Aurothioglucose

  1. Home
  2. Wiki

Aurothioglucose
Clinical data
Other namesGold thioglucose, Solganal, Auromyose
AHFS/Drugs.comConsumer Drug Information
Routes of
administration		Intramuscular injection
ATC code
Pharmacokinetic data
Bioavailability0%
Identifiers
  • gold(I) (2S,3S,4R,5S)-3,4,5-trihydroxy-
    6-(hydroxymethyl)-oxane-2-thiolate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.032.138 Edit this at Wikidata
Chemical and physical data
FormulaC6H11AuO5S
Molar mass392.18 g·mol−1
3D model (JSmol)
  • O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1S[Au]
  • InChI=1S/C6H12O5S.Au/c7-1-2-3(8)4(9)5(10)6(12)11-2;/h2-10,12H,1H2;/q;+1/p-1/t2-,3-,4+,5-,6-;/m1./s1 checkY
  • Key:XHVAWZZCDCWGBK-WYRLRVFGSA-M checkY
 ☒NcheckY (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.[1]

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

Only one gold drug remains in active clinical use for this purpose in the United States: auranofin, sodium aurothiomalate (gold sodium thiomalate) and aurothioglucose were discontinued by their manufacturers in 2019 due to gold shortages, and the rising cost of gold.[3][4]

In 2001, aurothioglucose was withdrawn from the Dutch market, where it had been the only injectable gold preparation available since 1943, forcing hospitals to change medication for a large number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.[5] The drug had been in use for more than 70 years, and four years later the reasons for its sudden disappearance remained unclear.[6]

It was discontinued from the US market in 2019, along with sodium aurothiomalate,[7] leaving only generic Auranofin as the only gold salt on the US market.[3][8]

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.[2] Under physiological conditions, an oxidation-reduction reaction leads to the formation of metallic gold and sulfinic acid derivative of thioglucose.[1]

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 induces obesity in mice.[9] Aurothioglucose has an interaction with the antimalarial medication hydroxychloroquine.[1]

See also

[edit]

References

[edit]
  1. ^ a b c Minigh J (2008). Enna SJ, Bylund DB (eds.). "Aurothioglucose". Xpharm: the Comprehensive Pharmacology Reference. Elsevier Inc.: 1–5. doi:10.1016/B978-008055232-3.61269-3. ISBN 978-0-08-055232-3. Retrieved 28 August 2025.
  2. ^ a b Shaw III CF (September 1999). "Gold-based therapeutic agents". Chemical Reviews. 99 (9). ACS Publications: 2589–2600. doi:10.1021/cr980431o. PMID 11749494.
  3. ^ a b Papich MG (2021). "Aurothioglucose". Papich Handbook of Veterinary Drugs. Fifth Edition: 72–73. doi:10.1016/B978-0-323-70957-6.00043-1. ISBN 978-0-323-70957-6. Retrieved 28 August 2025.
  4. ^ "Myocrisin (Sodium aurothiomalate) injection: Permanent discontinuation end of supply in 2019" (PDF). Sanofi. Aventis Pharma Ltd. 10 June 2019. Retrieved 28 August 2025.
  5. ^ van Roon EN, van de Laar MA, Janssen M, Kruijsen MW, Jansen TL, Brouwers JR (June 2005). "Parenteral gold preparations. Efficacy and safety of therapy after switching from aurothioglucose to aurothiomalate". The Journal of Rheumatology. 32 (6): 1026–1030. PMID 15940762.
  6. ^ Klinkhoff A (June 2005). "An editorial is a golden opportunity". The Journal of Rheumatology. 32 (6): 978–979. PMID 15940754.
  7. ^ "Myocrisin permanent discontinuation". Letters and drug alerts sent to healthcare professionals in June 2019. © Crown of the United Kingdom. 17 July 2019. Retrieved 28 August 2025.
  8. ^ Stanway JA, Walker D (4 January 2022). "Inflammatory arthritis-the end of the golden age". Rheumatology Advances in Practice. 6 (1). British Society for Rheumatology: rkac015. doi:10.1093/rap/rkac015. PMC 8902173. PMID 35265790.{{cite journal}}: CS1 maint: article number as page number (link)
  9. ^ Naruta E, Buko V (October 2001). "Hypolipidemic effect of pantothenic acid derivatives in mice with hypothalamic obesity induced by aurothioglucose". Experimental and Toxicologic Pathology. 53 (5): 393–398. doi:10.1078/0940-2993-00205. PMID 11817109.
[edit]

Media related to Aurothioglucose at Wikimedia Commons