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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| 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  |
| ATC code | M01CB04 |
| PubChem | CID 6104 |
| ChemSpider | 16738764 |
| UNII | 2P2V9Q0E78 |
| ChEMBL | CHEMBL1697725  |
| Synonyms | Gold thioglucose, Solganal, Auromyose |
| Chemical data | |
| Formula | C6H11AuO5S |
| Mol. mass | 392.181 g/mol |
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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.
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History [edit]
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 [edit]
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 [edit]
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 [edit]
In recent research, it was found that injection of gold thioglucose in the mouse induces obesity.[2] Aurothioglucose has an interaction with the antimalarial medication hydroxychloroquine.
See also [edit]
References [edit]
- ^ a b Shaw, III, C. F. (1999). "Gold-Based Therapeutic Agents". Chemical Reviews 99 (9): 2589–600. doi:10.1021/cr980431o. PMID 11749494.
- ^ 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 [edit]
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Wikimedia Commons has media related to: Aurothioglucose |
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