Aurothioglucose
Aurothioglucose, is a chemical compound with the formula AuSC6H11O5.
Clinical use[edit | edit source]
This gold salt derivative of the sugar glucose was previously used to treat rheumatoid arthritis.
Other names[edit | edit source]
Aurothioglucose is also known as gold thioglucose or gold salts.
History[edit | edit source]
As a precious metal, gold was used to cure diseases throughout history, although the efficacy was not established.
Use in rheumatoid arthritis[edit | edit source]
In 1935, gold drugs were reported to be effective for the treatment of rheumatoid arthritis.[1]
Variable results[edit | edit source]
- 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[edit | edit source]
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.[1] 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[edit | edit source]
- 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.
See also[edit | edit source]
Portions of content adapted from Wikipedia's article on Aurothioglucose which is released under the CC BY-SA 3.0.
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