Auranofin

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Structural formula
Structure of Auranofin
General
Non-proprietary name Auranofin
other names

(2,3,4,6- Tetra- O -acetyl-1-thio-β- D -glucopyranosato) (triethylphosphine) gold ( IUPAC )

Molecular formula C 20 H 34 AuO 9 PS
External identifiers / databases
CAS number 34031-32-8
EC number 251-801-9
ECHA InfoCard 100,047,077
PubChem 16667669
DrugBank DB00995
Wikidata Q421230
Drug information
ATC code

M01 CB03

Drug class

Gold preparation

properties
Molar mass 679.49 g mol −1
Physical state

firmly

Melting point

110-111 ° C

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
08 - Dangerous to health

Caution

H and P phrases H: 361
P: 280
Toxicological data

265 mg kg −1 ( LD 50ratoral )

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

Auranofin (trade name: Ridaura ) is an organic gold compound that is used as a medicinal substance in the basic therapy of chronic, progressive polyarthritis . Today it is only used in exceptional cases when other basic therapeutic  agents such as methotrexate fail  .

The mechanism of action of the substance is not known, but it is suspected that auranofin is attached to cysteine ​​residues in the catalytic center of proinflammatory transcription factors e.g. B. of AP-1 and NF-κ-B binds and thus prevents their binding to their DNA consensus sequences . This reduces the expression of inflammatory mediators. There is also discussion about whether the gold will react with the SH groups.

Auranofin can be used orally (in tablet form) and was first approved in 1982. The finished medicinal product is available in many EU countries.

Individual evidence

  1. a b Entry on Auranofin. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.
  2. a b Auranofin data sheet from Sigma-Aldrich , accessed on July 15, 2018 ( PDF ).Template: Sigma-Aldrich / name not given
  3. WHO Drug Information (PDF; 5.7 MB), Vol. 2, No. 1 (1988), p. 7.