Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Elesclomol
- DrugBank Accession Number
- DB05719
- Background
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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Elesclomol (DB05719)
- Weight
- Average: 400.518
Monoisotopic: 400.102767284 - Chemical Formula
- C19H20N4O2S2
- Synonyms
- 1-N'-Benzenecarbothioyl-3-(2-benzenecarbothioyl-2-methylhydrazinyl)-N'-methyl-oxopropanehydrazidide
- Elesclomol
- Élesclomol
- Elesclomolum
- External IDs
- GSK-842879
- GSK-842879A
- STA-4783
Pharmacology
- Indication
Investigated for use/treatment in melanoma.
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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.
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Not Available
- Direct Parent
- Benzene and substituted derivatives
- Alternative Parents
- 1,3-dicarbonyl compounds / Thioamides / Carboxylic acid hydrazides / Thiocarbonyl compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1,3-dicarbonyl compound / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid hydrazide / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxide / Organic oxygen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- carbohydrazide, thiocarbonyl compound (CHEBI:79369)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 6UK191M53P
- CAS number
- 488832-69-5
- InChI Key
- BKJIXTWSNXCKJH-UHFFFAOYSA-N
- 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)
- IUPAC Name
- N'1,N'3-dibenzenecarbothioyl-N'1,N'3-dimethylpropanedihydrazide
- SMILES
- CN(NC(=O)CC(=O)NN(C)C(=S)C1=CC=CC=C1)C(=S)C1=CC=CC=C1
References
- General References
- Gehrmann M: Drug evaluation: STA-4783--enhancing taxane efficacy by induction of Hsp70. Curr Opin Investig Drugs. 2006 Jun;7(6):574-80. [Article]
- Berkenblit A, Eder JP Jr, Ryan DP, Seiden MV, Tatsuta N, Sherman ML, Dahl TA, Dezube BJ, Supko JG: Phase I clinical trial of STA-4783 in combination with paclitaxel in patients with refractory solid tumors. Clin Cancer Res. 2007 Jan 15;13(2 Pt 1):584-90. [Article]
- External Links
- KEGG Drug
- D08909
- PubChem Compound
- 300471
- PubChem Substance
- 175427028
- ChemSpider
- 265501
- ChEBI
- 79369
- ChEMBL
- CHEMBL1972860
- ZINC
- ZINC000001716098
- Wikipedia
- Elesclomol
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00282 mg/mL ALOGPS logP 2.34 ALOGPS logP 2.81 Chemaxon logS -5.2 ALOGPS pKa (Strongest Acidic) 10.9 Chemaxon pKa (Strongest Basic) -8.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 64.68 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 115.48 m3·mol-1 Chemaxon Polarizability 41.29 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7792 Blood Brain Barrier + 0.9556 Caco-2 permeable - 0.5273 P-glycoprotein substrate Non-substrate 0.8186 P-glycoprotein inhibitor I Non-inhibitor 0.6672 P-glycoprotein inhibitor II Non-inhibitor 0.9597 Renal organic cation transporter Non-inhibitor 0.9014 CYP450 2C9 substrate Non-substrate 0.6508 CYP450 2D6 substrate Non-substrate 0.8242 CYP450 3A4 substrate Non-substrate 0.5524 CYP450 1A2 substrate Non-inhibitor 0.6271 CYP450 2C9 inhibitor Non-inhibitor 0.601 CYP450 2D6 inhibitor Non-inhibitor 0.9158 CYP450 2C19 inhibitor Non-inhibitor 0.6511 CYP450 3A4 inhibitor Non-inhibitor 0.5964 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6067 Ames test Non AMES toxic 0.6926 Carcinogenicity Non-carcinogens 0.5242 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.3817 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9753 hERG inhibition (predictor II) Non-inhibitor 0.7308
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00di-0921000000-b8ea4f073a5ad5d4a8fa Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0uk9-0600900000-b6d9f138711aff72ffbd Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0129000000-1d159b01e434729a20e1 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0900000000-d320593c586af479e3ab Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-06fu-4921000000-7326e56933ce44927643 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-1900000000-87b889a497525bc768bf Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-5900000000-42babc08e2b77b90ef72 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 205.5750798 predictedDarkChem Lite v0.1.0 [M-H]- 181.94038 predictedDeepCCS 1.0 (2019) [M+H]+ 205.9044798 predictedDarkChem Lite v0.1.0 [M+H]+ 184.29839 predictedDeepCCS 1.0 (2019) [M+Na]+ 205.2880798 predictedDarkChem Lite v0.1.0 [M+Na]+ 191.31746 predictedDeepCCS 1.0 (2019)
Drug created at November 18, 2007 18:27 / Updated at January 14, 2023 19:03