Revision as of 09:27, 23 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 461994331 of page Sodium_aurothiomalate for the Chem/Drugbox validation project (updated: 'UNII', 'CASNo'). |
Latest revision as of 09:43, 7 January 2025 edit 2601:2c4:483:53a0:55e3:9c5d:518:4373 (talk) Corrected erroneous claim that it has "proven to be effective in treating tuberculosis" (cited study claims the opposite) |
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{{Short description|Pharmaceutical drug}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Infobox drug |
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{{chembox |
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| IUPAC_name = Sodium 2-(auriosulfanyl)-3-carboxypropanoate |
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| Verifiedfields = changed |
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| image=Sodium aurothiomalate.svg |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| width=200px |
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| UNII = <!-- blanked - oldvalue: E4768ZY6GM --> |
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| verifiedrevid = 395218589 |
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| verifiedrevid = 462079279 |
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<!--Clinical data--> |
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| ImageFile=Sodium aurothiomalate.svg |
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| tradename = Myocrisin |
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| ImageSize=200px |
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| Drugs.com = {{drugs.com|mtm|gold-sodium-thiomalate}} |
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| PIN = Sodium aurothiomalate |
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| licence_US = Gold_sodium_thiomalate |
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| SystematicName = Sodium 2-(auriosulfanyl)-3-carboxypropanoate |
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| pregnancy_AU = B2 |
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| Section1 = {{Chembox Identifiers |
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| pregnancy_US = C |
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| InChI1 = 1/C4H6O4S.Au.Na/c5-3(6)1-2(9)4(7)8;;/h2,9H,1H2,(H,5,6)(H,7,8);;/q;2*+1/p-2 |
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| legal_AU = S4 |
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| InChIKey1 = LTEMOXGFFHXNNS-NUQVWONBAQ |
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| legal_CA = Rx-only |
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| CASNo = <!-- blanked - oldvalue: 12244-57-4 --> |
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| legal_UK = POM |
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| CASNo_Ref = {{cascite | correct | ??}} |
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| legal_US = Discontinued |
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| PubChem = 16760302 |
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| routes_of_administration = ] |
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| PubChem_Ref = {{Pubchemcite | correct | PubChem}} |
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<!--Pharmacokinetic data--> |
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| ChemSpiderID = 7827788 |
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| protein_bound = High<ref name = MSR>{{cite web|title=aurothiomalate, sodium, Myochrysine (gold sodium thiomalate) dosing, indications, interactions, adverse effects, and more|work=Medscape Reference|publisher=WebMD|access-date=13 March 2014|url=http://reference.medscape.com/drug/aurothiomalate-sodium-myochrysine-gold-sodium-thiomalate-343218#showall}}</ref> |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| elimination_half-life = 6-25 days<ref name = MSR/> |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| excretion = Urine (60-90%), faeces (10-40%)<ref name = MSR/> |
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| CAS_number = 12244-57-4 |
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| PubChem = 16760302 |
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| ChemSpiderID = 7827788 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 35863 |
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| ChEBI = 35863 |
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| ATCCode_prefix = M01 |
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| ATC_prefix = M01 |
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| ATCCode_suffix = CB01 |
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| ATC_suffix = CB01 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C4H6O4S.Au.Na/c5-3(6)1-2(9)4(7)8;;/h2,9H,1H2,(H,5,6)(H,7,8);;/q;2*+1/p-2 |
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| StdInChI = 1S/C4H6O4S.Au.Na/c5-3(6)1-2(9)4(7)8;;/h2,9H,1H2,(H,5,6)(H,7,8);;/q;2*+1/p-2 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = LTEMOXGFFHXNNS-UHFFFAOYSA-L |
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| StdInChIKey = LTEMOXGFFHXNNS-UHFFFAOYSA-L |
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| SMILES = ..C(=O)C()CC(=O)O |
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| smiles = ..C(=O)C()CC(=O)O |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| InChI = 1S/C4H6O4S.Au.Na/c5-3(6)1-2(9)4(7)8;;/h2,9H,1H2,(H,5,6)(H,7,8);;/q;2*+1/p-2 |
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| UNII = E4768ZY6GM |
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| InChIKey = LTEMOXGFFHXNNS-UHFFFAOYSA-L |
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<!--Chemical data--> |
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| Gmelin = 1211734}} |
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| chemical_formula = |
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| Section2 = {{Chembox Properties |
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| C=4 | H=4 | Au=1 | Na=1 | O=4 | S=1 |
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| C = 4 |
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| H = 4 |
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| Au = 1 |
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| Na = 1 |
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| O = 4 |
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| S = 1 |
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| ExactMass = 367.939350590 g mol<sup>-1</sup>}} |
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| Section3 = {{Chembox Pharmacology |
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| Bioavail = 0% |
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| AdminRoutes = Intramascular injection |
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| Legal_UK = POM}} |
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}} |
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}} |
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'''Sodium aurothiomalate''' (], known in the ] as '''gold sodium thiomalate''') is a ] that is used for its immunosuppressive ] effects.<ref>{{cite journal | vauthors = Jessop JD, O'Sullivan MM, Lewis PA, Williams LA, Camilleri JP, Plant MJ, Coles EC | title = A long-term five-year randomized controlled trial of hydroxychloroquine, sodium aurothiomalate, auranofin and penicillamine in the treatment of patients with rheumatoid arthritis | journal = British Journal of Rheumatology | volume = 37 | issue = 9 | pages = 992–1002 | date = September 1998 | pmid = 9783766 | doi = 10.1093/rheumatology/37.9.992 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Iqbal MS, Saeed M, Taqi SG | title = Erythrocyte membrane gold levels after treatment with auranofin and sodium aurothiomalate | journal = Biological Trace Element Research | volume = 126 | issue = 1–3 | pages = 56–64 | year = 2008 | pmid = 18649049 | doi = 10.1007/s12011-008-8184-x | s2cid = 20169992 }}</ref> Along with an orally-administered gold salt, ], it is one of only two gold compounds currently employed in modern medicine.<ref name = mech08>{{cite journal | vauthors = Kean WF, Kean IR | title = Clinical pharmacology of gold | journal = Inflammopharmacology | volume = 16 | issue = 3 | pages = 112–25 | date = June 2008 | pmid = 18523733 | doi = 10.1007/s10787-007-0021-x | s2cid = 808858 }}</ref> |
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==Medical uses== |
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It is primarily given once or twice weekly by intramuscular injection for moderate-severe ]. It was also once used to treat ], though later trials showed it to be harmful and ineffective for that purpose.<ref>{{cite journal | vauthors = Benedek TG | title = The history of gold therapy for tuberculosis | journal = Journal of the History of Medicine and Allied Sciences | volume = 59 | issue = 1 | pages = 50–89 | date = January 2004 | pmid = 15011812 | doi = 10.1093/jhmas/jrg042 | s2cid = 37436710 }}</ref> |
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==Adverse effects== |
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Its most common side effects are digestive (mostly ], ], nausea, vomiting and taste disturbance), vasomotor (mostly flushing, fainting, dizziness, sweating, weakness, palpitations, ] and blurred vision) or dermatologic (usually itchiness, rash, local irritation near to the injection site and hair loss) in nature, although ], blood dyscrasias, kidney damage, ], ] and liver dysfunction are also common.<ref name="AMH">{{cite book | veditors = Rossi S | isbn = 978-0-9805790-9-3 | title = Australian Medicines Handbook | place = Adelaide | publisher = The Australian Medicines Handbook Unit Trust | year = 2013 | edition = 2013 }}</ref> Less commonly, it can cause ], dry mucous membranes and ].<ref name = AMH/> Rarely it can cause ], ulcerative ], ], ], ], ], hepatotoxicity, ], ], ], ], ] and ].<ref name = AMH/> |
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==Pharmacology== |
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Its precise mechanism of action is unknown but is known that it inhibits the synthesis of ].<ref name = mech08/> It also modulates ] and inhibits class II ]-peptide interactions.<ref name = mech08/> It is also known that it inhibits the following enzymes:<ref name = mech08/><ref name = rsc>{{cite journal | vauthors = Berners-Price SJ, Filipovska A | title = Gold compounds as therapeutic agents for human diseases | journal = Metallomics | volume = 3 | issue = 9 | pages = 863–73 | date = September 2011 | pmid = 21755088 | doi = 10.1039/c1mt00062d | doi-access = free }}</ref> |
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* ]<ref>{{cite journal | vauthors = Tuure L, Hämäläinen M, Moilanen T, Moilanen E | title = Aurothiomalate inhibits the expression of mPGES-1 in primary human chondrocytes | journal = Scandinavian Journal of Rheumatology | volume = 44 | issue = 1 | pages = 74–9 | year = 2014 | pmid = 25314295 | doi = 10.3109/03009742.2014.927917 | s2cid = 5213201 | url = http://tampub.uta.fi/handle/10024/99703 }}</ref> |
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==History of use== |
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Reports of favorable use of the compound were published in France in 1929 by ].<ref name=freyberg>{{cite journal | vauthors = Freyberg RH, Block WD, Levey S | title = Metabolism, Toxicity and Manner of Action of Gold Compounds Used in the Treatment of Arthritis. I. Human Plasma and Synovial Fluid Concentration and Urinary Excretion of Gold During and Following Treatment With Gold Sodium Thiomalate, Gold Sodium Thiosulfate, and Colloidal Gold Sulfide | journal = The Journal of Clinical Investigation | volume = 20 | issue = 4 | pages = 401–12 | date = July 1941 | pmid = 16694848 | pmc = 435072 | doi = 10.1172/jci101235 }}</ref> The use of gold salts was then a controversial treatment and was not immediately accepted by the international community. Success was found in the treatment of ]'s joint pain by the use of gold salts in 1940; "(the treatment) brought in a few weeks such a spectacular sense of healing, that Dufy ... boasted of again having the ability to catch a tram on the move."<ref>{{cite journal |last=Lamboley |first=Claude | name-list-style = vanc |date=December 6, 2010 |title=Deux rhumatisants au soleil du Midi : Renoir et Dufy |trans-title=Two rheumatic in the Midi sun: Renoir and Dufy |url=http://www.ac-sciences-lettres-montpellier.fr/academie_edition/fichiers_conf/LAMBOLEY-2010.pdf |language= fr|journal=Académie des Sciences et Lettres de Montpellier |location=Montpellier |access-date=July 7, 2015 }}</ref> |
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Along with ], sodium aurothiomalate was discontinued in the United States, leaving ] as the only gold salt remaining on the U.S. market.{{when?|date=March 2024}}{{cn|date=March 2024}} |
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== References == |
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{{reflist|30em}} |
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{{Antirheumatic products}} |
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{{Gold compounds}} |
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{{DEFAULTSORT:Sodium Aurothiomalate}} |
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