Aurothioglucose

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Aurothioglucose
Authioglucose.png
Aurothioglucose-3D-vdW.png
Systematic (IUPAC) name
gold(I) (2S,3S,4R,5S)-3,4,5-trihydroxy-
6-(hydroxymethyl)-oxane-2-thiolate
Clinical data
AHFS/Drugs.com Consumer Drug Information
MedlinePlus a600032
Legal status ?
Routes Intramuscular injection
Pharmacokinetic data
Bioavailability 0%
Identifiers
CAS number 12192-57-3 YesY
ATC code M01CB04
PubChem CID 6104
ChemSpider 16738764 YesY
UNII 2P2V9Q0E78 YesY
ChEMBL CHEMBL1697725 N
Synonyms Gold thioglucose, Solganal, Auromyose
Chemical data
Formula C6H11AuO5S 
Mol. mass 392.181 g/mol
 N (what is this?)  (verify)

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.

History[edit]

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 rheumatoid arthritis.[1] Although many patients reacted positively to the drug, gold thioglucose was not uniformly effective.

Three gold drugs remain in active clinical use for this purpose in the United States: auranofin, sodium aurothiomalate (gold sodium thiomalate) and aurothioglucose. In the United Kingdom, only sodium aurothiomalate and auranofin are used.

Medicinal chemistry[edit]

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]

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[edit]

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

See also[edit]

References[edit]

  1. ^ a b Shaw, III, C. F. (1999). "Gold-Based Therapeutic Agents". Chemical Reviews 99 (9): 2589–600. doi:10.1021/cr980431o. PMID 11749494. 
  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. 

External links[edit]

Media related to Aurothioglucose at Wikimedia Commons