12192-57-3, Gold thioglucose, CAS:12192-57-3

12192-57-3, Gold thioglucose,
CAS:12192-57-3
C6H11AuO5S / 392.18

葡糖硫金, Gold thioglucose

Aurothioglucose is a drug that belongs to the class of glucocorticoids. It is used as an adjunct in the treatment of rheumatoid arthritis, inflammatory bowel disease, and injury. Aurothioglucose has been shown to inhibit protein oxidation and DNA binding activity by preventing the formation of reactive oxygen species (ROS). This drug also has the ability to reduce inflammation by inhibiting the release of prostaglandins from cells. Aurothioglucose can be used as a substitute for prednisone when treating conditions such as kidney injury or body protein loss.

Aurothioglucose, also known as gold thioglucose, was formerly used to treat rheumatoid arthritis. Contemporary research on the effect of gold salts treatment began in 1935, primarily to reduce inflammation and to slow disease progression in patients with rheumatoid arthritis. The use of gold compounds has decreased since the 1980s owing to numerous side effects, limited efficacy, and slow onset of action. Many if not most gold compounds that were indicated for rheumatoid arthritis therapy have since been replaced with the use of various current disease modifying anti-rheumatic drugs (DMARDs) like methotrexate and others, which are far more effective.

Aurothioglucose is a member of oxanes.

A thioglucose derivative used as an antirheumatic and experimentally to produce obesity in animals.

Title: Aurothioglucose

CAS Registry Number: 12192-57-3

CAS Name: (1-Thio-D-glucopyranosato-O2,S1)gold

Additional Names: (1-D-glucosylthio)gold; gold thioglucose

Trademarks: Aureotan (Byk Gulden); Solganal (Schering)

Molecular Formula: C6H11AuO5S

Molecular Weight: 392.18

Percent Composition: C 18.38%, H 2.83%, Au 50.22%, O 20.40%, S 8.18%

Literature References: Disease modifying antirheumatic drug (DMARD). Prepn: Lebeau-Janot, Traité Pharm. Chim. II, 661 (1956). Induction of obesity in exptl animals: A. F. Debons et al., Fed. Proc. 36, 143 (1977). Clinical comparison with auranofin, q.v., in rheumatoid arthritis: P. L. C. M. Van Riel et al., Clin. Rheumatol. 5, 359 (1986); P. E. Prete et al., Clin. Rheumatol. 13, 60 (1994).

Properties: Yellow crystals. Slight mercaptan-like odor. Sol in water with decompn; slightly sol in propylene glycol. Practically insol in acetone, alcohol, chloroform, ether.

Use: To produce obesity in exptl animals.

Therap-Cat: Antirheumatic.

Keywords: Antiarthritic/Antirheumatic.

CAS Number	12192-57-3
Product Name	Aurothioglucose
IUPAC Name	gold(1+);(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-thiolate
Molecular Formula	C6H11AuO5S · xH2O
Molecular Weight	392.18 g/mol
InChI	InChI=1S/C6H12O5S.Au/c7-1-2-3(8)4(9)5(10)6(12)11-2;/h2-10,12H,1H2;/q;+1/p-1/t2-,3-,4+,5-,6?;/m1./s1
InChI Key	DWHOHDLMDHWAKJ-ZXFLYBOBSA-M
SMILES	C(C1C(C(C(C(O1)[S-])O)O)O)O.[Au+]
Solubility	Slightly soluble in propylene glycol; practically insoluble in acetone, alcohol, chloroform, and ether Soluble in water with decomposition.
Synonyms	Aureotan, Auromyose, Aurothioglucose, Aurothioglucose, beta D Isomer, Aurothioglucose, beta-D Isomer, Aurothioglucose, Sodium Salt, beta-D Isomer, B Oleosum, Solganal, beta-D Isomer Aurothioglucose, Gold 50, Gold Thioglucose, Gold-50, Gold50, Oleosum, Solganal B, Solganal, Solganal B Oleosum, Solganol, Thioglucose, Gold, Thioglucosoaurate
Canonical SMILES	C(C1C(C(C(C(O1)[S-])O)O)O)O.[Au+]
Isomeric SMILES	C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)[S-])O)O)O)O.[Au+]

COA:

Name: Aurothioglucose; (1-Thio-d-glucopyranosato)gold

CAS: 12192-57-3 M.F.: C6H11AuO5S M.W._:392.18

*Items*	*Standards*	*Results*
Appearance	A yellowish solid	Positive
Solubility	Soluble in water, insoluble in most organic solvent	Complies
Identification	TLC	Complies
Elemental Sulfur	Should comply	Complies
Loss Weight On Dryness	Max. 1%	0.74%
Optical Activity (10 mg per mL, in water)	α]23/D = +65° ~ +75°,	+68.3°
Assay	95% ~ 105%	98.2%