Tetrathiomolybdate
PubChem CID
5245480
Structure
Molecular Formula
Synonyms
- Tetrathiomolybdate
- Thiomolybdate
- 16330-92-0
- Tiomolibdate ion
- Tetrathioxomolybdate(2-)
Molecular Weight
226.2 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Component Compounds
Dates
- Create:2004-09-16
- Modify:2025-01-18
Description
Tetrathiomolybdate(2-) is a molybdenum coordination entity. It has a role as a copper chelator.
Tetrathiomolybdate is an oral, small-molecule, anticopper agent that is highly specific for lowering the levels of free copper in serum. COPREXA has completed pivotal clinical trials for the treatment of neurologic Wilson's disease. It is also developed for fibrotic disorders based upon the rationale that the fibrotic disease process is dependent upon the availability of free copper in the body.
Tetrathiomolybdate is an orally bioavailable metal copper (Cu) chelator, with potential antiangiogenic, anti-metastatic and antitumor activities. Upon oral administration, tetrathiomolybdate (TM) targets and binds to copper and food protein in the gastrointestinal (GI) tract, thereby forming stable complexes and preventing copper uptake and reabsorption. Additionally, absorbed free TM targets and binds to copper and serum albumin in the bloodstream. This depletes systemic copper reserves and deprives the tumor microenvironment (TME) from copper. Chelation of copper by TM downregulates the expression of angiogenic factors of which copper is a cofactor, such as vascular endothelial growth factor (VEGF) and basic fibroblast growth factor (bFGF), and prevents the production of nuclear factor-kappa B (NF-kB). Copper deprivation also inhibits the activity and levels of copper-dependent angiogenic enzymes, such as vascular endothelial growth factor receptor (VEGFR). This modulates the activity of VEGFR-positive endothelial progenitor cells (EPCs) that are necessary for metastasis. EPC deficiency results in the inhibition of angiogenesis and prevents metastasis. TM also inhibits the activities of other copper-containing metalloenzymes, including superoxide dismutase 1 (SOD1) in endothelial cells, cytochrome C oxidase, vascular adhesion protein-1 (VAP-1), antioxidant 1 copper chaperone (ATOX-1) and matrix metalloproteinase 9 (MMP-9). Inhibition of these enzymes interferes with the activation of several signal transduction pathways required for cellular proliferation and angiogenesis. TM also inhibits the activity and levels of lysyl oxidase-like 2 (LOXL2; lysyl oxidase homolog 2), a copper dependent amine oxidase that is critical for modeling the pre-metastatic niche and promotes metastasis, tumor cell migration and invasiveness. In addition, copper depletion also attenuates the activation of host cells within the tumor microenvironment including cancer-associated fibroblasts (CAFs), modulates tumor associated macrophages (TAMs) and promotes cytotoxic T-lymphocyte (CTL)-mediated anti-tumor immune responses.
Chemical Structure Depiction
Conformer generation is disallowed since MMFF94s unsupported element, mixture or salt
bis(sulfanylidene)molybdenum;sulfanide
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/Mo.2H2S.2S/h;2*1H2;;/p-2
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
VVRHUOPINLMZBL-UHFFFAOYSA-L
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
[SH-].[SH-].S=[Mo]=S
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
H2MoS4-2
Computed by PubChem 2.2 (PubChem release 2021.10.14)
16330-92-0
18198-15-7 (di-hydrochloride salt)
- ammonium tetrathiomolybdate
- ATN-224
- tetrathiomolybdate
- tetrathiomolybdate bis-choline salt
- tetrathiomolybdate, dipotassium salt
- tetrathiomolybdate, disodium salt
- thiomolybdate
- TTM cpd
- Tetrathiomolybdate
- Thiomolybdate
- 16330-92-0
- Tiomolibdate ion
- Tetrathioxomolybdate(2-)
- Molybdate(2-), tetrathioxo-, (T-4)-
- tetrathiomolybdate(2-)
- 91U3TGV99T
- bis(sulfanylidene)molybdenum;sulfanide
- UNII-91U3TGV99T
- CCRIS 9412
- CHEBI:30703
- Tetrathiomolybdate ion
- Tetrathiomolybdate 2-ion
- tetrasulfidomolybdate(VI)
- Thiomolybdate (mos42-)
- tetrasulfidomolybdate(2-)
- disulfido(dithioxo)molybdenum
- Tetrathiomolybdate (mos42-)
- Molybdenum sulfide (mos42-)
- (T-4)-tetrathioxomolybdate(2-)
- [MoS4](2-)
- DB05088
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
226.2 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
227.809338 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
227.809338 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
66.2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
5
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
-2
Reference
Computed by PubChem
Property Name
Complexity
Property Value
19.1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
3
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
300 °C with decomposition
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Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
Investigated for use/treatment in liver disease and pulmonary fibrosis.
Tetrathiomolybdate demonstrated the ability to reduce toxic free copper levels and substantially improve clinical neurologic outcomes in Wilson’s patients. Studies also showed it is capable of specifically inhibiting chronic fibrotic disease processes in the lung.
Angiogenesis Inhibitors
Agents and endogenous substances that antagonize or inhibit the development of new blood vessels. (See all compounds classified as Angiogenesis Inhibitors.)
Chelating Agents
Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS. (See all compounds classified as Chelating Agents.)
Enzyme Inhibitors
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)
Tetrathiomolybdate has demonstrated the ability to inhibit fibrosis in a number of well established animal models through the sequestration of available copper and inhibition of key fibrotric cytokines, including secreted protein acid rich in cysteine (SPARC), NFkappaB, TGF-beta, FGF-2, IL-1, IL-6, IL-8, and connective tissue growth factor (CTGF).
- ChEBITetrathiomolybdate(2-)https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:30703
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useTetrathiomolybdatehttps://www.drugbank.ca/drugs/DB05088
- NCI Thesaurus (NCIt)LICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuseNCI Thesaurushttps://ncit.nci.nih.gov
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linkingTIOMOLIBDATE IONhttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/91U3TGV99T
- ClinicalTrials.govLICENSEThe ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
- Comparative Toxicogenomics Database (CTD)LICENSEIt is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.http://ctdbase.org/about/legal.jsptetrathiomolybdatehttps://ctdbase.org/detail.go?type=chem&acc=C020809
- Therapeutic Target Database (TTD)
- European Chemicals Agency (ECHA)LICENSEUse of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.https://echa.europa.eu/web/guest/legal-noticeTetrathiomolybdatehttps://echa.europa.eu/substance-information/-/substanceinfo/100.128.153
- Protein Data Bank in Europe (PDBe)
- Wikidatatetrathiomolybdatehttps://www.wikidata.org/wiki/Q21396219
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmltetrathiomolybdatehttps://www.ncbi.nlm.nih.gov/mesh/67020809Angiogenesis Inhibitorshttps://www.ncbi.nlm.nih.gov/mesh/68020533Chelating Agentshttps://www.ncbi.nlm.nih.gov/mesh/68002614Enzyme Inhibitorshttps://www.ncbi.nlm.nih.gov/mesh/68004791
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
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