Aurothioglucose

	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

Aurothioglucose
Clinical data
Synonyms	Gold thioglucose, Solganal, Auromyose
AHFS/Drugs.com	Consumer Drug Information
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;
ChemSpider	16738764 ;
UNII	2P2V9Q0E78;
ChEMBL	ChEMBL1697725 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C6H11AuO5S
Molar mass	392.181 g/mol
3D model (JSmol)	Interactive image;
	SMILES O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1S[Au];
	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 ; Key:XHVAWZZCDCWGBK-WYRLRVFGSA-M ;
(what is this?) (verify)

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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

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

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 was found that injection of gold thioglucose in the mouse induces obesity.^[4] Aurothioglucose has an interaction with the antimalarial medication hydroxychloroquine.

References

↑ ^1.0 ^1.1 Shaw, III, C. F. (1999). "Gold-Based Therapeutic Agents". Chemical Reviews. 99 (9): 2589–600. doi:10.1021/cr980431o. PMID 11749494.
↑ Parenteral gold preparations. Efficacy and safety of therapy after switching from aurothioglucose to aurothiomalate (van Roon et al, J Rheumatol 2005)
↑ PMID 15940754 (PMID 15940754)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
↑ 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.

[shaw-1] 1.0 ^1.1 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] PMID 15940754 (PMID 15940754)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand

[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.

[1]

[2]

[3]

[4]