Aurothioglucose Chemical Properties

Melting point:

>107oC (dec.)

storage temp. 

2-8°C

solubility 

H2O: soluble5mg/mL, clear

form 

powder

color 

white to beige

Merck 

13,887

Stability:

Hygroscopic, Light Sensitive

IARC

3 (Vol. 13, Sup 7) 1987

EPA Substance Registry System

Aurothioglucose (12192-57-3)

Safety Information

Hazard Codes 

Xn

Risk Statements 

42/43

Safety Statements 

22-36/37-45

RIDADR 

2811

WGK Germany 

3

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

2843300000

Hazardous Substances Data

12192-57-3(Hazardous Substances Data)

Toxicity

LD50 intravenous in chicken: 1gm/kg

MSDS

• Language:English Provider:(1-D-Glucosylthio)gold

Aurothioglucose Usage And Synthesis

Description

Aurothioglucose is highly water soluble, and its aqueous solutions decompose on long standing. It therefore is available as a suspension in sesame oil. Gold content is approximately 50%. Following IM injection, it is highly protein bound (95%), and peak plasma levels are achieved within 2 to 6 hours. Following a single 50-mg dose, the biological half-life ranges from 3 to 27 days, but following successive weekly doses, the half-life increases to 14 to 40 days after the third dose. The therapeutic effect does not correlate with serum plasma gold levels but appears to depend on total accumulated gold. Aurothioglucose is indicated for the adjunctive treatment of adult and juvenile rheumatoid arthritis.

Chemical Properties

yellow crystals,

History

In 1927, aurothioglucose was found to relieve joint pain when used to treat bacterial endocarditis. The area of chrysotherapy had begun. Subsequent investigations led to an extensive study of gold compounds in Great Britain by the Empire Rheumatism Council, which reported in 1961 that sodium aurothiomalate was effective in slowing the development of progressive joint diseases. Both aurothioglucose and sodium aurothiomalate are orally ineffective and are administered by IM injection. In 1985, the first orally effective gold compound for arthritis, auranofin, was introduced in the United States. Several other gold compounds have been evaluated clinically but do not appear to offer advantages in terms of efficacy or toxicity.

Uses

Aurothioglucose hydrate has been used in redox stress survival assay in human cell lines and for inducing obese phenotype in mice.

Uses

To produce obesity in experimental animals.

brand name

Solganal (Schering, USA, Yugoslavia), Aureotan (BYK Gulden, Germany).

Biochem/physiol Actions

Aurothioglucose, a gold compound used clinically to treat rheumatoid arthritis, has recently been found to be a potent PKCiota-Par6 interaction inhibitor, with an IC50 approximately 1 μM. Disruption of this interaction disrupts a rac1 signaling pathway that is required for transformed growth in non-small-cell lung cancer.

Clinical Use

Aurothioglucose is highly water soluble, and its aqueous solutions decompose on long standing. It therefore is available as a suspension in sesame oil. Gold content is approximately 50%. Following IM injection, it is highly protein bound (95%), and peak plasma levels are achieved within 2 to 6 hours. Following a single 50-mg dose, the biological half-life ranges from 3 to 27 days, but following successive weekly doses, the half-life increases to 14 to 40 days after the third dose. The therapeutic effect does not correlate with serum plasma gold levels but appears to depend on total accumulated gold. Aurothioglucose is indicated for the adjunctive treatment of adult and juvenile rheumatoid arthritis.

Safety Profile

Confirmed carcinogen with experimental carcinogenic and neoplastigenic data. A deadly human poison by an unspecified route. An experimental poison by intramuscular route. Moderately toxic by subcutaneous and intravenous routes. Human systemic effects: nausea or vomiting, cholestatic jaundlce, and eye effects. An experimental teratogen. Other experimental reproductive effects. See also GOLD COMPOUNDS. When heated to decomposition it emits very toxic fumes of SOx. Used to treat rheumatoid arthritis.

Synthesis

Synthesis: gold thioglucose is prepared by adding a solution of gold bromide to an aqueous solution of thioglucose that contains sulfur dioxide. After heating, the product is precipitated by the addition of ethanol.

Purification Methods

Purify it by dissolving it in H2O (0.05g in 1mL) and precipitating it by adding EtOH. It yields yellow crystals with a slight mercaptan odour. It decomposes slowly in H2O, and is soluble in propylene glycol but insoluble in EtOH and other common organic solvents. [Caterson & Taylor FEBS Lett 98 351 1979, Cooney et al. Biochem J 259 651 1989.]

Dosage

Aurothioglucose is an antirheumatic used to treat active progressing rheumatoid arthritis and nondisseminated lupus erythematosus. The drug is administered at weekly intervals by intramuscular injection (10 mg, 25 mg, then 50 mg) until 800 mg to 1 g has been given. If improvement takes place, the drug is then administered at levels that balance the urinary excretion of gold. During this maintenance therapy the interval between injections is lengthened to 3 – 4 weeks.

Aurothioglucose(12192-57-3)Related Product Information

• glucuronic acid
• Sodium thiosulfate
• Thioacetic acid
• GLUCOSAMINE SULFATE
• Sodium thiosulfate pentahydrate
• 2-Thiobarbituric acid
• Thioacetamide
• CALCIUM GLUCOHEPTONATE
• Diethylstilbestrol
• Ammonium thiosulfate
• α-Lipoic Acid
• Glucose oxidase
• Zinc gluconate
• GOLD
• Auranofin
• 6-Mercaptohexan-1-ol
• Hydrogen tetrachloroaurate(III) trihydrate
• Aurothioglucose