Auranofin

CHF 65.00
In stock
AG-CR1-3611-M02525 mgCHF 65.00
AG-CR1-3611-M100100 mgCHF 100.00
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Product Details
Synonyms 1-Thio-β-D-glucopyranosatotriethylphosphine gold-2,3,4,6-tetra- acetate; NSC 321521; SKF 39162; Triethylphosphine gold
Product Type Chemical
Properties
Formula

C20H34AuO9PS

MW 678.5
Merck Index 14: 878
CAS 34031-32-8
RTECS MD6500000
Purity Chemicals ≥95%
Appearance White to off-white solid.
Solubility Soluble in DMSO or 100% ethanol. Insoluble in water.
Identity Determined by 1H-NMR.
InChi Key AUJRCFUBUPVWSZ-XTZHGVARSA-M
Smiles CCP(CC)(CC)=[Au]SC1OC(COC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Protect from light.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • Anti-inflammatory and anti-arthritic agent. Represses the activation of the NLRP3/IL-1β pathway.
  • Inhibitor of 5-lipoxygenase in human neutrophils, IKB kinase (IKK) by modifying Cys-179 of the IKKβ subunit 5.
  • Potent thioredoxin reductase (TrxR) inhibitor. Induces mitochondrial membrane permeability transition.
  • Anti-cancer compound with anti-proliferative activity. Shown to induce apoptosis and necrosis.
  • STAT3 and telomerase activity inhibitor.
  • Proteasomal deubiquitinase inhibitor.
  • Antibiotic, antiviral and antiparasitic compound.
  • Immunosuppressive.
Product References
  1. Auranofin. New oral gold compound for treatment of rheumatoid arthritis: A.E. Finkelstein, et al.; Ann. Rheum. Dis. 35, 251 (1976)
  2. Inhibition of alveolar macrophage 5-lipoxygenase metabolism by auranofin: M. Peters-Golden & C. Shelly; Biochem. Pharmacol. 38, 1589 (1989)
  3. Gold compound auranofin inhibits IkappaB kinase (IKK) by modifying Cys-179 of IKKbeta subunit: K.I. Jeon, et al.; Exp. Mol. Med. 35, 61 (2003)
  4. Inhibition of thioredoxin reductase by auranofin induces apoptosis in cisplatin-resistant human ovarian cancer cells: C. Marzano, et al.; Free Radic. Biol. Med. 42, 872 (2007)
  5. Auranofin, an immunosuppressive drug, inhibits MHC class I and MHC class II pathways of antigen presentation in dendritic cells: S. Han, et al.; Arch. Pharm. Res. 31, 370 (2008)
  6. The gold compound auranofin induces apoptosis of human multiple myeloma cells through both down-regulation of STAT3 and inhibition of NF-κB activity: A. Nakaya, et al.; Leuk. Res. 35, 243 (2011)
  7. The biological activity of auranofin: implications for novel treatment of diseases: J.M. Madeira, et al.; Inflammopharmacology 20, 297 (2012) (Review)
  8. Antiproliferative effect of gold(I) compound auranofin through inhibition of STAT3 and telomerase activity in MDA-MB 231 human breast cancer cells: N.H. Kim, et al.; BMB Rep. 46, 59 (2013)
  9. Drug repositioning: auranofin as a prospective antimicrobial agent for the treatment of severe staphylococcal infections: M.I. Cassetta, et al.; Biometals 27, 787 (2014)
  10. Suppression of the pro-inflammatory NLRP3/interleukin-1β pathway in macrophages by the thioredoxin reductase inhibitor auranofin: E. Isakov, et al.; Biochim. Biophys. Acta 1840, 3153 (2014)
  11. Clinically used antirheumatic agent auranofin is a proteasomal deubiquitinase inhibitor and inhibits tumor growth: M. Liu, et al.; Oncotarget 5, 5453 (2014)
  12. Auranofin induces apoptosis and necrosis in HeLa cells via oxidative stress and glutathione depletion: B.R. You, et al.; Mol. Med. Rep. 11, 1428 (2015)
  13. Auranofin: repurposing an old drug for a golden new age: C. Roder & M.J. Thomson; Drugs R.D. 15, 13 (2015) (Review)
  14. Auranofin exerts broad-spectrum bactericidal activities by targeting thiol-redox homeostasis: M.B. Harbut, et al.; PNAS 112, 4453 (2015)
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