Sodium aurothiomalate

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Structural formula
Structural formula of sodium aurothiomalate
General
Surname Sodium aurothiomalate
other names
  • IUPAC : Gold (I) -2-sulfidobutanedioate
  • Gold sodium thiomalate
CAS number 12244-57-4
Monomer Gold (I) thiomalate
Molecular formula of the repeating unit C 4 H 4 AuNaO 4 S
Molar mass of the repeating unit 344.10 g mol −1
PubChem 4479093
ATC code

M01 CB02

Drug information
Drug class

Gold preparation

properties
Physical state

firmly

solubility

very soluble in water

  • practically insoluble in ethanol, ether
safety instructions
Please note the restricted labeling requirements for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 317
P: 280
Toxicological data

440 mg kg −1 ( LD 50 ,  rat ,  iv )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sodium aurothiomalate (also known as gold sodium thiomalate ) is an organometallic compound used to treat rheumatoid arthritis .

Due to the high price and the sometimes considerable side effects - around 50% of the (intramuscular) treatments are discontinued due to the side effects - it is increasingly being displaced by other drugs.

Possible side effects include allergic reactions , nausea , diarrhea , itching, and rashes .

Extraction and presentation

The compound is synthesized by reacting gold (I) iodide with mercaptosuccinic acid in the presence of sodium hydroxide solution .

properties

Sodium aurothiomalate is a light yellow, crystalline compound. In the solid phase, as a result of single-crystal investigations, a polymeric structure consisting of coordinated Au-S units could be detected, which is arranged in a complex double helix structure with a pitch of four Au-S units. A tetragonal crystal lattice is formed. The calculated density is 3.402 g · cm −3 . In aqueous solution, the structure breaks down into oligomeric substructures with 6 to 14 Au-S units.

Trade names

Sodium aurothiomalate is commercially available in Germany and Switzerland under the name Tauredon .

See also

Individual evidence

  1. ↑ a b Data sheet Sodium aurothiomalate (I), 99.9% (metals basis) from AlfaAesar, accessed on December 8, 2019 ( PDF )(JavaScript required) .
  2. ↑ a b c data sheet Sodium aurothiomalate hydrate from Sigma-Aldrich , accessed on April 12, 2011 ( PDF ).
  3. ↑ gold sodium thiomalate . Drugs.com
  4. ^ A. Kleemann, J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications. 4th edition. Thieme 2001, ISBN 3-13-115134-X .
  5. ↑ Patent US 1 994 213 (Rhone-Poulenc 1935).
  6. ↑ WF Kean, CJL Lock, D. Singal, YB Kassam, H. Howard-Lock, J. Rischke: Biological action of colorless and yellow solutions of gold sodium thiomalate on thrombin activity and the mixed lymphocyte reaction. In: J Pharm Sci . 77 (1988), pp. 1033-1036, doi: 10.1002 / jps.2600771209 .
  7. ↑ a b R. Bau: Crystal Structure of the Antiarthritic Drug Gold Thiomalate (Myochrysine): A Double-Helical Geometry in the Solid State. In: J. Am. Chem. Soc. 120 (1998), pp. 9380-9381, doi: 10.1021 / ja9819763 .
  8. ↑ CF Shaw III, NA Schaeffer, RC Elder, MK Eidsness, JM Trooster, GHM Calis: Bovine serum albumin-gold thiomalate complex: gold-197 Moessbauer, EXAFS and XANES, electrophoresis, sulfur-35 radiotracer, and fluorescent probe competition studies. In: J. Am. Chem. Soc. 106 (1984), pp. 3511-3521, doi: 10.1021 / ja00324a019 .