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	196.9666
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 In 2001, aurothioglucose was withdrawn from the Dutch market, where it had been the only injectable gold preparation available since 1943, forcing hospitals to change medication for a large number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 8297
Thioredoxin reductase 1 2 Target ID: CHEMBL1927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24295151	Inhibitor 8297	65.0 nM [IC50]
Glutathione peroxidase 1 1 Target ID: CHEMBL2163186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9685351	Inhibitor 8297	80.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2885986	Primary		Approved 8429	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 n = 3 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 35 to 86 years Sex: M+F Population Size: 3 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 n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 43 years Sex: F Population Size: 1 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 n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 56 years Sex: F Population Size: 1 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 Co-administed with:: sulphasalazine hydroxychloroquine Sources: https://pubmed.ncbi.nlm.nih.gov/1978639/	unhealthy, 56 years n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 56 years Sex: F Population Size: 1 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 n = 25 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: adult Sex: M+F Population Size: 25 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 n = 26 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: mean age 56 years Sex: M+F Population Size: 26 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	AP12192573	https://reagents.alfa-chemistry.com/product/aurothioglucose-cas-12192-57-3-2905.html
Alfa Chemistry	ALP12192573	https://reagents.alfa-chemistry.com/product/aurothioglucose-hydrate-cas-12192-57-3-anhydrous-56.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
BOC Sciences	12192-57-3	https://www.bocsci.com/aurothioglucose-cas-12192-57-3-item-84-55856.html
BioCrick	BCC5446	http://www.biocrick.com/Aurothioglucose-BCC5446.html
Glentham Life Sciences	GK8154	http://www.glentham.com/products/product/GK8154/
Molcore	MC512396	https://www.molcore.com/product/12192-57-3
OChem	15591	http://www.ocheminc.com/index.php?act=psearch&pid=192A573
eNovation Chemicals	D676617	https://www.enovationchem.com/ProductDetails.asp?ProductID=D676617
iChemical	EBD31793	http://www.ichemical.com/chemicals/cas-12192-57-3

PubMed

Title	Date	PubMed
Comparative toxicity of gold preparations in treatment of rheumatoid arthritis.	1976 Apr	821403
Recovery from aplastic anemia secondary to gold salt therapy.	1977 Sep-Oct	334186
The relationship between aurothioglucose- and D-penicillamine-induced proteinuria.	1984	6441248
Transient monocular visual loss after aurothioglucose.	1985 Jun	3930722
Glycolytic concomitant of brain inflammation produced by goldthioglucose.	1985 Jun 17	3924344
Thioglucose interactions with a "gold thioglucose-lesioned glucostat".	1985 Sep	3928877
Gold thioglucose selectively damages dorsal vagal nuclei.	1986 Mar 5	3084036
Effects of thioglucoses on sensitivity to insulin hypoglycemic convulsions.	1986 May	3084764
Sterile oily abscess from depot gold therapy.	1993 Nov	8240442
Thiol-reactive metal compounds inhibit NF-kappa B activation by blocking I kappa B kinase.	2000 Jun 1	10820281
Endogenous reductants support the catalytic function of recombinant rat cyt19, an arsenic methyltransferase.	2004 Mar	15025511
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 Oct	15990992
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 Apr	21382165
Substrate and inhibitor specificities differ between human cytosolic and mitochondrial thioredoxin reductases: Implications for development of specific inhibitors.	2011 Mar 15	21172426
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013 Sep 5	23769903

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 `Sat Dec 16 04:58:51 GMT 2023` Edited by `admin` on `Sat Dec 16 04:58:51 GMT 2023`
Record UNII	2P2V9Q0E78
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AUROTHIOGLUCOSE

Common 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

AUREOTAN

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