Auranofin

Auranofin

Systematic (IUPAC) name
gold(+1) cation; 3,4,5-triacetyloxy-6- (acetyloxymethyl) oxane-2-thiolate; triethylphosphanium
Clinical data
Trade names	Ridaura
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a685038
Pregnancy cat.	C (US)
Legal status	℞-only (US)
Routes	Oral
Identifiers
CAS number	34031-32-8 Y
ATC code	M01CB03
PubChem	CID 6333901
DrugBank	DB00995
ChemSpider	21229878 Y
UNII	3H04W2810V Y
KEGG	D00237 Y
ChEBI	CHEBI:2922 N
ChEMBL	CHEMBL1366 N
Chemical data
Formula	C20H35AuO9PS+
Mol. mass	679.493 g/mol
SMILES CC(=O)O[C@H]1O[C@@H](S[Au]P(CC)(CC)CC)[C@H](OC(C)=O)[C@@H](OC(C)=O)C1OC(C)=O
InChI InChI=1S/C13H18O9S.C6H15P.Au/c1-5(14)18-9-10(19-6(2)15)12(21-8(4)17)22-13(23)11(9)20-7(3)16;1-4-7(5-2)6-3;/h9-13,23H,1-4H3;4-6H2,1-3H3;/t9-,10?,11+,12-,13-;;/m0../s1 Y Key:JCUNAWURTWIACY-YHEXQHTOSA-N Y
N (what is this?)  (verify)

Auranofin is a gold complex classified by the World Health Organization as an antirheumatic agent. It has the brand name Ridaura.

Use

Auranofin is used to treat rheumatoid arthritis. It improves arthritis symptoms including painful or tender and swollen joints and morning stiffness.

Research

HIV infection

Auranofin is under investigation as means of reducing the viral reservoir of HIV that lies latent in the body's T-cells despite treatment with antiretroviral therapy.

Amebiasis

Auranofin has been identified in a high-throughput drug screen as 10 times more potent than metronidazole on Entamoeba histolytica, the protozoan agent of human amebiasis. Assays of thioredoxin reductase and transcriptional profiling suggest that the effect of auranofin on the enzyme enhances the sensitivity of the trophozoites to reactive oxygen-mediated killing in mouse and hamster models; the results are markedly reductions of the number of parasites, the inflammatory reaction to the infestation and the damage to the liver.

Further reading

• Jeon K, Byun M, Jue D (2003). "Gold compound auranofin inhibits IkappaB kinase (IKK) by modifying Cys-179 of IKKbeta subunit". Exp Mol Med 35 (2): 61–6. PMID 12754408. 
• Kim I, Jin J, Lee I, Park S (2004). "Auranofin induces apoptosis and when combined with retinoic acid enhances differentiation of acute promyelocytic leukaemia cells in vitro". Br J Pharmacol 142 (4): 749–55. doi:10.1038/sj.bjp.0705708. PMC 1575039. PMID 15159275. 
• Venardos K, Harrison G, Headrick J, Perkins A (2004). "Auranofin increases apoptosis and ischaemia-reperfusion injury in the rat isolated heart". Clin Exp Pharmacol Physiol 31 (5–6): 289–94. doi:10.1111/j.1440-1681.2004.03993.x. PMID 15191400. 
• Hafejee A, Winhoven S, Coulson I (2004). "Jessner's lymphocytic infiltrate responding to oral auranofin". J Dermatolog Treat 15 (5): 331–2. doi:10.1080/09546630410016924. PMID 15370403. 
• Rigobello M, Folda A, Baldoin M, Scutari G, Bindoli A (2005). "Effect of auranofin on the mitochondrial generation of hydrogen peroxide. Role of thioredoxin reductase". Free Radic Res 39 (7): 687–95. doi:10.1080/10715760500135391. PMID 16036347. 
• Suarez-Almazor ME, Spooner CH, Belseck E, Shea B (2000). "Auranofin versus placebo in rheumatoid arthritis". In Suarez-Almazor, Maria E. Cochrane Database Syst Rev (2): CD002048. doi:10.1002/14651858.CD002048. PMID 10796461. 

External links

• MedlinePlus DrugInfo medmaster-a685038