Aurothioglucose

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Aurothioglucose
Systematic (IUPAC) name
gold(I) (2S,3S,4R,5S)-3,4,5-trihydroxy-
6-(hydroxymethyl)-oxane-2-thiolate
Identifiers
CAS number 12192-57-3
ATC code M01CB04
PubChem 6104
Chemical data
Formula C6H11AuO5S 
Mol. mass 392.181 g/mol
Synonyms Gold thioglucose, Solganal, Auromyose
Pharmacokinetic data
Bioavailability 0%
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?

Legal status
Routes intramuscular injection

Aurothioglucose, also known as gold thioglucose, is a chemical compound with the formula AuSC6H11O5. This derivative of the sugar glucose is used to treat rheumatoid arthritis.

Contents

[edit] History

Main article: Gold salts

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

[edit] Medicinal chemistry

Main article: gold

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)

[edit] 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.

[edit] Miscellaneous observations

In recent research, it has found that injection of gold thioglucose in the mouse induces obesity.[2] Aurothioglucose has an interaction with the antimalarial medication Hydroxychloroquine.

[edit] See also

[edit] References

  1. ^ a b Shaw, III, C. F. (1999). "Gold-Based Therapeutic Agents". Chemical Reviews 99: 2589–600. doi:10.1021/cr980431o. 
  2. ^ Naruta E, Buko V (2001). "Hypolipidemic effect of pantothenic acid derivatives in mice with hypothalamic obesity induced by aurothioglucose.". Exp Toxicol Pathol 53 (5): 393–8. doi:10.1078/0940-2993-00205. PMID 11817109. 

[edit] External links