Aurothioglucose

Aurothioglucose

Clinical data
Synonyms	Gold thioglucose, Solganal, Auromyose
Routes of administration	intramuscular injection
ATC code	M01CB04 (WHO)
Pharmacokinetic data
Bioavailability	0%
Identifiers
IUPAC name gold(I) (2S,3S,4R,5S)-3,4,5-trihydroxy- 6-(hydroxymethyl)-oxane-2-thiolate
CAS Number	12192-57-3
PubChem CID	6104
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C6H11AuO5S
Molar mass	392.181 g/mol

WikiDoc Resources for Aurothioglucose
Articles
Most recent articles on Aurothioglucose Most cited articles on Aurothioglucose Review articles on Aurothioglucose Articles on Aurothioglucose in N Eng J Med, Lancet, BMJ
Media
Powerpoint slides on Aurothioglucose Images of Aurothioglucose Photos of Aurothioglucose Podcasts & MP3s on Aurothioglucose Videos on Aurothioglucose
Evidence Based Medicine
Cochrane Collaboration on Aurothioglucose Bandolier on Aurothioglucose TRIP on Aurothioglucose
Clinical Trials
Ongoing Trials on Aurothioglucose at Clinical Trials.gov Trial results on Aurothioglucose Clinical Trials on Aurothioglucose at Google
Guidelines / Policies / Govt
US National Guidelines Clearinghouse on Aurothioglucose NICE Guidance on Aurothioglucose NHS PRODIGY Guidance FDA on Aurothioglucose CDC on Aurothioglucose
Books
Books on Aurothioglucose
News
Aurothioglucose in the news Be alerted to news on Aurothioglucose News trends on Aurothioglucose
Commentary
Blogs on Aurothioglucose
Definitions
Definitions of Aurothioglucose
Patient Resources / Community
Patient resources on Aurothioglucose Discussion groups on Aurothioglucose Patient Handouts on Aurothioglucose Directions to Hospitals Treating Aurothioglucose Risk calculators and risk factors for Aurothioglucose
Healthcare Provider Resources
Symptoms of Aurothioglucose Causes & Risk Factors for Aurothioglucose Diagnostic studies for Aurothioglucose Treatment of Aurothioglucose
Continuing Medical Education (CME)
CME Programs on Aurothioglucose
International
Aurothioglucose en Espanol Aurothioglucose en Francais
Business
Aurothioglucose in the Marketplace Patents on Aurothioglucose
Experimental / Informatics
List of terms related to Aurothioglucose

Overview

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

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. 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.

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. 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.

See also

• Auranofin