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
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 was formerly used to treat rheumatoid arthritis.

History[edit]

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 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.

In 2001, aurothoglucose was withdrawn from the Dutch marked, where it had been the only injectable gold preparation available since 1943, forcing hospitals to change medication for a large number of patients to aurothiomalate.[2] The drug had been in use for more than 70 years, and four years later the reasons for its sudden disappearance remained unclear.[3]

Medicinal chemistry[edit]

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)

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.[4] 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. ^ Parenteral gold preparations. Efficacy and safety of therapy after switching from aurothioglucose to aurothiomalate (van Roon et al, J Rheumatol 2005)
  3. ^ An Editorial Is a Golden Opportunity(Alice Klinkhoff, The Journal of Rheumatology 2005) http://www.ncbi.nlm.nih.gov/pubmed/15940754
  4. ^ 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