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Gold sodium thiomalate

PubChem CID
6093241
Structure
Gold sodium thiomalate_small.png
Gold sodium thiomalate_3D_Structure.png
Molecular Formula
Synonyms
  • Gold disodium thiomalate
  • Sodium aurothiomalate
  • 74916-57-7
  • UNII-HRS6S09A0H
  • 12244-57-4
Molecular Weight
390.08 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2006-03-13
  • Modify:
    2025-01-04
Description
Sodium aurothiomalate is a gold compound that is used for its immunosuppressive anti-rheumatic effects. Gold Sodium Thiomalate is supplied as a solution for intramuscular injection containing 50 mg of Gold Sodium Thiomalate per mL. It is most effective in active progressive rheumatoid arthritis and of little or no value in the presence of extensive deformities or in the treatment of other forms of arthritis.
Gold Sodium Thiomalate is the sodium salt of gold thiomalic acid, an organogold compound with antirheumatic and potential antineoplastic activities. Gold sodium thiomalate (GST) appears to inhibit the activity of atypical protein kinase C iota (PKCiota) by forming a cysteinyl-aurothiomalate adduct with the cysteine residue Cys-69 within the PB1 binding domain of PKCiota. This prevents the binding of Par6 (Partitioning defective protein 6) to PKCiota, thereby inhibiting PKCiota-mediated oncogenic signaling, which may result in the inhibition of tumor cell proliferation, the promotion of tumor cell differentiation, and the induction of tumor cell apoptosis. Atypical PKCiota, a serine/threonine kinase overexpressed in numerous cancer cell types, plays an important role in cancer proliferation, invasion, and survival; Par6 is a scaffold protein that facilitates atypical PKC-mediated phosphorylation of cytoplasmic proteins involved in epithelial and neuronal cell polarization.
A variable mixture of the mono- and disodium salts of gold thiomalic acid used mainly for its anti-inflammatory action in the treatment of rheumatoid arthritis. It is most effective in active progressive rheumatoid arthritis and of little or no value in the presence of extensive deformities or in the treatment of other forms of arthritis.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Gold sodium thiomalate.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

disodium;gold(1+);2-sulfidobutanedioate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C4H6O4S.Au.2Na/c5-3(6)1-2(9)4(7)8;;;/h2,9H,1H2,(H,5,6)(H,7,8);;;/q;3*+1/p-3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

VXIHRIQNJCRFQX-UHFFFAOYSA-K
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C(C(C(=O)[O-])[S-])C(=O)[O-].[Na+].[Na+].[Au+]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C4H3AuNa2O4S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

12244-57-4
74916-57-7

2.3.2 Deprecated CAS

185826-27-1; 1096140-34-9

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 DrugBank ID

2.3.6 DSSTox Substance ID

2.3.7 Metabolomics Workbench ID

2.3.8 NCI Thesaurus Code

2.3.9 Nikkaji Number

2.3.10 Wikidata

2.3.11 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Aurolate
  • Aurothiomalate
  • Aurothiomalate, Sodium
  • Gold Disodium Thiomalate, Monohydrate
  • Gold Sodium Thiomalate
  • Gold Thiomalate
  • Gold Thiomalate, Sodium
  • Gold Thiomalic Acid
  • Mercaptobutanedioic Acid Monogold(1+) Sodium Salt
  • Miocrin
  • Miocrisin
  • Monogold (1+) Disodium Thiomalate
  • Myochrysine
  • Myocrisin
  • Myocrysine
  • Sodium Aurothiomalate
  • Sodium Gold Thiomalate
  • Sodium Thiomalate, Gold
  • Sodium Thiomalatoaurate
  • Tauredon
  • Thiomalate, Gold
  • Thiomalatoaurate, Sodium

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
390.08 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
389.921313 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
389.921313 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
81.3Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
12
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
122
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
4
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Color / Form

White to yellowish-white powder; mixture of mono- and disodium salts
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 805

3.2.2 Odor

Odorless
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 548

3.2.3 Taste

Metallic taste
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 805

3.2.4 Solubility

Very soluble in water; practically insoluble in alcohol, ether
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 805

3.2.5 Stability / Shelf Life

Following the date of manufacture, ... gold sodium thiomalate injection /has an expiration date/ of 5 years.
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 2849

3.2.6 Other Experimental Properties

Aqueous solutions are colorless to pale yellow; pH of 5% aq solution: 5.8-6.5
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 805
Affected by light
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 548

3.3 Chemical Classes

3.3.1 Drugs

3.3.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Antirheumatic Agents

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug Indication

A disease-modifying antirheumatic drug (DMARD) indicated for the symptomatic treatment of arthritis.

6.2 Drug Classes

Breast Feeding; Lactation; Milk, Human; Antirheumatic Agents

6.3 Clinical Trials

6.3.1 ClinicalTrials.gov

6.3.2 EU Clinical Trials Register

6.4 Therapeutic Uses

... Gold sodium thiomalate ... /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

6.5 Drug Warnings

Patients with an impaired sulfoxidation ability (decreased ability to oxidize sulfhydryl-containing compounds) may be predisposed to ... /gold sodium thiomalate/ toxicity.
Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 1557
Vasomotor rections follow injections within minutes to hours and consist of weakness, dizziness, nausea, sweating and flushing, frequently accompanied by hypotension. Slower onset reactions consist of an exacerbation of joint pain and swelling, fatigue, and malaise that usually occur 6-24 hr after injection.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V2 160
Dermatitis is the most common reaction. Any eruption, especially if pruritic, that develops with treatment with myochrysine should be considered a reaction to gold until proven otherwise. Pruritus often exists before dermatitis becomes apparent, and there fore should be considered a warning signal of impending cutaneous reaction. The most serious form of cutaneous reaction is generalized exfoliative dermatitis which may lead to alopecia and shedding of nails. Gold dermatitis may be aggravated by exposure to sunlight or an actinic rash may develop.
Medical Economics Co; Physicians Desk Reference 50th ed p.1711 (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, or on the pharynx may occur as the only adverse reaction, or along with dermatitis. Sometimes diffuse glossitis or gingivitis develops. A metallic taste may precede these oral mucous membrane reactions and should be considered a warning signal.
Medical Economics Co; Physicians Desk Reference 50th ed p.1711 (1996)
For more Drug Warnings (Complete) data for GOLD SODIUM THIOMALATE (11 total), please visit the HSDB record page.

7 Pharmacology and Biochemistry

7.1 Pharmacodynamics

Unknown, may decrease prostaglandin synthesis or may alter cellular mechanisms by inhibiting sulfhydryl systems.

7.2 MeSH Pharmacological Classification

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

7.3 ATC Code

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01C - Specific antirheumatic agents

M01CB - Gold preparations

M01CB01 - Sodium aurothiomalate

7.4 Absorption, Distribution and Excretion

Absorption
Gold sodium thiomalate solutions are rapidly absorbed following IM injection, with peak serum concentrations occurring in 3-6 hours.
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
Route of Elimination
The major route of elimination of an IV dose of gold sodium thiomalate is urinary excretion, with a mean of 35% of the dose found in the urine in ten days. Fecal elimination accounts for an additional 9.4% of the IV dose excreted in ten days, probably as a result of biliary secretion.
Volume of Distribution
The apparent volume of distribution is 0.26 +/- 0.051 kg-1
Clearance
7.0 ml/ kg/day
Higher tissue levels occur with parenteral gold salts, with a mean steady state plasma level of 1 to 5 ug/ml. Drug is distributed widely throughout the body in lymph nodes, bone marrow, kidneys, liver, spleen, and tissues. About 85% to 90% is protein-bound.
Olson, K.R. (ed.) Poisoning & Drug Overdose. 3rd edition. Lange Medical Books/McGraw-Hill, New York, NY. 1999., p. 621
Gold has been shown to cross the placenta in pregnant women receiving gold sodium thiomalate. Small amounts of gold have been shown to be distributed into milk in women receiving ... gold sodium thiomalate.
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
Following single 10-mg doses of gold sodium thiomalate, serum gold concentrations showed a biphasic decline with a relatively rapid early phase (serum half-life about 43 hours) and a slow late phase (serum half-life about 6 days). The slow phase of decline may result from excretion and the rapid phase of decline may result from tissue distribution. The true potential of gold compounds, including ... gold sodium thiomalate, to cumulate 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
For more Absorption, Distribution and Excretion (Complete) data for GOLD SODIUM THIOMALATE (8 total), please visit the HSDB record page.

7.5 Metabolism / Metabolites

No data available.
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
Elder R et al; J Rheumatol. 20 (2): 268-72 (1993)

7.6 Biological Half-Life

12.5 days
Following single 10-mg doses of gold sodium thiomalate, serum gold concentrations showed a biphasic decline with a relatively rapid early phase (serum half-life about 43 hours) and a slow late phase (serum half-life about 6 days).
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
...Terminal log-linear phases corresponded to a mean disposition half-life of 25 days...
Massarella J et al; Biopharm Drug Dispos 5 (2): 101-7 (1984)
... the mean alpha half-lives were 0.738 and 1.78 hr for the iv and im routes, respectively. The corresponding terminal (beta) half-lives were 54.1 and 63.0 hr...
Melethil S et al; Pharm Res 4(4): 332-6 (1987)
Four normal male volunteers participated in a study designed to examine the disposition of gold given intramuscularly as gold sodium thiomalate. Blood samples were collected for 32 days following the administration of 10 mg of gold sodium thiomalate. .... Terminal log-linear phases corresponded to a mean disposition half-life of 25 days. ...
Massarella J et al; Biopharm Drug Dispos 5 (2): 101-7 (1984)

7.7 Mechanism of Action

The precise mechanism of action is unknown. It is known that sodium aurothiomalate inhibits the synthesis of prostaglandins. The predominant action appears to be a suppressive effect on the synovitis of active rheumatoid disease.
...The effects of aurothiomalate, 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.
Lazarevic M et al; 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 aurothiomalate.
Tozawa K et al; Cancer Letters 196 (1): 93-100
Gold dermatosis is mediated, at least in part, by allergic mechanisms
Rasanen L, et al; Br J Dermatol 141 (4): 683-8 (1999)

8 Use and Manufacturing

8.1 Uses

MEDICATION
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 805

8.2 Methods of Manufacturing

... A solution of thiomalic acid and 3 equivalents of sodium hydroxide are mixed with an aqueous suspension of gold(I)iodide. The product, a mixture of the mono- and disodium salts, is precipitated by the addition of ethanol.
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present, p. V3 540 (2003)

8.3 Formulations / Preparations

Parenteral: Injection, for IM use only, 50 mg/ml; Aurolate (with benzyl alcohol 0.5%), Taylor
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 2849
Myochrysine is supplied as a solution for intramuscular injection containing 50 mg of gold sodium thiomalate per ml.
Medical Economics Co; Physicians Desk Reference 50th ed p.1711 (1996)

9 Identification

9.1 Analytic Laboratory Methods

Analyte: gold sodium thiomalate; matrix: chemical identification; procedure: visual reaction (white precipitate) with calcium nitrate, nitric acid, and ammonium acetate
U.S. Pharmacopeia. The United States Pharmacopeia, USP 26/The National Formulary, NF 21; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p871 (2003)
Analyte: gold sodium thiomalate; matrix: chemical identification; procedure: visual reaction (yellow precipitate) with silver nitrate and ammonium hydroxide
U.S. Pharmacopeia. The United States Pharmacopeia, USP 26/The National Formulary, NF 21; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p871 (2003)
Analyte: gold sodium thiomalate; matrix: chemical identification; procedure: visual reaction with ammonium hydroxide and hydrogen peroxide, and evaporation resulting in particles of gold
U.S. Pharmacopeia. The United States Pharmacopeia, USP 26/The National Formulary, NF 21; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p871 (2003)
Analyte: gold sodium thiomalate; matrix: chemical purity; procedure: dissolve in water, filter, react with nitric and sulfuric acids, heat, cool, react with hydrogen peroxide, heat, cool, filter, dry, weigh residue
U.S. Pharmacopeia. The United States Pharmacopeia, USP 26/The National Formulary, NF 21; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p871 (2003)
For more Analytic Laboratory Methods (Complete) data for GOLD SODIUM THIOMALATE (7 total), please visit the HSDB record page.

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 2
View All
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Precautionary Statement Codes

P261, P264, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P333+P317, P362+P364, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 6 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Skin Sens. 1 (100%)

10.2 Accidental Release Measures

10.2.1 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

10.3 Handling and Storage

10.3.1 Storage Conditions

... Gold sodium thiomalate injection should be protected from light and stored at a temperature less than 40C, preferably at 1530C; freezing should be avoided.
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

10.4 Other Safety Information

Chemical Assessment

IMAP assessments - Butanedioic acid, mercapto-, monogold(1+) sodium salt: Human health tier I assessment

IMAP assessments - Butanedioic acid, mercapto-, monogold(1+) sodium salt: Environment tier I assessment

11 Toxicity

11.1 Toxicological Information

11.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Excretion of gold into milk after gold sodium thiomalate has not been rigorously studied. Case reports indicate that gold appears in milk in small quantities and at least a little of it is absorbed because it is detectable in the infant's urine. No convincing cases of toxicity have been reported. Monitoring for possible adverse effects in the breastfed infant would seem prudent. Opinions of authors of review articles vary from recommending avoidance to allowing use. Since gold salts are rarely used any longer, an alternative is preferred.

◉ Effects in Breastfed Infants

Four infants reportedly have been breastfed during maternal gold therapy (including gold sodium thiomalate and gold aurothioglucose). Transient facial edema occurred in an 18-month-old infant, 3 months after the mother's treatment stopped. The reaction was possibly due to gold in the mother's milk ingested by the infant.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

11.1.2 Antidote and Emergency Treatment

When severe reactions to gold occur, corticosteroids, dimercaprol (a chelating agent), or penicillamine may be given to aid recovery. Prednisone ... is recommended to manage severe renal, hematologic, pulmonary, or enterocolic reactions to gold. Dimercaprol may be used together with corticosteroids to facilitate removal of the gold when corticosteroid treatment alone is ineffective.
Olson, K.R. (ed.) Poisoning & Drug Overdose. 3rd edition. Lange Medical Books/McGraw-Hill, New York, NY. 1999., p. 621
Treatment with myochrysine /gold sodium thiomalate/ should be discontinued immediately when toxic reactions occur. Minor complications such as localized dermatitis, mild stomatitis or slight proteinuria generally require no other therapy and resolve spontaneously with suspension of myochrysine /gold sodium thiomalate/. Moderately severe skin and mucous membrane reactions often benefit from topical corticosteroids, oral antihistaminics, and soothing or anesthetic lotions.
Medical Economics Co; Physicians Desk Reference 50th ed p.1711 (1996)
For serious renal, hematologic, pulmonary, and enterocolitic complications, high doses of systemic corticosteroids are recommended. The optimum duration of corticosteroid treatment varies with response of the individual patient. Therapy may be required for many months when adverse effects are unusually severe or progressive.
Medical Economics Co; Physicians Desk Reference 50th ed p.1711 (1996)
In patients whose complications do not improve with high dose corticosteroid treatment, or who develop significant steroid related adverse reactions, a chelating agent may be given to enhance gold excretion. Dimercaprol (BAL) has been used successfully, but patients must be monitored carefully as numerous untoward reactions may attend it use. Corticosteroids and chelating agents may be used concomitantly.
Medical Economics Co; Physicians Desk Reference 50th ed p.1711 (1996)
For more Antidote and Emergency Treatment (Complete) data for GOLD SODIUM THIOMALATE (7 total), please visit the HSDB record page.

11.1.3 Medical Surveillance

Blood dyscrasia due to gold toxicity is rare, but because of the potential serious consequences it must be constantly watched for and recognized early by frequent blood examinations done throughout treatment. granulocytopenia, thrombocytopenia with or without purpura, eosinophilia, and hypoplastic and aplastic anemia, have been reported. These reactions may occur separately of in combinations.
Medical Economics Co; Physicians Desk Reference 50th ed p.1711 (1996)

11.1.4 Human Toxicity Excerpts

/CASE REPORTS/ A 53-year-old male was accidentally injected with an intramuscular dose of 450 mg of ... /gold sodium thiomalate/. Palpebral edema and rash were observed within 30 minutes. The blood gold levels reach 2970 ug/dlL without significant toxicity. The patient was treated with BAL (British anti-lewisite) and recovered.
Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 1557
/HUMAN EXPOSURE STUDIES/ .../The authors/ investigated whether allergic mechanisms are involved in dermatosis induced by gold sodium thiomalate (GSTM). Thirteen gold dermatosis patients, 15 arthritis patients without any side-effects from GSTM and 11 healthy controls participated in the study. Venous blood lymphocytes from these subjects were cultured with GSTM and gold sodium thiosulfate (GSTS) in the lymphocyte proliferation test (LPT). In some cases, interferon-gamma-producing cells were enumerated in vitro (T-cell ELISpot). The subjects were also patch-tested with GSTM and GSTS. The LPT to either GSTM, GSTS or both was positive in 12 of 13 patients with gold dermatosis. In the arthritis patient group without side-effects from gold, the LPT gave two false-positive results and in the healthy control group the LPT was falsely positive with one subject. T-cell ELISpot was positive in four of six gold dermatosis patients and negative in the arthritis and healthy control groups. Only one patient who also developed contact dermatitis from gold jewelry was positive to gold in the patch test.
Rasanen L, et al; Br J Dermatol 141 (4): 683-8 (1999)
/SIGNS AND SYMPTOMS/ Dermatitis is the most common reaction. Any eruption, especially if pruritic, that develops with treatment with myochrysine should be considered a reaction to gold until proven otherwise. Pruritus often exists before dermatitis becomes apparent, and there fore should be considered a warning signal of impending cutaneous reaction. The most serious form of cutaneous reaction is generalized exfoliative dermatitis which may lead to alopecia and shedding of nails. Gold dermatitis may be aggravated by exposure to sunlight or an actinic rash may develop.
Medical Economics Co; Physicians Desk Reference 50th ed p.1711 (1996)
/SIGNS AND SYMPTOMS/ Stomatitis is the second most common adverse reaction. Shallow ulcers on the buccal membranes, on the borders of the tongue and on the palate, or on the pharynx may occur as the only adverse reaction, or along with dermatitis. Sometimes diffuse glossitis or gingivitis develops. A metallic taste may precede these oral mucous membrane reactions and should be considered a warning signal.
Medical Economics Co; Physicians Desk Reference 50th ed p.1711 (1996)
For more Human Toxicity Excerpts (Complete) data for GOLD SODIUM THIOMALATE (6 total), please visit the HSDB record page.

11.1.5 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ ... Gold sodium thiomalate (AuTM) ...administered to Sprague-Dawley rats and three strains of mice, Swiss-Webster, C3H/HeJ, and DBA/2J, was studied with regard to its effect on liver and renal monooxygenases, metallothionein contents, and serum levels of alanine aminotransferase and urea nitrogen...Benzo(a)pyrene hydroxylase and benzphetamine N-demethylase activities were not altered by AuTM in livers of rats and the three strains of mice. Benzo(a)pyrene hydroxylase activity was significantly decreased in rat kidney, whereas this enzyme activity was not affected in the kidneys of mice. In rats, AuTM caused a sevenfold induction in liver metallothionein, while in mice, liver metallothionein was induced twofold in Swiss-Webster mice and about fivefold in the inbred strains. AuTM caused minimal changes in renal metallothionein contents in the three strains of mice studied. Serum alanine amino-transferase, an indicator of hepatotoxicity, was not altered by AuTM in rats and mice studied. Blood urea nitrogen, an indicator of kidney dysfunction, was increased threefold in rats, but not in AuTM-treated mice. These data demonstrate that AuTM, a nephrotoxic agent in rats and humans, showed no nephrotoxic effects in the mouse strains studied here.
Cheriathundam E, Alvares AP; J Biochem Toxicol 11 (4): 175-81 (1996)
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ... A modest nephrosis in rats following ip administration of aurothiomalate can be induced and is manifested by polyuria and proteinuria. These symptoms rapidly subside following treatment, although histological signs of permanent injury are evident several weeks later. /Aurothiomalate/
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V2 154
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Sodium aurothiomalate (monogold monosodium mono-hydrogen sulfidobutanedioate/, gold sodium thiomalate)/, an anti-rheumatoid gold agent, was injected s.c. every other day for three times or given in drinking water daily for two weeks to Balb/C mice that were inoculated with syngeneic Meth/A cells i.p. ...Statistically significant effects on survivals were obtained by 30 mg/kg/day s.c. or 75 mg/kg/day p.o. of gold. A dose of less than 12.5 mg/kg/day s.c. adversely affected the survival /of the animals/. ... No significant toxicity of gold was observed at doses up to 125 mg/kg/day.
Kamei H, et al; Cancer Biother Radiopharm 13 (5): 403-6 (1998)
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ studies in inbred mice have also demonstrated that that chronic treatment with disodium gold (I) thiomalate produced immune response to gold (III) in all A.SW mice, in about 70% of C57 BL/6 mice, and in none of the DBA/2 mice, clearly implicating genetic factors. These studies demonstrated that the strong immune response elicited were directed towards the gold (III) compounds, AuCl3 and HAuCl4, and that these dose-dependant responses were both T cell dependant and specific. It appears that in order to induce T cell sensitization, gold has to exist in the Au (III) state. Au (III) is a powerful thiol oxidizer and protein cross-linker, and in all likelihood, it is in this capacity that Au (III) alters proteins to create the final epitope(s) that are seen by responding T cells. /Gold sodium thiomalate/
Merchant B; Biologicals 26 (1): 49-59 (1998)
For more Non-Human Toxicity Excerpts (Complete) data for GOLD SODIUM THIOMALATE (6 total), please visit the HSDB record page.

11.1.6 Protein Binding

About 85-90% of the drug is protein bound.

11.2 Ecological Information

11.2.1 Milk Concentrations

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

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Chemical Co-Occurrences in Literature

12.4 Chemical-Gene Co-Occurrences in Literature

12.5 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Chemical Co-Occurrences in Patents

13.2 Chemical-Disease Co-Occurrences in Patents

13.3 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

14.2 Drug-Drug Interactions

15 Classification

15.1 MeSH Tree

15.2 WHO ATC Classification System

15.3 ChemIDplus

15.4 UN GHS Classification

15.5 EPA DSSTox Classification

15.6 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    Butanedioic acid, mercapto-, monogold(1+) sodium salt
    https://services.industrialchemicals.gov.au/search-assessments/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. EPA DSSTox
    Gold(1+) sodium 2-sulfidobutanedioate (1:2:1)
    https://comptox.epa.gov/dashboard/DTXSID80872500
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Hazardous Substances Data Bank (HSDB)
  8. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  9. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  10. Drugs and Lactation Database (LactMed)
  11. EU Clinical Trials Register
  12. Japan Chemical Substance Dictionary (Nikkaji)
  13. Metabolomics Workbench
  14. WHO Anatomical Therapeutic Chemical (ATC) Classification
    LICENSE
    Use of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.
    https://www.whocc.no/copyright_disclaimer/
  15. Wikidata
  16. Wikipedia
  17. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  18. PubChem
  19. GHS Classification (UNECE)
  20. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS