Auranofin

Auranofin
Clinical data


Trade names	Ridaura
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a685038
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	M01CB03 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	40%
Protein binding	60%
Metabolism	Plasma membrane of the cell removes the acetyl groups of the glucose moiety.
Biological half-life	21-31 hours
Excretion	Urine (60%), faeces
Identifiers
IUPAC name Gold(+1) cation; 3,4,5-triacetyloxy-6- (acetyloxymethyl) oxane-2-thiolate; triethylphosphanium
CAS Number	34031-32-8^Y
PubChem CID	6333901
DrugBank	DB00995^Y
ChemSpider	21229878^Y
UNII	3H04W2810V
KEGG	D00237^Y
ChEBI	CHEBI:2922^N
ChEMBL	CHEMBL1366^N
ECHA InfoCard	100.047.077
Chemical and physical data
Formula	C₂₀H₃₅AuO₉PS⁺
Molar mass	679.493 g/mol
3D model (Jmol)	Interactive image
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
^NY (what is this?)

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

Auranofin is used to treat rheumatoid arthritis. It improves arthritis symptoms including painful or tender and swollen joints and morning stiffness. Auranofin is a safer treatment compared to the more common injectable gold thiolates (gold sodium thiomalate and gold thioglucose), but meta-analysis of 66 clinical trials concluded that it is somewhat less effective.

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

Auranofin has been identified in a high-throughput drug screen as 10 times more potent than metronidazole against 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 marked reductions of the number of parasites, the inflammatory reaction to the infestation, and the damage to the liver.

In a cell-based screen, auranofin showed potent activity against replicating and non-replicating M. tuberculosis as well as other gram-positive bacteria. Auranofin protected mice from an otherwise lethal infection with methicillin-resistant S. aureus (MRSA). The drug acts in a similar manner in bacteria as in parasites by inhibiting thioredoxin reductase (TrxR). Studies in humans are needed to evaluate the potential of this drug to treat Gram-positive bacterial infections in humans.

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