Aurothioglucose, also known as gold thioglucose, is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

with the formula AuSC₆H₁₁O₅. This derivative of the sugar

glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae d ...

was formerly used to treat

rheumatoid arthritis Rheumatoid arthritis (RA) is a long-term autoimmune disorder that primarily affects synovial joint, joints. It typically results in warm, swollen, and painful joints. Pain and stiffness often worsen following rest. Most commonly, the wrist and h ...

History

Throughout history, gold was used to cure diseases, although the efficacy was not established. In 1935, gold drugs were reported to be effective for the treatment of

. Although many patients reacted positively to the drug, gold thioglucose was not uniformly effective. Only one gold drug remains in active clinical use for this purpose in the United States: auranofin although sodium aurothiomalate (gold sodium thiomalate) and aurothioglucose were still used until recently. In the United Kingdom, only sodium aurothiomalate and auranofin were used recently. In 2001, aurothioglucose was withdrawn from the Dutch market, where it had been the only injectable gold preparation available since 1943, forcing hospitals to change medication for a large number of patients to aurothiomalate. The drug had been in use for more than 70 years, and four years later the reasons for its sudden disappearance remained unclear. It was recently discontinued from the US market along with sodium aurothiomalate leaving only Auranofin as the only gold salt on the US market

Medicinal chemistry

Gold thioglucose features gold in the oxidation state of +I, like other gold thiolates. It is a water-soluble, non-ionic species that is assumed to exist as a polymer. Under physiological conditions, an oxidation-reduction reaction leads to the formation of metallic gold and sulfinic acid derivative of thioglucose. :2 AuSTg → 2 Au + TgSSTg :TgSSTg + H₂O → TgSOH + TgSH :2 TgSOH → TgSO₂H + TgSH :Overall: 2 H₂O + 4 AuSTg → 4 Au + TgSO₂H + 3 TgSH (where AuSTg = gold thioglucose, TgSSTg = thioglucose disulfide, TgSO₂H = sulfinic acid derivative of thioglucose)

Preparation

Gold thioglucose can be prepared by treating gold bromide with thioglucose solution saturated with sulfur dioxide. Gold thioglucose is precipitated with

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

and recrystallized with water and methanol.

Miscellaneous observations

In recent research, it was found that injection of gold thioglucose induces obesity in mice. Aurothioglucose has an interaction with the antimalarial medication hydroxychloroquine.

References

External links