Sodium aurothiomalate

Identification

Summary

Sodium aurothiomalate is a disease-modifying antirheumatic drug (DMARD) indicated for the symptomatic treatment of arthritis.

Generic Name
Sodium aurothiomalate
DrugBank Accession Number
DB09276
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 390.07
Monoisotopic: 389.921312
Chemical Formula
C4H3AuNa2O4S
Synonyms
  • Aurotiomalato sodico
  • Gold sodium thiomalate
  • Natrii aurothiomalas
  • Sodium aurothiomalate

Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofFelty's syndrome••••••••••••
Management ofJuvenile rheumatoid arthritis••••••••••••
Management ofPsoriatic arthritis••••••••••••
Management ofRheumatoid arthritis••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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

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.

Absorption

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

Volume of distribution

The apparent volume of distribution is 0.26 +/- 0.051 kg-1

Protein binding

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

Metabolism

No data available.

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.

Half-life

12.5 days

Clearance

7.0 ml/ kg/day

Adverse Effects
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Toxicity

Overdosage symptoms are those of heavy metal toxicity; they include pruritus, dermatitis, stomatitis, vague gastrointestinal discomfort, albuminuria with or without a nephrotic syndrome, hematuria, agranulocytosis, thrombocytopenic purpura, and aplastic anemia.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirThe metabolism of Abacavir can be decreased when combined with Sodium aurothiomalate.
AceclofenacAceclofenac may decrease the excretion rate of Sodium aurothiomalate which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Sodium aurothiomalate which could result in a higher serum level.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Sodium aurothiomalate.
AcetazolamideAcetazolamide may increase the excretion rate of Sodium aurothiomalate which could result in a lower serum level and potentially a reduction in efficacy.
Food Interactions
No interactions found.

Products

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Active Moieties
NameKindUNIICASInChI Key
Gold cation (1+)ionic3D8CUH9F2120681-14-5ZBKIUFWVEIBQRT-UHFFFAOYSA-N
International/Other Brands
Myocrisin
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MyochrysineSolution10 mg / mLIntramuscularSanofi Aventis1935-12-312019-06-04Canada flag
MyochrysineInjection50 mg/1mLIntramuscularAkorn2010-04-222012-01-01US flag
MyochrysineSolution25 mg / mLIntramuscularSanofi Aventis1935-12-312019-06-04Canada flag
MyochrysineSolution50 mg / mLIntramuscularSanofi Aventis1935-12-312019-06-04Canada flag
Sodium Aurothiomalate Injection BPSolution10 mg / mLIntramuscularSandoz Canada Incorporated2002-07-022019-08-01Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
MyochrysineSodium aurothiomalate (50 mg/1mL)InjectionIntramuscularAkorn2010-04-222012-01-01US flag

Categories

ATC Codes
M01CB01 — Sodium aurothiomalate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Thia fatty acids
Alternative Parents
Dicarboxylic acids and derivatives / Carboxylic acid salts / Organic transition metal salts / Carboxylic acids / Organosulfur compounds / Organic sodium salts / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid salt / Dicarboxylic acid or derivatives / Hydrocarbon derivative / Organic alkali metal salt / Organic oxide / Organic oxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
organic sodium salt (CHEBI:35864)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
HRS6S09A0H
CAS number
12244-57-4
InChI Key
VXIHRIQNJCRFQX-UHFFFAOYSA-K
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
IUPAC Name
disodium 2-(auriosulfanyl)butanedioate
SMILES
[Na+].[Na+].[O-]C(=O)CC(S[Au])C([O-])=O

References

General References
  1. Kean WF, Kean IR: Clinical pharmacology of gold. Inflammopharmacology. 2008 Jun;16(3):112-25. doi: 10.1007/s10787-007-0021-x. [Article]
  2. Jessop JD, O'Sullivan MM, Lewis PA, Williams LA, Camilleri JP, Plant MJ, Coles EC: A long-term five-year randomized controlled trial of hydroxychloroquine, sodium aurothiomalate, auranofin and penicillamine in the treatment of patients with rheumatoid arthritis. Br J Rheumatol. 1998 Sep;37(9):992-1002. [Article]
  3. product info [Link]
PubChem Compound
16760302
PubChem Substance
310265170
ChemSpider
20946
RxNav
4981
ChEBI
35864
Wikipedia
Sodium_aurothiomalate

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionIntramuscular50 mg
InjectionIntramuscular50 mg/1mL
SolutionIntramuscular10 mg / mL
SolutionIntramuscular25 mg / mL
SolutionIntramuscular50 mg / mL
SolutionIntramuscular40 mg/1ml
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility38.8 mg/mLALOGPS
logP-0.6ALOGPS
logP-0.11Chemaxon
logS-1ALOGPS
pKa (Strongest Acidic)3.18Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area80.26 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity51.78 m3·mol-1Chemaxon
Polarizability13.65 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [Article]

Drug created at October 28, 2015 22:28 / Updated at March 28, 2024 03:23