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Aurothioglucose
Also known as: 12192-57-3, Gold(1+);3,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-thiolate, Gold(1+);(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-thiolate, Aurothioglucose hydrate, Ncgc00096015-01, Aurothioglucose 80%
Molecular Formula
C6H11AuO5S
Molecular Weight
392.18  g/mol
InChI Key
XHVAWZZCDCWGBK-BMZZJELJSA-M

A thioglucose derivative used as an antirheumatic and experimentally to produce obesity in animals.
1 2D Structure

Aurothioglucose

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
gold(1+);(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-thiolate
2.1.2 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
2.1.3 InChI Key
XHVAWZZCDCWGBK-BMZZJELJSA-M
2.1.4 Canonical SMILES
C(C1C(C(C(C(O1)[S-])O)O)O)O.[Au+]
2.1.5 Isomeric SMILES
C([C@@H]1[C@H]([C@@H]([C@H](C(O1)[S-])O)O)O)O.[Au+]
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Aureotan

2. Auromyose

3. Aurothioglucose, Beta D Isomer

4. Aurothioglucose, Beta-d Isomer

5. Aurothioglucose, Sodium Salt, Beta-d Isomer

6. B Oleosum, Solganal

7. Beta-d Isomer Aurothioglucose

8. Gold 50

9. Gold Thioglucose

10. Gold-50

11. Gold50

12. Oleosum, Solganal B

13. Solganal

14. Solganal B Oleosum

15. Solganol

16. Thioglucose, Gold

17. Thioglucosoaurate

2.2.2 Depositor-Supplied Synonyms

1. 12192-57-3

2. Gold(1+);3,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-thiolate

3. Gold(1+);(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-thiolate

4. Aurothioglucose Hydrate

5. Ncgc00096015-01

6. Aurothioglucose 80%

7. Spectrum_001866

8. Nsc-759601

9. Dsstox_cid_26013

10. Dsstox_rid_81289

11. Dsstox_gsid_46013

12. Kbioss_002383

13. Spectrum1500132

14. Kbio2_002379

15. Kbio2_004947

16. Kbio2_007515

17. Hms2091k17

18. Pharmakon1600-01500132

19. Tox21_111549

20. Nsc759601

21. Ccg-213700

22. Sbi-0206666.p002

23. Cas-12192-57-3

24. Ab00053375_02

25. 192a573

26. Sr-05000001568

27. Sr-05000001568-1

2.3 Create Date
2005-08-01
3 Chemical and Physical Properties
Molecular Weight 392.18 g/mol
Molecular Formula C6H11AuO5S
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count1
Exact Mass391.999290 g/mol
Monoisotopic Mass391.999290 g/mol
Topological Polar Surface Area91.2 Ų
Heavy Atom Count13
Formal Charge0
Complexity160
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Therapeutic Uses

... Aurothioglucose ... /is/ indicated in the treatment of adult or juvenile rheumatoid arthritis. ... /This agent is/ usually used for treating patients who show evidence of continued or additional disease activity despite conservative therapy, e.g., with salicylates (especially aspirin) or other nonsteroidal anti-inflammatory agents, glucocorticoids, etc. /Included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1586


Gold compounds are used in the treatment of these rheumatic conditions / psoriatic arthritis, Felty's syndrome/. /Gold compounds; NOT included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1587


4.2 Drug Warning

Patients intolerant of parabens may be intolerant of parenteral aurothioglucose, which may contain propylparaben.

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1587


Patients sensitive to sesame products may also be sensitive to the sesame oil vehicle of parenteral aurothioglucose.

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1587


Dermatitis is the most common reaction. Pruritus should be considered a warning signal of an impending cutaneous reaction. Erythema and occasionally the more severe reactions such as popular, vesicular, and exfoliative dermatitis leading to alopecia and shedding of the nails may occur. Chrysiasis (gray-to-blue pigmentation) has been reported, especially in photo-exposed areas. Gold dermatitis may be aggravated by exposure to sunlight, or an actinic rash may develop.

Medical Economics Co; Physicians Desk Reference 50th ed p. 2388 (1996)


Stomatitis is the second most common adverse reaction. Shallow ulcers on the buccal membranes, on the borders of the tongue and on the palate, diffuse glossitis , or gingivitis may be preceded by the sensation of metallic taste. Careful oral hygiene is recommended. Inflammation of the upper respiratory tract, pharyngitis, gastritis, colitis, tracheitis, and vaginitis have also been reported. Conjunctivitis is rare.

Medical Economics Co; Physicians Desk Reference 50th ed p. 2388 (1996)


For more Drug Warnings (Complete) data for AUROTHIOGLUCOSE (11 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antirheumatic Agents

Drugs that are used to treat RHEUMATOID ARTHRITIS. (See all compounds classified as Antirheumatic Agents.)


5.2 ATC Code

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01C - Specific antirheumatic agents

M01CB - Gold preparations

M01CB04 - Aurothioglucose


5.3 Absorption, Distribution and Excretion

The true potential of gold compounds, including ... aurothioglucose, to cumumulate has not been clearly defined, but it is clear that substantially larger amounts of gold are retained in the body during therapy with parenteral gold compounds than during therapy with auranofin.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 2848


Small amounts of gold have been shown to be distributed into milk in women receiving aurothioglucose ... .

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 2848


Gold is absorbed from injection sites, reaching peak concentration in blood in four to six hours. Following single intramuscular injection of 50 mg Solganal /aurothioglucose/ suspension in each of two patients, peak serum levels were about 235 mcg/dl in one patient and 450 mcg/dl in the other. In plasma, 95% is bound to albumin fraction. Approximately 70% of the gold is eliminated in the urine and approximately 30% in the feces. When a standard weekly treatment schedule is followed, approximately 40% of the administered dose is excreted each week, and the remainder is excreted over a longer period.

Medical Economics Co; Physicians Desk Reference 50th ed p. 2388 (1996)


After the initial injection, the serum level of gold rises sharply and declines over the next week. Peak levels with aqueous preparations are higher and decline faster than those with oily preparations. Weekly administration produces a continuous rise in the basal value for several months, after which the serum level becomes relatively stable. After a standard weekly dose, considerable individual variation in the levels of gold has been found. A steady decline in gold levels occurs when the interval between injections is lengthened, and small amounts may be found in the serum for months after discontinuance of therapy. The incidence of toxic reactions is apparently unrelated to the cumulative body content of gold.

Medical Economics Co; Physicians Desk Reference 50th ed p. 2388 (1996)


For more Absorption, Distribution and Excretion (Complete) data for AUROTHIOGLUCOSE (6 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

For a patient receiving gold sodium thiomalate the principal gold species in the urine is [Au(CN)2]-, which is also seen in a low molecular weight infiltrate of the blood. The same compound is also identified in the urine and blood of a patient taking solganol

PMID:8474063 Elder R et al; J Rheumatol. 20 (2): 268-72 (1993)


5.5 Biological Half-Life

The biological half-life of gold salts following a single 50 mg dose has been reported to range from 3 to 27 days. Following successive weekly doses, the half-life increases and may be 14 to 40 days after the third dose and up to 168 days after the eleventh weekly dose.

Medical Economics Co; Physicians Desk Reference 50th ed p. 2388 (1996)


5.6 Mechanism of Action

The effects of aurothioglucose, on basal and forskolin-activated adenylyl cyclase activity in human total lymphocyte membranes and in membranes of T and B lymphocyte subsets /was studied/. The gold compounds inhibited adenylyl cyclase activity. This inhibitory effect required the presence of both the sulfhydryl ligands and aurous cation. Regulation of lymphocyte adenylyl cyclase by gold compounds represents a potential mode of action of these drugs in rheumatic disease.

PMID:1642653 Lazarevic M et at; Arthritis Rheum 35 (8): 857-64 (1992)


Transcription factor NF-kappaB controls the expression of a number of genes including those for cell adhesion molecules such as E-selectin, ICAM- 1 and VCAM- 1. These cell adhesion molecules are known to play important roles in a critical step of tumor metastasis; the arrest of tumor cells on the venous or capillary bed of the target organ. NF-kappaB is activated by extracellular signals such as those elicited by the proinflammatory cytokines, TNF and IL-1. The adhesion of tumor cells to IL-1 beta-treated HUVEC /human umbilical vein endothelial cells/ was inhibited by gold compounds such as aurothioglucose.

Tozawa K et al; Cancer Lett. 196 (1): 93-100


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