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Details

Stereochemistry ACHIRAL
Molecular Formula C19H20N4O2S2
Molecular Weight 400.518
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELESCLOMOL

SMILES

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

InChI

InChIKey=BKJIXTWSNXCKJH-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18723479 http://adisinsight.springer.com/drugs/800018097

Elesclomol (also known as STA-4783), originally identified in a cell-based phenotypic screen for pro-apoptotic activity, is a novel small-molecule that potently induces apoptosis of cancer cells through the rapid generation of reactive oxygen species (ROS) and the induction of unmanageable levels of oxidative stress. Elesclomol exhibits antitumor activity against a broad spectrum of types of cancer cell in human tumour xenograft models due to its excessive ROS production and elevated levels of oxidative stress leading to the death of cancer cells. Elesclomol is currently being studied as novel cancer therapeutic, in which it has demonstrated the ability to prolong progression-free survival in study subjects. 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. Elesclomol is an HSP-90 Inhibitor with pro-apoptotic and potential antineoplastic activities. Elesclomol induces oxidative stress and triggers mitochondrial-induced apoptosis in cancer cells. Elesclomol 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).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
110.0 nM [IC50]
9.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Drug evaluation: STA-4783--enhancing taxane efficacy by induction of Hsp70.
2006 Jun
Phase I clinical trial of STA-4783 in combination with paclitaxel in patients with refractory solid tumors.
2007 Jan 15
Elesclomol induces cancer cell apoptosis through oxidative stress.
2008 Aug
Phase II, randomized, controlled, double-blinded trial of weekly elesclomol plus paclitaxel versus paclitaxel alone for stage IV metastatic melanoma.
2009 Nov 10
Patents

Patents

Sample Use Guides

213 mg/m2 Elesclomol (STA-4783) plus 80 mg/m2 paclitaxel administered intravenously once a week for the first 3 weeks of a 4 week cycle.
Route of Administration: Intravenous
Elesclomol (100 nM) rapidly induces Hsp70 RNA levels with a 4.8-fold increase at 1 hour and a 160-fold increase at 6 hours in Ramos Burkitt's lymphoma B cells in consistent with the intracellular ROS content which increases by 20% as early as 0.5 hour and 385% at 6 hours
Name Type Language
ELESCLOMOL
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
GSK-842879
Code English
STA-4783
Code English
GSK-842879A
Code English
Elesclomol [WHO-DD]
Common Name English
ELESCLOMOL [MI]
Common Name English
ELESCLOMOL [USAN]
Common Name English
ELESCLOMOL [MART.]
Common Name English
STA4783
Code English
elesclomol [INN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 243607
Created by admin on Fri Dec 15 15:41:50 GMT 2023 , Edited by admin on Fri Dec 15 15:41:50 GMT 2023
NCI_THESAURUS C274
Created by admin on Fri Dec 15 15:41:50 GMT 2023 , Edited by admin on Fri Dec 15 15:41:50 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL1972860
Created by admin on Fri Dec 15 15:41:50 GMT 2023 , Edited by admin on Fri Dec 15 15:41:50 GMT 2023
PRIMARY
WIKIPEDIA
ELESCLOMOL
Created by admin on Fri Dec 15 15:41:50 GMT 2023 , Edited by admin on Fri Dec 15 15:41:50 GMT 2023
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CAS
488832-69-5
Created by admin on Fri Dec 15 15:41:50 GMT 2023 , Edited by admin on Fri Dec 15 15:41:50 GMT 2023
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MERCK INDEX
m4866
Created by admin on Fri Dec 15 15:41:50 GMT 2023 , Edited by admin on Fri Dec 15 15:41:50 GMT 2023
PRIMARY Merck Index
FDA UNII
6UK191M53P
Created by admin on Fri Dec 15 15:41:50 GMT 2023 , Edited by admin on Fri Dec 15 15:41:50 GMT 2023
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SMS_ID
100000127739
Created by admin on Fri Dec 15 15:41:50 GMT 2023 , Edited by admin on Fri Dec 15 15:41:50 GMT 2023
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DRUG BANK
DB05719
Created by admin on Fri Dec 15 15:41:50 GMT 2023 , Edited by admin on Fri Dec 15 15:41:50 GMT 2023
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EPA CompTox
DTXSID2042642
Created by admin on Fri Dec 15 15:41:50 GMT 2023 , Edited by admin on Fri Dec 15 15:41:50 GMT 2023
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NCI_THESAURUS
C75291
Created by admin on Fri Dec 15 15:41:50 GMT 2023 , Edited by admin on Fri Dec 15 15:41:50 GMT 2023
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USAN
RR-128
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PUBCHEM
300471
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INN
8762
Created by admin on Fri Dec 15 15:41:50 GMT 2023 , Edited by admin on Fri Dec 15 15:41:50 GMT 2023
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EVMPD
SUB33932
Created by admin on Fri Dec 15 15:41:50 GMT 2023 , Edited by admin on Fri Dec 15 15:41:50 GMT 2023
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MESH
C512195
Created by admin on Fri Dec 15 15:41:50 GMT 2023 , Edited by admin on Fri Dec 15 15:41:50 GMT 2023
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CHEBI
79369
Created by admin on Fri Dec 15 15:41:50 GMT 2023 , Edited by admin on Fri Dec 15 15:41:50 GMT 2023
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