apoptosis (programmed cell death) in cancer cells. It is being developed by Synta Pharmaceuticals and GlaxoSmithKline as a chemotherapy adjuvant, and has received both fast track and orphan drug status from the U.S. Food and Drug Administration for the treatment of metastatic melanoma. Synta Pharmaceuticals announced on February 26, 2009 the suspension of all clinical trials involving Elesclomol due to safety concerns. In March 2010, Synta announced that the FDA had approved resuming clinical development of elesclomol, and that they expected to initiate one or more clinical trials for elesclomol in the second half of the year.

In a small, randomized phase II study, elesclomol was shown to significantly increase progression-free survival in people with metastatic melanoma when given in addition to paclitaxel (Taxol).

Mechanism of action

Elesclomol induces oxidative stress by provoking a buildup of reactive oxygen species within cancer cells. Elesclomol requires a redox active metal ion to function. The Cu(II) complex is 34 times more potent than the Ni(II) complex and 1040-fold more potent than the Pt(II) complex.

Discovery

Elesclomol was first synthesized at Taras Shevchenko National University in Kiev, Ukraine. It's efficiency against cancer was discovered by taiwaneese cell biologist Lan Bo Chen who purchased a batch of eleschomol, among tens of thousands of other compounds, for the purpose of mass drug screening. “It was pure chemist’s joy,” Chen later said. “Homemade, random, and clearly made for no particular purpose. It was the only one that worked on everything we tried.”