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Substance Name: Auranofin [USAN:INN:BAN:JAN]
RN: 34031-32-8
UNII: 3H04W2810V
InChIKey: AUJRCFUBUPVWSZ-XTZHGVARSA-M

Note

  • An oral chrysotherapeutic agent for the treatment of rheumatoid arthritis. Its exact mechanism of action is unknown, but it is believed to act via immunological mechanisms and alteration of lysosomal enzyme activity. Its efficacy is slightly less than that of injected gold salts, but it is better tolerated, and side effects which occur are potentially less serious.

Molecular Formula

  • C20-H34-Au-O9-P-S

Molecular Weight

  • 678.49
 

Classification Codes

  • Antirheumatic
  • Antirheumatic Agents
  • Human Data
  • Mutation Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Auranofin
  • Auranofin [USAN:INN:BAN:JAN]

MeSH Heading

  • Auranofin

Synonyms

  • (1-Thio-beta-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetate
  • 2,3,4,6-Tetra-O-acetyl-1-thio-beta-D-glucopyranosato-S (triethylphosphine)gold
  • Auranofin
  • Auranofina
  • Auranofina [INN-Spanish]
  • Auranofine
  • Auranofine [INN-French]
  • Auranofinum
  • Auranofinum [INN-Latin]
  • EINECS 251-801-9
  • HSDB 7172
  • Ridaura
  • SK&F 39162
  • SK&F 39162D
  • SK&F D-39162
  • SKF-39162d
  • Triethylphosphine gold
  • UNII-3H04W2810V

Systematic Names

  • Auranofin
  • Gold, (1-thio-beta-D-glucopyranosato-S)(triethylphosphine)-, 2,3,4,6-tetraacetate
  • Gold, (1-thio-beta-D-glucopyranose 2,3,4,6-tetraacetato-S)(triethylphosphine)- (9CI)
  • Gold, (2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranosato-S)(triethylphosphine)-

Superlist Name

  • Auranofin

Registry Numbers

CAS Registry Number

  • 34031-32-8

FDA UNII

  • 3H04W2810V

System Generated Number

  • 0034031328

Structure Descriptors

InChI

1S/C14H20O9S.C6H15P.Au/c1-6(15)19-5-10-11(20-7(2)16)12(21-8(3)17)13(14(24)23-10)22-9(4)18;1-4-7(5-2)6-3;/h10-14,24H,5H2,1-4H3;4-6H2,1-3H3;/q;;+1/p-1/t10-,11-,12+,13-,14+;;/m1../s1

InChIKey

AUJRCFUBUPVWSZ-XTZHGVARSA-M

Smiles

O1[C@@H](S\[Au]=P(\CC)(CC)CC)[C@@H]([C@H]([C@@H](OC(C)=O)[C@H]1COC(=O)C)OC(=O)C)OC(C)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 3200ug/kg (3.2mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 1106, 1986.
man TDLo oral 1200ug/kg/2W- (1.2mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH Journal of Rheumatology. Vol. 13, Pg. 228, 1986.
mouse LD50 intraperitoneal 33800ug/kg (33.8mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 1106, 1986.
mouse LD50 intravenous 22600ug/kg (22.6mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 1106, 1986.
mouse LD50 oral 84940ug/kg (84.94mg/kg)   Bollettino Chimico Farmaceutico. Vol. 128, Pg. 22, 1989.
mouse LD50 subcutaneous 53600ug/kg (53.6mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 1106, 1986.
rat LD50 intraperitoneal 25500ug/kg (25.5mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 1106, 1986.
rat LD50 intravenous 39mg/kg (39mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 1106, 1986.
rat LD50 oral 265mg/kg (265mg/kg)   Veterinary Pathology. Vol. 15(Suppl,
rat LD50 subcutaneous 235mg/kg (235mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 1106, 1986.
women TDLo oral 5400ug/kg/10D (5.4mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: TOXIC PSYCHOSIS

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Arthritis and Rheumatism. Vol. 27, Pg. 1316, 1984.