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Namespace Prefixes

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Statements

Subject Item
n2:DB00995
rdf:type
n3:Drug
n3:description
Auranofin is a organogold compound classified by the World Health Organization as an antirheumatic agent. Auranofin appears to induce heme oxygenase 1 (HO-1) mRNA. Heme oxygenase 1 is an inducible heme-degrading enzyme with anti-inflammatory properties.
n3:dosage
n16:271B4BDF-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Jeon KI, Byun MS, Jue DM: Gold compound auranofin inhibits IkappaB kinase (IKK) by modifying Cys-179 of IKKbeta subunit. Exp Mol Med. 2003 Apr 30;35(2):61-6. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12754408 # Kim IS, Jin JY, Lee IH, Park SJ: Auranofin induces apoptosis and when combined with retinoic acid enhances differentiation of acute promyelocytic leukaemia cells in vitro. Br J Pharmacol. 2004 Jun;142(4):749-55. Epub 2004 May 24. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15159275 # Venardos K, Harrison G, Headrick J, Perkins A: Auranofin increases apoptosis and ischaemia-reperfusion injury in the rat isolated heart. Clin Exp Pharmacol Physiol. 2004 May-Jun;31(5-6):289-94. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15191400 # Hafejee A, Winhoven S, Coulson IH: Jessner's lymphocytic infiltrate responding to oral auranofin. J Dermatolog Treat. 2004 Sep;15(5):331-2. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15370403 # Rigobello MP, Folda A, Baldoin MC, Scutari G, Bindoli A: Effect of auranofin on the mitochondrial generation of hydrogen peroxide. Role of thioredoxin reductase. Free Radic Res. 2005 Jul;39(7):687-95. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16036347
n3:group
approved
n3:indication
Used in the treatment of active, progressive or destructive forms of inflammatory arthritis, such as adult rheumatoid arthritis.
n3:manufacturer
n10:271B4BDD-363D-11E5-9242-09173F13E4C5
owl:sameAs
n14:DB00995 n19:DB00995
dcterms:title
Auranofin
adms:identifier
n7:Auranofin n11:65483-093-06 n12:PA448510 n17:D00237 n18:2922 n20:DB00995
n3:mechanismOfAction
Exactly how auranofin works is not well understood. It may act as an inhibitor of kappab kinase and thioredoxin reductase which would lead to a decreased immune response and decreased free radical production, respectively. In patients with inflammatory arthritis, such as adult and juvenile rheumatoid arthritis, gold salts can decrease the inflammation of the joint lining. This effect can prevent destruction of bone and cartilage.
n3:packager
n10:271B4BDA-363D-11E5-9242-09173F13E4C5 n10:271B4BDB-363D-11E5-9242-09173F13E4C5 n10:271B4BDC-363D-11E5-9242-09173F13E4C5
n3:routeOfElimination
Approximately 60% of the absorbed gold (15% of the administered dose) from a single dose of auranofin is excreted in urine; the remainder is excreted in the feces.
n3:synonym
(1-Thio-beta-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetate Auroafen Triethylphosphine gold Auranofine Auranofinum 2,3,4,6-Tetra-O-acetyl-1-thio-beta-D-glucopyranosato-S (triethylphosphine)gold Ridaura Auranofina
n3:toxicity
Oral, rat: LD<sub>50</sub> = > 2000 mg/kg. Symptoms of overdose may include diarrhoea, vomiting, abdominal cramps, and symptoms of hypersensitivity (such as skin rash, hives, itching, and difficulty breathing).
n4:hasAHFSCode
n5:60-00-00
n3:foodInteraction
Take with food to reduce irritation.
n3:synthesisReference
David T. Hill, Ivan Lantos, Blaine M. Sutton, "Process and intermediate for preparing auranofin." U.S. Patent US4133952, issued January, 1972.
n24:hasConcept
n25:M0001971
foaf:page
n23:auranofin.html n26:rid1379.shtml
n3:IUPAC-Name
n8:271B4BE4-363D-11E5-9242-09173F13E4C5
n3:InChI
n8:271B4BEA-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n8:271B4BE9-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n8:271B4BE6-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n8:271B4BE7-363D-11E5-9242-09173F13E4C5
n3:SMILES
n8:271B4BE8-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n8:271B4BE2-363D-11E5-9242-09173F13E4C5
n3:logP
n8:271B4BE3-363D-11E5-9242-09173F13E4C5 n8:271B4BE0-363D-11E5-9242-09173F13E4C5
n3:logS
n8:271B4BE1-363D-11E5-9242-09173F13E4C5
n4:hasATCCode
n21:M01CB03
n3:H-Bond-Acceptor-Count
n8:271B4BF0-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n8:271B4BF1-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n8:271B4BEB-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n8:271B4BEC-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n8:271B4BEE-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n8:271B4BED-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n8:271B4BEF-363D-11E5-9242-09173F13E4C5
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
34031-32-8
n3:category
n3:containedIn
n15:271B4BDE-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n8:271B4BF5-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n8:271B4BF7-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n8:271B4BF8-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n8:271B4BF9-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n8:271B4BF4-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n8:271B4BF3-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n8:271B4BF6-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n8:271B4BE5-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n8:271B4BF2-363D-11E5-9242-09173F13E4C5