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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H11O5S.Au
Molecular Weight 392.18
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AUROTHIOGLUCOSE

SMILES

[Au+].OC[C@H]1O[C@H]([S-])[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=XHVAWZZCDCWGBK-WYRLRVFGSA-M
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

HIDE SMILES / InChI

Molecular Formula Au
Molecular Weight 196.9666
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C6H11O5S
Molecular Weight 195.214
Charge -1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Aurothioglucose (trade name Solganal), also known as gold thioglucose, is a glucose derivative formerly used to treat rheumatoid arthritis, that cannot be adequately controlled by other medicines. Aurothioglucose has been shown to inhibit protein kinase C, a metalloenzyme containing Zn(2+) bound to cysteine and histidine residues, which plays a crucial role in intracellular signal transduction by phosphorylating serine/threonine residues in the protein. The inhibition of protein kinase C has been suggested as a possible mode of action for the therapeutic antirheumatic action of gold drugs. In 2001, aurothioglucose was withdrawn from the Dutch market, where it had been the only injectable gold preparation available since 1943, forcing hospitals to change medication for a large number of patients to aurothiomalate. The drug had been in use for more than 70 years, and four years later the reasons for its sudden disappearance remained unclear.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
65.0 nM [IC50]
80.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Solganal

Doses

AEs

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
10 mg IM one time as a test dose. Observe for 15-30 minutes for adverse/allergic reaction. 25 mg IM one week later and repeat in another week. 50 mg IM once a week until a cumulative dose of 0.8 to 1 G has been reached. If a clinical response has been documented, the dosage may be reduced to a maintenance dosage of 50 mg intramuscularly every three to four weeks. This maintenance dosage may be continued indefinitely based on this patient's response to and tolerance of aurothioglucose.
Route of Administration: Intramuscular
In Vitro Use Guide
The human monocytic cell line latently infected with HIV-1, OM10.1, and the human T cell line latently infected with HIV-1, Ach2, were maintained at 0.2–1.0^3-10^6 cells/ml in RPMI 1640 supplemented with 10% (v/v) FCS. To maintain the latency of the HIV-1 in these cells, 20 M AZT (Zidovudine) was added in culture media and was excluded at least 2 weeks before experiments. Cultures were incubated with AuTG (Aurothioglucose) for either 3, 6 or 12 days and the cell media were changed every 3 days.
Substance Class Chemical
Record UNII
2P2V9Q0E78
Record Status Validated (UNII)
Record Version