Antiarthritic Auranofin

Razi, M.T, Sadler, P.J., Hill, D.T. and Sutton, B.M. (1983) Proton, carbon-13, and phosphoms-31 nudear magnetic resonance studies of (2,3,4,6-tetra-O-acetyl-l-thio-p -n-glucopyranosato-S) (triethylphosphine)gold (auranofin), a novel antiarthritic agent Journal of the Chemical Society, Dalton Transactions, (7), 1331-1334. 

Thiolate ligands also afford an interesting variety of species [156-161]. Because or their relation with the antiarthritic drug Auranofin, thiolate-goldphosphine derivatives have received great interest. The simplest structures are those in which the thiolate bridges two gold atoms and thus different compounds of stoichiometry... 

FIGURE 16-21 Gold Antiarthritic Drugs, (a) Sodium aurothioraalate. (b) Aurothioglucose. (c) Auranofin. 

Auranofin, a unique gold compound, has heen available for clinical use for 25 years after it proved to be one of the most potent oral antiarthritic com-... 

We reported previously on a series of phosphine gold coordination compounds that produced antiarthritic activity in adjuvant induced arthritis in rats when administered by the oral route (32) All other gold compounds are effective only when administered parenterally One member from this group, (2,3,4,6 tetra-0-acetyl l-thio-3-D-glucopyranosato-S ) (triethylphosphine)gold, auranofin (jj, exhibited potent activity of this type and is now undergoing clinical trial ... 

FIGURE 27 Auranofin, a gold salt with antiarthritic properties, reduces inflammation by altering the immune system. 

The nature of the phosphine ligand (R3P) influenced the extent of oral absorption of the complex and antiarthritic activity was found to be closely related to the gold serum concentrations (Fig. 3). The maximum absorption and activity occurred when the phosphine was EtsP. EtaPAuCl was initially selected for clinical trial but diarrhoea proved to be a troublesome side-effect and it was abandoned in favour of the tetraacetylated thioglucose derivative, auranofin (9). Under the tradename Ridaura this was approved by the FDA for clinical use in the USA in May 1985. 

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