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    Also known as: Tauredon, Gold sodium thiomalate, 12244-57-4, Myocrisin, Chrysothios, Butanedioic acid, mercapto-, monogold(1+) sodium salt
    Molecular Formula
    C4H3AuNa2O4S
    Molecular Weight
    390.08  g/mol
    InChI Key
    VXIHRIQNJCRFQX-UHFFFAOYSA-K
    Gold Sodium Thiomalate
    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 2D Structure

    Gold Sodium Thiomalate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    disodium;gold(1+);2-sulfidobutanedioate
    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
    2.1.3 InChI Key
    VXIHRIQNJCRFQX-UHFFFAOYSA-K
    2.1.4 Canonical SMILES
    C(C(C(=O)[O-])[S-])C(=O)[O-].[Na+].[Na+].[Au+]
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Aurolate

    2. Aurothiomalate

    3. Aurothiomalate, Sodium

    4. Gold Disodium Thiomalate, Monohydrate

    5. Gold Sodium Thiomalate

    6. Gold Thiomalate

    7. Gold Thiomalate, Sodium

    8. Gold Thiomalic Acid

    9. Mercaptobutanedioic Acid Monogold(1+) Sodium Salt

    10. Miocrin

    11. Miocrisin

    12. Monogold (1+) Disodium Thiomalate

    13. Myochrysine

    14. Myocrisin

    15. Myocrysine

    16. Sodium Gold Thiomalate

    17. Sodium Thiomalate, Gold

    18. Sodium Thiomalatoaurate

    19. Tauredon

    20. Thiomalate, Gold

    21. Thiomalatoaurate, Sodium

    2.2.2 Depositor-Supplied Synonyms

    1. Tauredon

    2. Gold Sodium Thiomalate

    3. 12244-57-4

    4. Myocrisin

    5. Chrysothios

    6. Butanedioic Acid, Mercapto-, Monogold(1+) Sodium Salt

    7. Miochrysin

    8. Myocrisine

    9. Kidon

    10. Taure(o)don

    11. Disodium Aurothiomalate

    12. Aurothiomala-natrium

    13. Aurothiomalate Sodium

    14. Aurothiomalato Sodico

    15. Aurotiomalato Sodico

    16. Natrii Aurothiomalas

    17. Dinatrium 2-(aurothio)succinat

    18. Hsdb 7173

    19. Natrii Aurothiomalas [inn-latin]

    20. Aurothiomalate De Sodium

    21. Aurotiomalato Sodico [inn-spanish]

    22. Disodium;gold(1+);2-sulfidobutanedioate

    23. Einecs 235-479-7

    24. Aurothiomalate De Sodium [inn-french]

    25. Unii-e4768zy6gm

    26. Succinic Acid, Mercapto-, Gold Sodium Salt

    27. Disodium [2-(sulfanyl-kappas)butanedioato(3-)]aurate(2-)

    28. Gold Sodium Thiomalate [usan:usp]

    29. Na2[au(thiomalate)]

    30. Sodium Aurothiomalate(i)

    31. Sodium Aurum(i) Thiomalate

    32. Schembl8548

    33. Sodium Aurothiomalate [inn]

    34. Disodium Thiomalato-s-gold(i)

    35. E4768zy6gm

    36. Disodium Thiomalato-s-aurate(i)

    37. Chebi:35864

    38. Mfcd00064304

    39. Db09276

    40. Sodium (1,2-dicarboxylatoethylthio)gold

    41. [(1,2-dicarboxyethyl)thio]gold Disodium Salt

    42. Mercaptobutanedioic Acid Gold(i) Disodium Salt

    2.3 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 390.08 g/mol
    Molecular Formula C4H3AuNa2O4S
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count1
    Exact Mass389.921313 g/mol
    Monoisotopic Mass389.921313 g/mol
    Topological Polar Surface Area81.3 Ų
    Heavy Atom Count12
    Formal Charge0
    Complexity126
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count4
    4 Drug and Medication Information
    4.1 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

    4.2 Drug Warning

    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.

    4.3 Drug Indication

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

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

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

    5.2 MeSH Pharmacological Classification

    Antirheumatic Agents

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

    5.3 ATC Code

    M - Musculo-skeletal system

    M01 - Antiinflammatory and antirheumatic products

    M01C - Specific antirheumatic agents

    M01CB - Gold preparations

    M01CB01 - Sodium aurothiomalate

    5.4 Absorption, Distribution and Excretion

    Absorption

    Gold sodium thiomalate solutions are rapidly absorbed following IM injection, with peak serum concentrations occurring in 3-6 hours.

    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

    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

    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.

    5.5 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

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

    5.6 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...

    PMID:6430362 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...

    PMID:3150043 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. ...

    PMID:6430362 Massarella J et al; Biopharm Drug Dispos 5 (2): 101-7 (1984)

    5.7 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.

    PMID:1642653 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

    PMID:10583116 Rasanen L, et al; Br J Dermatol 141 (4): 683-8 (1999)

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