Sodium aurothiomalate

Last updated

Sodium aurothiomalate
Sodium aurothiomalate.svg
Clinical data
Trade names Myocrisin
AHFS/Drugs.com Multum Consumer Information
License data
Pregnancy
category
  • AU:B2
Routes of
administration
Intramuscular
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US:Discontinued
Pharmacokinetic data
Protein binding High [1]
Elimination half-life 6-25 days [1]
Excretion Urine (60–90%), faeces (10–40%) [1]
Identifiers
  • Sodium 2-(auriosulfanyl)-3-carboxypropanoate
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard 100.032.242 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C4H4AuNaO4S
Molar mass 368.09 g·mol−1
3D model (JSmol)
  • [Au+].[Na+].[O-]C(=O)C([S-])CC(=O)O
  • 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 Yes check.svgY
  • Key:LTEMOXGFFHXNNS-UHFFFAOYSA-L Yes check.svgY
   (verify)

Sodium aurothiomalate (INN, known in the United States as gold sodium thiomalate) is a gold compound that is used for its immunosuppressive anti-rheumatic effects. [2] [3] Along with an orally-administered gold salt, auranofin, it is one of only two gold compounds currently employed in modern medicine. [4]

Contents

Medical uses

It is primarily given once or twice weekly by intramuscular injection for moderate-severe rheumatoid arthritis. It was also once used to treat tuberculosis, though later trials showed it to be harmful and ineffective for that purpose. [5]

Adverse effects

Its most common side effects are digestive (mostly dyspepsia, mouth swelling, nausea, vomiting and taste disturbance), vasomotor (mostly flushing, fainting, dizziness, sweating, weakness, palpitations, shortness of breath and blurred vision) or dermatologic (usually itchiness, rash, local irritation near to the injection site and hair loss) in nature, although conjunctivitis, blood dyscrasias, kidney damage, joint pain, muscle aches/pains and liver dysfunction are also common. [6] Less commonly, it can cause gastrointestinal bleeding, dry mucous membranes and gingivitis. [6] Rarely it can cause aplastic anaemia, ulcerative enterocolitis, difficulty swallowing, angiooedema, pneumonitis, pulmonary fibrosis, hepatotoxicity, cholestatic jaundice, peripheral neuropathy, Guillain–Barré syndrome, encephalopathy, encephalitis and photosensitivity. [6]

Pharmacology

Its precise mechanism of action is unknown but sodium aurothiomalate is known to inhibit the synthesis of prostaglandins. [4] It also modulates phagocytic cells and inhibits class II major histocompatibility complex-peptide interactions. [4] It is also known that it inhibits the following enzymes: [4] [7]

History of use

Reports of favorable use of the compound were published in France in 1929 by Jacques Forestier. [9] 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 Raoul Dufy'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." [10]

Along with aurothioglucose, sodium aurothiomalate was discontinued worldwide in 2019 by its manufacturer Sanofi [11] due to a worldwide gold shortage, [12] leaving generic forms of Auranofin the only gold-based drug available in the United States. [13] [14]

References

  1. 1 2 3 "aurothiomalate, sodium, Myochrysine (gold sodium thiomalate) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Retrieved 13 March 2014.
  2. Jessop JD, O'Sullivan MM, Lewis PA, Williams LA, Camilleri JP, Plant MJ, et al. (September 1998). "A long-term five-year randomized controlled trial of hydroxychloroquine, sodium aurothiomalate, auranofin and penicillamine in the treatment of patients with rheumatoid arthritis". British Journal of Rheumatology. 37 (9): 992–1002. doi: 10.1093/rheumatology/37.9.992 . PMID   9783766.
  3. Iqbal MS, Saeed M, Taqi SG (2008). "Erythrocyte membrane gold levels after treatment with auranofin and sodium aurothiomalate". Biological Trace Element Research. 126 (1–3): 56–64. Bibcode:2008BTER..126...56I. doi:10.1007/s12011-008-8184-x. PMID   18649049. S2CID   20169992.
  4. 1 2 3 4 Kean WF, Kean IR (June 2008). "Clinical pharmacology of gold". Inflammopharmacology. 16 (3): 112–125. doi:10.1007/s10787-007-0021-x. PMID   18523733. S2CID   808858.
  5. Benedek TG (January 2004). "The history of gold therapy for tuberculosis". Journal of the History of Medicine and Allied Sciences. 59 (1): 50–89. doi:10.1093/jhmas/jrg042. PMID   15011812. S2CID   37436710.
  6. 1 2 3 Rossi S, ed. (2013). Australian Medicines Handbook (2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust. ISBN   978-0-9805790-9-3.
  7. Berners-Price SJ, Filipovska A (September 2011). "Gold compounds as therapeutic agents for human diseases". Metallomics. 3 (9): 863–873. doi: 10.1039/c1mt00062d . PMID   21755088.
  8. Tuure L, Hämäläinen M, Moilanen T, Moilanen E (2014). "Aurothiomalate inhibits the expression of mPGES-1 in primary human chondrocytes". Scandinavian Journal of Rheumatology. 44 (1): 74–79. doi:10.3109/03009742.2014.927917. PMID   25314295. S2CID   5213201.
  9. Freyberg RH, Block WD, Levey S (July 1941). "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". The Journal of Clinical Investigation. 20 (4): 401–412. doi:10.1172/jci101235. PMC   435072 . PMID   16694848.
  10. Lamboley C (December 6, 2010). "Deux rhumatisants au soleil du Midi : Renoir et Dufy" [Two rheumatic in the Midi sun: Renoir and Dufy](PDF). Académie des Sciences et Lettres de Montpellier (in French). Montpellier. Retrieved July 7, 2015.
  11. "Myocrisin (Sodium aurothiomalate) injection: Permanent discontinuation end of supply in 2019" (PDF). Sanofi. Aventis Pharma Ltd. 10 June 2019. Retrieved 28 August 2025.
  12. "Myocrisin permanent discontinuation". Letters and drug alerts sent to healthcare professionals in June 2019. © Crown of the United Kingdom. 17 July 2019. Retrieved 28 August 2025.
  13. Stanway JA, Walker D (4 January 2022). "Inflammatory arthritis-the end of the golden age". Rheumatology Advances in Practice. 6 (1) rkac015. British Society for Rheumatology. doi:10.1093/rap/rkac015. PMC   8902173 . PMID   35265790.
  14. "June 2025 Pharmacy & Therapeutics Committee Decisions" (PDF). Aspirus Health. June 2025. Retrieved 28 August 2025.