Structure via PubChem · Public domain (PubChem)
auranofin
Sign in to saveAlso known as Ridaura®, SK&F-39162, SK-39162, Triethylphosphine gold, 2,3,4,6-Tetra-O-acetyl-1-thio-beta-D-glucopyranosato-S (triethylphosphine)gold, (1-Thio-beta-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetate, Auranofina, Auranofinum
Auranofin is an orally administered gold salt classified by the World Health Organization as an antirheumatic agent. It has the brand name Ridaura. Along with sodium aurothiomalate, it is one of only two gold compounds currently employed in modern medicine.
In the Vinony graph
Vinony's link graph records 74 inbound references to auranofin, and connects out to disease-modifying antirheumatic drug, gold monosodium thiomalate and aurothioglucose.
Vinony files it under Acetate esters, Antirheumatic products and Disease-modifying antirheumatic drugs.
Vinony links it to 17 Wikipedia language editions.
Chemical data
- Formula
- C20H34AuO9PS
- Molecular weight
- 678.5 g/mol
- IUPAC name
- gold(1+);(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxane-2-thiolate;triethylphosphane
- SMILES
- CCP(CC)CC.CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)[S-])OC(=O)C)OC(=O)C)OC(=O)C.[Au+]
- InChIKey
- AUJRCFUBUPVWSZ-XTZHGVARSA-M
- Polar surface area
- 115 Ų
- H-bond donors
- 0
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1985
- Admin. routes
- oral
- Indications
- rheumatoid arthritis, chronic lymphocytic leukemia, HIV infection, glioblastoma multiforme
via ChEMBL · EBI
Research
1,735 papers- Auranofin: Past to Present, and repurposing.International immunopharmacology · 2021
- Will Auranofin Become a Golden New Treatment Against COVID-19?Frontiers in immunology · 2021
- Auranofin.British journal of rheumatology · 1997
- Auranofin attenuates hepatic steatosis and fibrosis in nonalcoholic fatty liver disease via NRF2 and NF- κB signaling pathways.Clinical and molecular hepatology · 2022
- Potential Anticancer Activity of Auranofin.Chemical & pharmaceutical bulletin · 2019
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 678.132684
- Has use
- medication
Show 10 more facts
- route of administration
- oral administration
- Commons category
- Auranofin
- chemical formula
- C₂₀H₃₄AuO₉PS
- medical condition treated
- rheumatoid arthritis
- isomeric SMILES
- CCP(CC)CC.CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)[S-])OC(=O)C)OC(=O)C)OC(=O)C.[Au+]
- canonical SMILES
- CCP(CC)CC.CC(=O)OCC1C(C(C(C(O1)[S-])OC(=O)C)OC(=O)C)OC(=O)C.[Au+]
- World Health Organisation international non-proprietary name
- auranofin
- inhibitor of
- growth
- defined daily dose
- 6
- legal status (medicine)
- boxed warning
via Wikidata · CC0
~4 min read
Encyclopedic overview
13 sectionsContents
- Use
- Research
- HIV infection
- Amebiasis
- Acanthamoeba keratitis and primary amoebic meningoencephalitis
- Tuberculosis
- Ovarian cancer
- Lung cancers including adenocarcinoma
- COVID-19
- Etymology
- References
- Further reading
- External links
Auranofin is an orally administered gold salt classified by the World Health Organization as an antirheumatic agent. It has the brand name Ridaura. Along with sodium aurothiomalate, it is one of only two gold compounds currently employed in modern medicine.
==Use== Auranofin is used to treat rheumatoid arthritis. It improves arthritis symptoms including painful or tender and swollen joints and morning stiffness. Auranofin is a safer treatment compared to the more common injectable gold thiolates (gold sodium thiomalate and gold thioglucose), but meta-analysis of 66 clinical trials concluded that it is somewhat less effective.
Excerpted from Wikipedia’s “auranofin” article, available under the CC BY-SA 4.0 licence.