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10-SEPTEMBER-2008 16:47:15 - Aurothioglucose Aurothioglucose Systematic IUPAC name goldI 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. Contents 1 History 2 Medicinal chemistry 3 Preparation 4 Miscellaneous observations 5 See also 6 References 7 External links 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 Auranofin References ^ a b Shaw, III, C. F. 1999. Gold-Based Therapeutic Agents. Chemical Reviews 99: 2589-600. doi:10.1021/cr980431o. ^ 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 v d e Anti-inflammatory and antirheumatic products M01 Anti-inflammatory and antirheumatic products, non-steroids See also: NSAIDs Pyrazolidine/Butylpyrazolidines: · Ampyrone · Clofezone · Kebuzone · Metamizole · Mofebutazone · Oxyphenbutazone · Phenazone · Phenylbutazone · Sulfinpyrazone · Acetic acid derivatives and related substances: · Aceclofenac · Acemetacin · Alclofenac · Bromfenac · Bumadizone · Bufexamac · Diclofenac · Difenpiramide · Etodolac · Fentiazac · Indometacin · Ketorolac · Lonazolac · Oxametacin · Proglumetacin · Sulindac · Tolmetin · Zomepirac · Oxicams: · Ampiroxicam · Droxicam · Lornoxicam · Meloxicam · Piroxicam · Tenoxicam · Propionic acid derivatives: · Alminoprofen · Benoxaprofen · Dexibuprofen · Dexketoprofen · Fenbufen · Fenoprofen · Flunoxaprofen · Flurbiprofen · Ibuprofen · Ibuproxam · Indoprofen · Ketoprofen · Naproxen · Oxaprozin · Pirprofen · Suprofen · Tiaprofenic acid · Fenamates: · Flufenamic acid · Meclofenamic acid · Mefenamic acid · Tolfenamic acid · Coxibs: · Celecoxib · Etoricoxib · Lumiracoxib · Parecoxib · Rofecoxib · Valdecoxib · other anti-inflammatory and antirheumatic agents, non-steroids: · Nabumetone · Niflumic acid · Azapropazone · Glucosamine · Benzydamine · Glycosaminoglycan · Magnesium salicylate · Proquazone · Superoxide dismutase/Orgotein · Nimesulide · Feprazone · Diacerein · Morniflumate · Tenidap · Oxaceprol · Chondroitin sulfate · Specific antirheumatic agents Quinolines: · Oxycinchophen · Gold preparations: · Sodium aurothiomalate · Sodium aurothiosulfate · Auranofin · Aurothioglucose · Aurotioprol · Penicillamine/Bucillamine Tablets This pharmacology-related article is a stub. Retrieved from http://en..org/wiki/Aurothioglucose Categories: Pharmacology stubs | Gold compounds | IARC Group 3 carcinogens | Coordination compounds | Immunosuppressive agents Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Türkçe This page was last modified on 31 May 2008, at 14:24
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