Aurothioglucose
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Aurothioglucose
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| Systematic (IUPAC) name | |
| gold(I) (2S,3S,4R,5S)-3,4,5-trihydroxy- 6-(hydroxymethyl)-oxane-2-thiolate |
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| Identifiers | |
| CAS number | 12192-57-3 |
| ATC code | M01CB04 |
| PubChem | 6104 |
| Chemical data | |
| Formula | C6H11AuO5S |
| Mol. weight | 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 (gold thioglucose) is an organogold compound used for its antirheumatic effects to treat rheumatoid arthritis. In recent research, it has found that injection of gold thioglucose in the mouse induces obesity.[1]
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[edit] History
Throughout ancient history, gold was used as medicine to cure diseases. Sometimes, it was used to ward off disease and evil spirits in the form of amulets and pendants. In many times, gold powders were administered to ill persons. After alchemists learned how to dissolve gold, pure gold was produced and also used as medicine. In modern age, gold drugs are used to treat rheumatoid arthritis. Although many patients reacted positively to the drug, gold thioglucose was not effecitve for all patients.
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.[2] In the United Kingdom only sodium aurothiomalate and auranofin are used.
[edit] Chemistry
Compounds of gold can have oxidation states ranging from -I to +V. Gold(I) and gold(III) have extensive chemistries in aqueous system and biological system. Gold in Gold thioglucose has an oxidation state of +I. Gold(I) has closed-shell configuration with ten electrons in d orbital and has three principal coordination geometries: linear, trigonal, and tetrahedral.
Gold thioglucose is a water-soluble, nonionizable compound. There is an oxidation reduction reaction which leads to the formation of metallic gold and sulfinic acid derivative of thioglucose.[3]
2 AuSTg → 2Au + TgSSTg
TgSSTg + H2O → TgSOH + TgSH
2TgSOH → TgSO2H + 3TgSH
Overall: 2H2O + 4 AuSTg → 4Au + TgSO2H + 3TgSH
(AuSTg = Gold thioglucose, TgSSTg = Thioglucose disulfide, TgSO2H = sulfinic acid derivative of thioglucose)
[edit] Preparation
Gold thioglucose can be prepared from gold bromide.[4] Gold bromide solution is added into thioglucose solution saturated with sulfur dioxide. Then, ten fold volume of methanol is added and the gold thioglucose is precipitated. The product is recrystallized with water and methanol.
Aurothioglucose has an interaction with the antimalarial medication Hydroxychloroquine.
[edit] See also
[edit] Footnotes
- ^ 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.
- ^ C. F. Shaw III, "Chem. Rev.", 99, 2589 (1999)
- ^ C. F. Shaw III et al., "Journal of Inorganic Biochemistry", 14, 267(1981)
- ^ K. Kataoka et al., "Brain Research Bulletin", 3, 257(1978)
[edit] External links
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