Aurothioglucose

Aurothioglucose, is a chemical compound with the formula AuSC₆H₁₁O₅.

Aurothioglucose-2D-skeletal formula

Aurothioglucose-2D-skeletal formula

Clinical use

This gold salt derivative of the sugar glucose was previously used to treat rheumatoid arthritis.

Other names

Aurothioglucose is also known as gold thioglucose or gold salts.

History

As a precious metal, gold was used to cure diseases throughout history, although the efficacy was not established.

Use in rheumatoid arthritis

In 1935, gold drugs were reported to be effective for the treatment of rheumatoid arthritis.<ref name=shaw>Shaw, III C. F.,

 Gold-Based Therapeutic Agents, 
 Chemical Reviews, 
 1999,
 Vol. 99(Issue: 9),
 pp. 2589–600,
 DOI: 10.1021/cr980431o,
 PMID: 11749494,</ref>

Variable results

Although many patients reacted positively to the drug, gold thioglucose was not uniformly effective.
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.<ref name=shaw/> 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 and recrystallized with water and methanol.

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