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Aurothioglucose



Aurothioglucose
Systematic (IUPAC) name
gold(I) (2S,3S,4R,5S)-3,4,5-trihydroxy-
6-(hydroxymethyl)-oxane-2-thiolate
Identifiers
CAS number 12192-57-3
ATC code M01CB04
PubChem 6104
Chemical data
Formula C6H11AuO5S 
Mol. mass 392.181 g/mol
Synonyms Gold thioglucose, Solganal, Auromyose
Pharmacokinetic data
Bioavailability 0%
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?

Legal status
Routes intramuscular injection

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.

Additional recommended knowledge

Contents

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.[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

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

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

References

  1. ^ a b Shaw, III, C. F. (1999). "Gold-Based Therapeutic Agents". Chemical Reviews 99: 2589-600. doi:10.1021/cr980431o.
  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. PMID 11817109.

Acetic acid derivatives and related substances (Indometacin, Sulindac, Tolmetin, Zomepirac, Diclofenac, Alclofenac, Bumadizone, Etodolac, Lonazolac, Fentiazac, Acemetacin, Difenpiramide, Oxametacin, Proglumetacin, Ketorolac, Aceclofenac, Bufexamac)

Oxicams (Piroxicam, Tenoxicam, Droxicam, Lornoxicam, Meloxicam)

Propionic acid derivatives (Ibuprofen, Naproxen, Ketoprofen, Fenoprofen, Fenbufen, Benoxaprofen, Suprofen, Pirprofen, Flurbiprofen, Indoprofen, Tiaprofenic acid, Oxaprozin, Ibuproxam, Dexibuprofen, Flunoxaprofen, Alminoprofen, Dexketoprofen)

Fenamates (Mefenamic acid, Tolfenamic acid, Flufenamic acid, Meclofenamic acid)

Coxibs (Celecoxib, Rofecoxib, Valdecoxib, Parecoxib, Etoricoxib, Lumiracoxib)

other anti-inflammatory and antirheumatic agents, non-steroids (Nabumetone, Niflumic acid, Azapropazone, Glucosamine, Benzydamine, Glucosaminoglycan polysulfate, Proquazone, Orgotein, Nimesulide, Feprazone, Diacerein, Morniflumate, Tenidap, Oxaceprol, Chondroitin sulfate)
Specific antirheumatic agentsQuinolines (Oxycinchophen) - Gold preparations (Sodium aurothiomalate, Sodium aurothiosulfate, Auranofin, Aurothioglucose, Aurotioprol) - Penicillamine/Bucillamine
  This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Aurothioglucose". A list of authors is available in Wikipedia.
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