AUROTHIOGLUCOSE

First approved in 1949

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 Search

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	196.966569
Charge	1
Count

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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugs.com/cdi/aurothioglucose.html
Curator's Comment: description was created based on several sources, including https://www.drugbank.ca/drugs/DB09121 | https://www.ncbi.nlm.nih.gov/pubmed/15940762 | https://www.ncbi.nlm.nih.gov/pubmed/6785260 | https://www.ncbi.nlm.nih.gov/pubmed/2510733 | https://www.ncbi.nlm.nih.gov/pubmed/15940754

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 In 2001, aurothioglucose was withdrawn from the Dutch market, where it had been the only injectable gold preparation available since 1943, forcing hospitals to change medication for a large number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 Target	Pharmacology	Potency
Protein kinase C, PKC; classical/novel 4 Target ID: CHEMBL2096620 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2510733	Inhibitor 8504
Thioredoxin reductase 1 2 Target ID: CHEMBL1927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24295151	Inhibitor 8504	65.0 nM [IC50]
Glutathione peroxidase 1 1 Target ID: CHEMBL2163186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9685351	Inhibitor 8504	80.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 320 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2885986	Primary		Approved 8583	Solganal Approved Use Unknown

Doses

Dose	Population	Adverse events
500 mg 1 times / week multiple, intramuscular Studied dose Dose: 500 mg, 1 times / week Route: intramuscular Route: multiple Dose: 500 mg, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/3130212/	unhealthy, 35 to 86 years Health Status: unhealthy Age Group: 35 to 86 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3130212/	Sources: https://pubmed.ncbi.nlm.nih.gov/3130212/
50 mg 1 times / 4 days multiple, intramuscular Recommended Dose: 50 mg, 1 times / 4 days Route: intramuscular Route: multiple Dose: 50 mg, 1 times / 4 days Sources: https://pubmed.ncbi.nlm.nih.gov/6421293/	unhealthy, 43 years Health Status: unhealthy Age Group: 43 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/6421293/	Other AEs: Hepatitis... Other AEs: Hepatitis Sources: https://pubmed.ncbi.nlm.nih.gov/6421293/
50 mg 1 times / week multiple, intramuscular Recommended Dose: 50 mg, 1 times / week Route: intramuscular Route: multiple Dose: 50 mg, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/13703724/	unhealthy, 56 years Health Status: unhealthy Age Group: 56 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/13703724/	Other AEs: Loeffler's syndrome... Other AEs: Loeffler's syndrome Sources: https://pubmed.ncbi.nlm.nih.gov/13703724/
50 mg 1 times / week multiple, intramuscular Recommended Dose: 50 mg, 1 times / week Route: intramuscular Route: multiple Dose: 50 mg, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/1978639/	unhealthy, 56 years Health Status: unhealthy Age Group: 56 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/1978639/	Disc. AE: Thrombocytopenia... AEs leading to discontinuation/dose reduction: Thrombocytopenia (grade 3) Sources: https://pubmed.ncbi.nlm.nih.gov/1978639/
50 mg 1 times / week multiple, intramuscular Recommended Dose: 50 mg, 1 times / week Route: intramuscular Route: multiple Dose: 50 mg, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/6415865/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6415865/	Disc. AE: Dermatitis, Stomatitis... AEs leading to discontinuation/dose reduction: Dermatitis (grade 3, 44%) Stomatitis (grade 3, 4%) Proteinuria (grade 3, 4%) Polyneuropathy (grade 3, 4%) Sources: https://pubmed.ncbi.nlm.nih.gov/6415865/
50 mg 1 times / week multiple, intramuscular Recommended Dose: 50 mg, 1 times / week Route: intramuscular Route: multiple Dose: 50 mg, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/6432414/	unhealthy, mean age 56 years Health Status: unhealthy Age Group: mean age 56 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6432414/	Disc. AE: Dermatitis, Stomatitis... Other AEs: Dermatitis, Loose stools... AEs leading to discontinuation/dose reduction: Dermatitis (30.8%) Stomatitis (3.8%) Proteinuria (3.8%) Polyneuropathy (3.8%) IgA deficiency (3.8%) Other AEs: Dermatitis (57.7%) Loose stools (3.8%) Stomatitis (7.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/6432414/

AEs

Sourcing

Vendor/Aggregator	ID	URL
AK Scientific, Inc. (AKSCI)	3457AH	http://www.aksci.com/item_detail.php?cat=3457AH
Alfa Chemistry	ALP12192573	https://reagents.alfa-chemistry.com/product/aurothioglucose-hydrate-cas-12192-57-3-anhydrous-56.html
Alfa Chemistry	AP12192573	https://reagents.alfa-chemistry.com/product/aurothioglucose-cas-12192-57-3-2905.html
Ambinter	Amb22351187	http://www.ambinter.com/reference/22351187
Avantor Inc	101096-700	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101096-700
BioCrick	BCC5446	http://www.biocrick.com/Aurothioglucose-BCC5446.html
BOC Sciences	12192-57-3	https://www.bocsci.com/aurothioglucose-cas-12192-57-3-item-84-55856.html
eNovation Chemicals	D676617	https://www.enovationchem.com/ProductDetails.asp?ProductID=D676617
Glentham Life Sciences	GK8154	http://www.glentham.com/products/product/GK8154/
iChemical	EBD31793	http://www.ichemical.com/chemicals/cas-12192-57-3
Molcore	MC512396	https://www.molcore.com/product/12192-57-3
OChem	15591	http://www.ocheminc.com/index.php?act=psearch&pid=192A573

PubMed

Title	Date	PubMed
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013-09-05	23769903
A novel and comprehensive mouse model of human non-alcoholic steatohepatitis with the full range of dysmetabolic and histological abnormalities induced by gold thioglucose and a high-fat diet.	2011-04	21382165
Substrate and inhibitor specificities differ between human cytosolic and mitochondrial thioredoxin reductases: Implications for development of specific inhibitors.	2011-03-15	21172426
The inhibitory effect of disease-modifying anti-rheumatic drugs and steroids on gliostatin/platelet-derived endothelial cell growth factor production in human fibroblast-like synoviocytes.	2005-10	15990992
Endogenous reductants support the catalytic function of recombinant rat cyt19, an arsenic methyltransferase.	2004-03	15025511
Thiol-reactive metal compounds inhibit NF-kappa B activation by blocking I kappa B kinase.	2000-06-01	10820281
Sterile oily abscess from depot gold therapy.	1993-11	8240442
Effects of thioglucoses on sensitivity to insulin hypoglycemic convulsions.	1986-05	3084764
Gold thioglucose selectively damages dorsal vagal nuclei.	1986-03-05	3084036
Thioglucose interactions with a "gold thioglucose-lesioned glucostat".	1985-09	3928877
Glycolytic concomitant of brain inflammation produced by goldthioglucose.	1985-06-17	3924344
Transient monocular visual loss after aurothioglucose.	1985-06	3930722
The relationship between aurothioglucose- and D-penicillamine-induced proteinuria.	1984	6441248
Recovery from aplastic anemia secondary to gold salt therapy.	1977-09-01	334186
Comparative toxicity of gold preparations in treatment of rheumatoid arthritis.	1976-04	821403

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 Created by `admin` on `Mon Mar 31 21:25:18 GMT 2025` Edited by `admin` on `Mon Mar 31 21:25:18 GMT 2025`
Record UNII	2P2V9Q0E78
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AUROTHIOGLUCOSE

Common Name

English

AUREOTAN

Preferred Name

English

AUROTHIOGLUCOSE [MART.]

Common Name

English

GOLD, (1-(THIO-.KAPPA.S)-D-GLUCOPYRANOSATO-.KAPPA.O2)

Common Name

English

BRENOL

Brand Name

English

GLYSANOL B

Brand Name

English

AUROTHIOGLUCOSE [VANDF]

Common Name

English

AUROTHIOGLUCOSE [USP-RS]

Common Name

English

AURUMINE

Brand Name

English

AUTHRON

Brand Name

English

GOLD THIOGLUCOSE

Systematic Name

English

SOLGANAL

Brand Name

English

AUROTHIOGLUCOSE [IARC]

Common Name

English

AUROTHIOGLUCOSE [MI]

Common Name

English

ORONOL

Brand Name

English

AUROTHIOGLUCOSE [HSDB]

Common Name

English

NSC-759601

Code

English

(1-THIO-D-GLUCOPYRANOSATO)GOLD

Common Name

English

Aurothioglucose [WHO-DD]

Common Name

English

SOLGANAL B

Brand Name

English

AUROTHIOGLUCOSE [USP MONOGRAPH]

Common Name

English

GOLD, (1-THIO-D-GLUCOPYRANOSATO)-

Common Name

English

Classification Tree Code System Code

WHO-VATC

QM01CB04