Aurothioglucose, also known as gold thioglucose, is a chemical compound

Chemical compound

A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...

 with the formula AuSC₆H₁₁O₅. This derivative of the sugar glucose

Glucose

Glucose is a simple sugar and an important carbohydrate in biology. Cells use it as the primary source of energy and a metabolic intermediate...

 is used to treat rheumatoid arthritis

Rheumatoid arthritis

Rheumatoid arthritis is a chronic, systemic inflammatory disorder that may affect many tissues and organs, but principally attacks synovial joints. The process produces an inflammatory response of the synovium secondary to hyperplasia of synovial cells, excess synovial fluid, and the development...

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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 rheumatoid arthritis. Although many patients reacted positively to the drug, gold thioglucose was not uniformly effective.

Two gold drugs remain in active clinical use for this purpose in the United States: sodium aurothiomalate

Sodium aurothiomalate

Sodium aurothiomalate is a gold compound with the chemical formula C4H4AuNaO4S and is used for its antirheumatic effects to treat rheumatoid arthritis...

 (gold sodium thiomalate) and Aurothioglucose, sold under the trade names Myochrysine and Solgonal, respectively. In the United Kingdom, only sodium aurothiomalate and auranofin

Auranofin

Auranofin is a gold complex classified by the World Health Organization as an antirheumatic agent.It has the brand name Ridaura.-Use in HIV infection:...

 are used.

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 and recrystallized with water and methanol.

Miscellaneous observations

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

Hydroxychloroquine

Hydroxychloroquine is an antimalarial drug, sold under the trade names Plaquenil,Axemal, Dolquine, and Quensyl, also used to reduce inflammation in the treatment of rheumatoid arthritis and lupus...

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