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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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Felty's syndrome •••••••••••• Management of Juvenile rheumatoid arthritis •••••••••••• Management of Psoriatic arthritis •••••••••••• Management of Rheumatoid 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir The metabolism of Abacavir can be decreased when combined with Sodium aurothiomalate. Aceclofenac Aceclofenac may decrease the excretion rate of Sodium aurothiomalate which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Sodium aurothiomalate which could result in a higher serum level. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Sodium aurothiomalate. Acetazolamide Acetazolamide 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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Active Moieties
Name Kind UNII CAS InChI Key Gold cation (1+) ionic 3D8CUH9F21 20681-14-5 ZBKIUFWVEIBQRT-UHFFFAOYSA-N - International/Other Brands
- Myocrisin
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Myochrysine Solution 10 mg / mL Intramuscular Sanofi Aventis 1935-12-31 2019-06-04 Canada Myochrysine Injection 50 mg/1mL Intramuscular Akorn 2010-04-22 2012-01-01 US Myochrysine Solution 25 mg / mL Intramuscular Sanofi Aventis 1935-12-31 2019-06-04 Canada Myochrysine Solution 50 mg / mL Intramuscular Sanofi Aventis 1935-12-31 2019-06-04 Canada Sodium Aurothiomalate Injection BP Solution 10 mg / mL Intramuscular Sandoz Canada Incorporated 2002-07-02 2019-08-01 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Myochrysine Sodium aurothiomalate (50 mg/1mL) Injection Intramuscular Akorn 2010-04-22 2012-01-01 US
Categories
- ATC Codes
- M01CB01 — Sodium aurothiomalate
- Drug Categories
- Acids, Acyclic
- Antiinflammatory and Antirheumatic Products
- Antirheumatic Agents
- Dicarboxylic Acids
- Drugs that are Mainly Renally Excreted
- Gold Compounds
- Gold Preparations
- Malates
- Musculo-Skeletal System
- Organogold Compounds
- Organometallic Compounds
- Specific Antirheumatic Agents
- Sulfhydryl Compounds
- Sulfur Compounds
- Thiomalates
- UGT1A1 Inhibitors
- 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
- Kean WF, Kean IR: Clinical pharmacology of gold. Inflammopharmacology. 2008 Jun;16(3):112-25. doi: 10.1007/s10787-007-0021-x. [Article]
- 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]
- product info [Link]
- External Links
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Completed Treatment Lung Cancer 1 1 Withdrawn Treatment Lung Cancer, Nonsmall Cell, Stage IIIA / Recurrent Non-small Cell Lung Cancer / Squamous Cell Lung Cancer / Stage IIIB Non-Small Cell Lung Cancer / Stage IV Non-small Cell Lung Cancer (NSCLC) / Unspecified Adult Solid Tumor, Protocol Specific 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Intramuscular 50 mg Injection Intramuscular 50 mg/1mL Solution Intramuscular 10 mg / mL Solution Intramuscular 25 mg / mL Solution Intramuscular 50 mg / mL Solution Intramuscular 40 mg/1ml - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 38.8 mg/mL ALOGPS logP -0.6 ALOGPS logP -0.11 Chemaxon logS -1 ALOGPS pKa (Strongest Acidic) 3.18 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 80.26 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 51.78 m3·mol-1 Chemaxon Polarizability 13.65 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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
- 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