WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H330139
CAS#: 12244-57-4 (sodium)
Description: Sodium aurothiomalate (also known as gold sodium thiomalate, gold thiomalate, and gold salt) is a gold compound that is used for its immunosuppressive anti-rheumatic effects. Along with an orally-administered gold salt, auranofin, it is one of only two gold compounds currently employed in modern medicine. Sodium aurothiomalate is used to treat rheumatoid arthritis and other autoimmune diseases. Sodium aurothiomalate has been shown to be effective in reducing inflammation in the treatment of rheumatoid arthritis and other autoimmune diseases, with fewer side effects than nonsteroidal anti-inflammatory drugs (NSAIDs).
Hodoodo Cat#: H330139
Name: Sodium aurothiomalate
CAS#: 12244-57-4 (sodium)
Chemical Formula: C4H3AuNa2O4S
Exact Mass: 0.00
Molecular Weight: 390.070
Elemental Analysis: C, 12.32; H, 0.78; Au, 50.50; Na, 11.79; O, 16.41; S, 8.22
Related CAS #: 4846-27-9 (free acid) 12244-57-4 (sodium) 39377-38-3 (sodium hydrate)
Synonym: Sodium aurothiomalate; gold sodium thiomalate; Aurothiomalate sodium; Miochrysin; Myochrysine; Myocrisin; Myocrisine;
IUPAC/Chemical Name: sodium (S)-((1,2-dicarboxylatoethyl)thio)gold
InChi Key: VXIHRIQNJCRFQX-SQGDDOFFSA-K
InChi Code: InChI=1S/C4H6O4S.Au.2Na/c5-3(6)1-2(9)4(7)8;;;/h2,9H,1H2,(H,5,6)(H,7,8);;;/q;3*+1/p-3/t2-;;;/m0.../s1
SMILES Code: C([C@@H](C(=O)[O-])S[Au])C(=O)[O-].[Na+].[Na+]
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
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The following data is based on the product molecular weight 390.07 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Nummenmaa E, Hämäläinen M, Moilanen LJ, Moilanen T, Vuolteenaho K, Moilanen E. TRPA1 expression is downregulated by dexamethasone and aurothiomalate in human chondrocytes: TRPA1 as a novel factor and drug target in arthritis. RMD Open. 2017 Sep 4;3(2):e000556. doi: 10.1136/rmdopen-2017-000556. eCollection 2017. PubMed PMID: 28912961; PubMed Central PMCID: PMC5588971.
2: Darabi F, Marzo T, Massai L, Scaletti F, Michelucci E, Messori L. Reactions of model proteins with aurothiomalate, a clinically established gold(I) drug: The comparison with auranofin. J Inorg Biochem. 2015 Aug;149:102-7. doi: 10.1016/j.jinorgbio.2015.03.013. Epub 2015 Apr 1. PubMed PMID: 25865000.
3: Tuure L, Hämäläinen M, Moilanen T, Moilanen E. Aurothiomalate inhibits the expression of mPGES-1 in primary human chondrocytes. Scand J Rheumatol. 2015;44(1):74-9. doi: 10.3109/03009742.2014.927917. Epub 2014 Oct 14. PubMed PMID: 25314295.
4: Scharf VF, Farese JP, Siemann DW, Abbott JR, Kiupel M, Salute ME, Milner RJ. Effects of aurothiomalate treatment on canine osteosarcoma in a murine xenograft model. Anticancer Drugs. 2014 Mar;25(3):332-9. doi: 10.1097/CAD.0000000000000061. PubMed PMID: 24304691.
5: Mansfield AS, Fields AP, Jatoi A, Qi Y, Adjei AA, Erlichman C, Molina JR. Phase I dose escalation study of the PKCι inhibitor aurothiomalate for advanced non-small-cell lung cancer, ovarian cancer, and pancreatic cancer. Anticancer Drugs. 2013 Nov;24(10):1079-83. doi: 10.1097/CAD.0000000000000009. PubMed PMID: 23962904; PubMed Central PMCID: PMC3937851.
6: Whitehouse M, Butters D, Vernon-Roberts B. Conditional pharmacology/toxicology V: ambivalent effects of thiocyanate upon the development and the inhibition of experimental arthritis in rats by aurothiomalate (Myocrysin®) and metallic silver. Inflammopharmacology. 2013 Aug;21(4):291-300. doi: 10.1007/s10787-013-0173-9. Epub 2013 May 19. Review. PubMed PMID: 23686086.
7: Ligacheva AA, Ivanova AN, Belsky YP, Belska NV, Trofimova ES, Danilets MG, Dygai AM. Effect of NF-κB inhibitor aurothiomalate on local inflammation in experimental Th1- and Th2-type immune response. Bull Exp Biol Med. 2012 Aug;153(4):472-4. English, Russian. PubMed PMID: 22977847.
8: Janković SM, Djeković A, Bugarčić Z, Janković SV, Lukić G, Folić M, Canović D. Effects of aurothiomalate and gold(III) complexes on spontaneous motility of isolated human oviduct. Biometals. 2012 Oct;25(5):919-25. doi: 10.1007/s10534-012-9558-2. Epub 2012 May 19. PubMed PMID: 22610585.
9: Belsky YP, Ivanova AN, Danilets MG, Belska NV, Ligatcheva AA, Uchasova EG, Reikhart DV. Study of anti-inflammatory action of aurothiomalate, an inhibitor of NF-κB. Bull Exp Biol Med. 2011 Jun;151(2):190-3. PubMed PMID: 22238747.
10: Valachová K, Vargová A, Rapta P, Hrabárová E, Dráfi F, Bauerová K, Juránek I, Soltés L. Aurothiomalate as preventive and chain-breaking antioxidant in radical degradation of high-molar-mass hyaluronan. Chem Biodivers. 2011 Jul;8(7):1274-83. doi: 10.1002/cbdv.201000351. PubMed PMID: 21766448.
11: Alesutan I, Bobbala D, Qadri SM, Estremera A, Föller M, Lang F. Beneficial effect of aurothiomalate on murine malaria. Malar J. 2010 May 7;9:118. doi: 10.1186/1475-2875-9-118. PubMed PMID: 20459650; PubMed Central PMCID: PMC2875225.
12: Nieminen R, Korhonen R, Moilanen T, Clark AR, Moilanen E. Aurothiomalate inhibits cyclooxygenase 2, matrix metalloproteinase 3, and interleukin-6 expression in chondrocytes by increasing MAPK phosphatase 1 expression and decreasing p38 phosphorylation: MAPK phosphatase 1 as a novel target for antirheumatic drugs. Arthritis Rheum. 2010 Jun;62(6):1650-9. doi: 10.1002/art.27409. PubMed PMID: 20178133.
13: Iqbal MS, Taqi SG, Arif M, Wasim M, Sher M. In vitro distribution of gold in serum proteins after incubation of sodium aurothiomalate and auranofin with human blood and its pharmacological significance. Biol Trace Elem Res. 2009 Sep;130(3):204-9. doi: 10.1007/s12011-009-8330-0. Epub 2009 Feb 5. PubMed PMID: 19194667.
14: Trani M, Sorrentino A, Busch C, Landström M. Pro-apoptotic effect of aurothiomalate in prostate cancer cells. Cell Cycle. 2009 Jan 15;8(2):306-13. Epub 2009 Jan 10. PubMed PMID: 19164922.
15: Iqbal MS, Saeed M, Taqi SG. Erythrocyte membrane gold levels after treatment with auranofin and sodium aurothiomalate. Biol Trace Elem Res. 2008 Winter;126(1-3):56-64. doi: 10.1007/s12011-008-8184-x. Epub 2008 Jul 24. PubMed PMID: 18649049.
16: Regala RP, Thompson EA, Fields AP. Atypical protein kinase C iota expression and aurothiomalate sensitivity in human lung cancer cells. Cancer Res. 2008 Jul 15;68(14):5888-95. doi: 10.1158/0008-5472.CAN-08-0438. PubMed PMID: 18632643; PubMed Central PMCID: PMC2662432.
17: Nieminen R, Vuolteenaho K, Riutta A, Kankaanranta H, van der Kraan PM, Moilanen T, Moilanen E. Aurothiomalate inhibits COX-2 expression in chondrocytes and in human cartilage possibly through its effects on COX-2 mRNA stability. Eur J Pharmacol. 2008 Jun 10;587(1-3):309-16. doi: 10.1016/j.ejphar.2008.03.016. Epub 2008 Mar 29. PubMed PMID: 18448096.
18: Wood PL, Khan MA, Moskal JR. Mechanism of action of the disease-modifying anti-arthritic thiol agents D-penicillamine and sodium aurothiomalate: restoration of cellular free thiols and sequestration of reactive aldehydes. Eur J Pharmacol. 2008 Feb 2;580(1-2):48-54. Epub 2007 Oct 30. PubMed PMID: 18022616.
19: Stuhlmeier KM. The anti-rheumatic gold salt aurothiomalate suppresses interleukin-1beta-induced hyaluronan accumulation by blocking HAS1 transcription and by acting as a COX-2 transcriptional repressor. J Biol Chem. 2007 Jan 26;282(4):2250-8. Epub 2006 Nov 3. PubMed PMID: 17085450.
20: Erdogan E, Lamark T, Stallings-Mann M, Lee Jamieson, Pellecchia M, Thompson EA, Johansen T, Fields AP. Aurothiomalate inhibits transformed growth by targeting the PB1 domain of protein kinase Ciota. J Biol Chem. 2006 Sep 22;281(38):28450-9. Epub 2006 Jul 22. Erratum in: J Biol Chem. 2007 Mar 30;282(13):10132. Pellechia, Mauricio [corrected to Pellecchia, Maurizio]. PubMed PMID: 16861740.
