Auranofin

Specifications / Handling

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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

Product-specific References

Description

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

Auranofin. New oral gold compound for treatment of rheumatoid arthritis: A.E. Finkelstein, et al.; Ann. Rheum. Dis. 35, 251 (1976)
Inhibition of alveolar macrophage 5-lipoxygenase metabolism by auranofin: M. Peters-Golden & C. Shelly; Biochem. Pharmacol. 38, 1589 (1989)
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)
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)
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)
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)
The biological activity of auranofin: implications for novel treatment of diseases: J.M. Madeira, et al.; Inflammopharmacology 20, 297 (2012) (Review)
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)
Drug repositioning: auranofin as a prospective antimicrobial agent for the treatment of severe staphylococcal infections: M.I. Cassetta, et al.; Biometals 27, 787 (2014)
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)
Clinically used antirheumatic agent auranofin is a proteasomal deubiquitinase inhibitor and inhibits tumor growth: M. Liu, et al.; Oncotarget 5, 5453 (2014)
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)
Auranofin: repurposing an old drug for a golden new age: C. Roder & M.J. Thomson; Drugs R.D. 15, 13 (2015) (Review)
Auranofin exerts broad-spectrum bactericidal activities by targeting thiol-redox homeostasis: M.B. Harbut, et al.; PNAS 112, 4453 (2015)
Mercury binding to proteins disclosed by ESI MS experiments: The case of three organomercurials: A. Geri, et al.; J. Inorg. Biochem. 252, 112479 (2024)

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