Aurothioglucose

Aurothioglucose

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
Pregnancy cat.	?
Legal status	?
Routes	Intramuscular injection
Pharmacokinetic data
Bioavailability	0%
Identifiers
CAS number	12192-57-3 Y
ATC code	M01CB04
PubChem	CID 6104
ChemSpider	16738764 Y
UNII	2P2V9Q0E78 Y
ChEMBL	CHEMBL1697725 N
Synonyms	Gold thioglucose, Solganal, Auromyose
Chemical data
Formula	C6H11AuO5S
Mol. mass	392.181 g/mol
SMILES	eMolecules & PubChem
InChI 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 Y Key:XHVAWZZCDCWGBK-WYRLRVFGSA-M Y
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

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.

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

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

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.^[2] Aurothioglucose has an interaction with the antimalarial medication hydroxychloroquine.

See also

• Auranofin

References

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