Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H34AuO9PS |
Molecular Weight | 678.484 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[P](CC)(CC)[Au+][S-][C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O
InChI
InChIKey=IRPYFWIZKIOHQN-XTZHGVARSA-N
InChI=1S/C14H20O9S.C6H15P.Au/c1-6(15)19-5-10-11(20-7(2)16)12(21-8(3)17)13(14(24)23-10)22-9(4)18;1-4-7(5-2)6-3;/h10-14,24H,5H2,1-4H3;4-6H2,1-3H3;/t10-,11-,12+,13-,14+;;/m1../s1
Auranofin (brand name Ridaura) is an organogold compound classified by the World Health Organization as an antirheumatic agent. Ridaura is indicated in the management of adults with active classical or definite rheumatoid arthritis (ARA criteria) who have had an insufficient therapeutic response to, or are intolerant of, an adequate trial of full doses of one or more nonsteroidal anti-inflammatory drugs. The mechanism of action of is not understood. In patients with adult rheumatoid arthritis, it may modify disease activity as manifested by synovitis and associated symptoms, and reflected by laboratory parameters such as ESR. There is no substantial evidence, however, that gold-containing compounds induce remission of rheumatoid arthritis. 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. Ridaura should be added to a comprehensive baseline program, including non-drug therapies. Unlike anti-inflammatory drugs, RIDAURA does not produce an immediate response. Therapeutic effects may be seen after three to four months of treatment, although improvement has not been seen in some patients before six months.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1991 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17034761 |
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Target ID: P30044|||Q9UJU4 Gene ID: 25824.0 Gene Symbol: PRDX5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16036347 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | RIDAURA Approved UseRIDAURA (auranofin) is indicated in the management of adults with active classical or definite rheumatoid arthritis (ARA criteria) who have had an insufficient therapeutic response to, or are intolerant of, an adequate trial of full doses of one or more nonsteroidal anti-inflammatory drugs. RIDAURA should be added to a comprehensive baseline program, including non-drug therapies. Unlike anti-inflammatory drugs, RIDAURA does not produce an immediate response. Therapeutic effects may be seen after three to four months of treatment, although improvement has not been seen in some patients before six months. When cartilage and bone damage has already occurred, gold cannot reverse structural damage to joints caused by previous disease. The greatest potential benefit occurs in patients with active synovitis, particularly in its early stage. In controlled clinical trials comparing RIDAURA with injectable gold, RIDAURA was associated with fewer dropouts due to adverse reactions, while injectable gold was associated with fewer dropouts for inadequate or poor therapeutic effect. Physicians should consider these findings when deciding on the use of RIDAURA in patients who are candidates for chrysotherapy. Launch Date4.85740806E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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0.312 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27821451 |
6 mg 1 times / day multiple, oral dose: 6 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AURANOFIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.05 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27821451 |
6 mg 1 times / day multiple, oral dose: 6 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AURANOFIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
844 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27821451 |
6 mg 1 times / day multiple, oral dose: 6 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AURANOFIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
3 mg 2 times / day multiple, oral Recommended Dose: 3 mg, 2 times / day Route: oral Route: multiple Dose: 3 mg, 2 times / day Sources: Page: p.1310 |
unhealthy, 22-76 n = 72 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 22-76 Sex: M+F Population Size: 72 Sources: Page: p.1310 |
Disc. AE: Stomatitis, Diarrhea... AEs leading to discontinuation/dose reduction: Stomatitis (1.4%) Sources: Page: p.1310Diarrhea (1.4%) Eosinophilia (1.4%) Leukopenia (1.4%) |
6 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: Page: p.2 |
healthy, 27+/-5 n = 15 Health Status: healthy Age Group: 27+/-5 Sex: M+F Population Size: 15 Sources: Page: p.2 |
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6 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: Page: p.254 |
unhealthy, 45-63 n = 67 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 45-63 Sex: M+F Population Size: 67 Sources: Page: p.254 |
Disc. AE: Exanthema, Pruritus... AEs leading to discontinuation/dose reduction: Exanthema (7.5%) Sources: Page: p.254Pruritus (6%) Diarrhea (3%) Nausea (1.5%) Bowel obstruction (1.5%) Glomerulonephritis (1.5%) Nephropathies (1.5%) Polyneuropathy (1.5%) Sweating (1.5%) Dry mouth (1.5%) |
27 mg 1 times / day multiple, oral (total daily dose) Overdose Dose: 27 mg, 1 times / day Route: oral Route: multiple Dose: 27 mg, 1 times / day Sources: |
unhealthy, 50 n = 1 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 50 Sex: F Population Size: 1 Sources: |
Disc. AE: Encephalopathy, Peripheral neuropathy... AEs leading to discontinuation/dose reduction: Encephalopathy Sources: Peripheral neuropathy |
3 mg 2 times / day multiple, oral Recommended Dose: 3 mg, 2 times / day Route: oral Route: multiple Dose: 3 mg, 2 times / day Sources: Page: p.266 |
unhealthy, 51 n = 115 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 51 Sex: M+F Population Size: 115 Sources: Page: p.266 |
Disc. AE: Distress gastrointestinal, Diarrhea... AEs leading to discontinuation/dose reduction: Distress gastrointestinal (0.9%) Sources: Page: p.266Diarrhea (3.5%) Rash (3.5%) Mucosal ulceration (2.6%) Leukopenia (0.9%) Proteinuria (2.6%) |
3 mg 3 times / day multiple, oral Recommended Dose: 3 mg, 3 times / day Route: oral Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Rheumatoid arthritis Sources: |
Disc. AE: Hemoglobin decreased, Leukopenia... AEs leading to discontinuation/dose reduction: Hemoglobin decreased Sources: Leukopenia Agranulocytosis Thrombocytopenia Proteinuria Hematuria Pruritus Rash Stomatitis Diarrhea |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Diarrhea | 1.4% Disc. AE |
3 mg 2 times / day multiple, oral Recommended Dose: 3 mg, 2 times / day Route: oral Route: multiple Dose: 3 mg, 2 times / day Sources: Page: p.1310 |
unhealthy, 22-76 n = 72 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 22-76 Sex: M+F Population Size: 72 Sources: Page: p.1310 |
Eosinophilia | 1.4% Disc. AE |
3 mg 2 times / day multiple, oral Recommended Dose: 3 mg, 2 times / day Route: oral Route: multiple Dose: 3 mg, 2 times / day Sources: Page: p.1310 |
unhealthy, 22-76 n = 72 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 22-76 Sex: M+F Population Size: 72 Sources: Page: p.1310 |
Leukopenia | 1.4% Disc. AE |
3 mg 2 times / day multiple, oral Recommended Dose: 3 mg, 2 times / day Route: oral Route: multiple Dose: 3 mg, 2 times / day Sources: Page: p.1310 |
unhealthy, 22-76 n = 72 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 22-76 Sex: M+F Population Size: 72 Sources: Page: p.1310 |
Stomatitis | 1.4% Disc. AE |
3 mg 2 times / day multiple, oral Recommended Dose: 3 mg, 2 times / day Route: oral Route: multiple Dose: 3 mg, 2 times / day Sources: Page: p.1310 |
unhealthy, 22-76 n = 72 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 22-76 Sex: M+F Population Size: 72 Sources: Page: p.1310 |
Bowel obstruction | 1.5% Disc. AE |
6 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: Page: p.254 |
unhealthy, 45-63 n = 67 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 45-63 Sex: M+F Population Size: 67 Sources: Page: p.254 |
Dry mouth | 1.5% Disc. AE |
6 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: Page: p.254 |
unhealthy, 45-63 n = 67 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 45-63 Sex: M+F Population Size: 67 Sources: Page: p.254 |
Glomerulonephritis | 1.5% Disc. AE |
6 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: Page: p.254 |
unhealthy, 45-63 n = 67 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 45-63 Sex: M+F Population Size: 67 Sources: Page: p.254 |
Nausea | 1.5% Disc. AE |
6 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: Page: p.254 |
unhealthy, 45-63 n = 67 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 45-63 Sex: M+F Population Size: 67 Sources: Page: p.254 |
Nephropathies | 1.5% Disc. AE |
6 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: Page: p.254 |
unhealthy, 45-63 n = 67 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 45-63 Sex: M+F Population Size: 67 Sources: Page: p.254 |
Polyneuropathy | 1.5% Disc. AE |
6 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: Page: p.254 |
unhealthy, 45-63 n = 67 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 45-63 Sex: M+F Population Size: 67 Sources: Page: p.254 |
Sweating | 1.5% Disc. AE |
6 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: Page: p.254 |
unhealthy, 45-63 n = 67 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 45-63 Sex: M+F Population Size: 67 Sources: Page: p.254 |
Diarrhea | 3% Disc. AE |
6 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: Page: p.254 |
unhealthy, 45-63 n = 67 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 45-63 Sex: M+F Population Size: 67 Sources: Page: p.254 |
Pruritus | 6% Disc. AE |
6 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: Page: p.254 |
unhealthy, 45-63 n = 67 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 45-63 Sex: M+F Population Size: 67 Sources: Page: p.254 |
Exanthema | 7.5% Disc. AE |
6 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: Page: p.254 |
unhealthy, 45-63 n = 67 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 45-63 Sex: M+F Population Size: 67 Sources: Page: p.254 |
Encephalopathy | Disc. AE | 27 mg 1 times / day multiple, oral (total daily dose) Overdose Dose: 27 mg, 1 times / day Route: oral Route: multiple Dose: 27 mg, 1 times / day Sources: |
unhealthy, 50 n = 1 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 50 Sex: F Population Size: 1 Sources: |
Peripheral neuropathy | Disc. AE | 27 mg 1 times / day multiple, oral (total daily dose) Overdose Dose: 27 mg, 1 times / day Route: oral Route: multiple Dose: 27 mg, 1 times / day Sources: |
unhealthy, 50 n = 1 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 50 Sex: F Population Size: 1 Sources: |
Distress gastrointestinal | 0.9% Disc. AE |
3 mg 2 times / day multiple, oral Recommended Dose: 3 mg, 2 times / day Route: oral Route: multiple Dose: 3 mg, 2 times / day Sources: Page: p.266 |
unhealthy, 51 n = 115 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 51 Sex: M+F Population Size: 115 Sources: Page: p.266 |
Leukopenia | 0.9% Disc. AE |
3 mg 2 times / day multiple, oral Recommended Dose: 3 mg, 2 times / day Route: oral Route: multiple Dose: 3 mg, 2 times / day Sources: Page: p.266 |
unhealthy, 51 n = 115 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 51 Sex: M+F Population Size: 115 Sources: Page: p.266 |
Mucosal ulceration | 2.6% Disc. AE |
3 mg 2 times / day multiple, oral Recommended Dose: 3 mg, 2 times / day Route: oral Route: multiple Dose: 3 mg, 2 times / day Sources: Page: p.266 |
unhealthy, 51 n = 115 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 51 Sex: M+F Population Size: 115 Sources: Page: p.266 |
Proteinuria | 2.6% Disc. AE |
3 mg 2 times / day multiple, oral Recommended Dose: 3 mg, 2 times / day Route: oral Route: multiple Dose: 3 mg, 2 times / day Sources: Page: p.266 |
unhealthy, 51 n = 115 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 51 Sex: M+F Population Size: 115 Sources: Page: p.266 |
Diarrhea | 3.5% Disc. AE |
3 mg 2 times / day multiple, oral Recommended Dose: 3 mg, 2 times / day Route: oral Route: multiple Dose: 3 mg, 2 times / day Sources: Page: p.266 |
unhealthy, 51 n = 115 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 51 Sex: M+F Population Size: 115 Sources: Page: p.266 |
Rash | 3.5% Disc. AE |
3 mg 2 times / day multiple, oral Recommended Dose: 3 mg, 2 times / day Route: oral Route: multiple Dose: 3 mg, 2 times / day Sources: Page: p.266 |
unhealthy, 51 n = 115 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 51 Sex: M+F Population Size: 115 Sources: Page: p.266 |
Agranulocytosis | Disc. AE | 3 mg 3 times / day multiple, oral Recommended Dose: 3 mg, 3 times / day Route: oral Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Rheumatoid arthritis Sources: |
Diarrhea | Disc. AE | 3 mg 3 times / day multiple, oral Recommended Dose: 3 mg, 3 times / day Route: oral Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Rheumatoid arthritis Sources: |
Hematuria | Disc. AE | 3 mg 3 times / day multiple, oral Recommended Dose: 3 mg, 3 times / day Route: oral Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Rheumatoid arthritis Sources: |
Hemoglobin decreased | Disc. AE | 3 mg 3 times / day multiple, oral Recommended Dose: 3 mg, 3 times / day Route: oral Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Rheumatoid arthritis Sources: |
Leukopenia | Disc. AE | 3 mg 3 times / day multiple, oral Recommended Dose: 3 mg, 3 times / day Route: oral Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Rheumatoid arthritis Sources: |
Proteinuria | Disc. AE | 3 mg 3 times / day multiple, oral Recommended Dose: 3 mg, 3 times / day Route: oral Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Rheumatoid arthritis Sources: |
Pruritus | Disc. AE | 3 mg 3 times / day multiple, oral Recommended Dose: 3 mg, 3 times / day Route: oral Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Rheumatoid arthritis Sources: |
Rash | Disc. AE | 3 mg 3 times / day multiple, oral Recommended Dose: 3 mg, 3 times / day Route: oral Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Rheumatoid arthritis Sources: |
Stomatitis | Disc. AE | 3 mg 3 times / day multiple, oral Recommended Dose: 3 mg, 3 times / day Route: oral Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Rheumatoid arthritis Sources: |
Thrombocytopenia | Disc. AE | 3 mg 3 times / day multiple, oral Recommended Dose: 3 mg, 3 times / day Route: oral Route: multiple Dose: 3 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Rheumatoid arthritis Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Proteinuria in gold-treated rheumatoid arthritis. | 1984 Aug |
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An analysis of worldwide safety experience with auranofin. | 1985 Aug |
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Hematuria in patients with rheumatoid arthritis receiving gold and D-penicillamine. | 1987 Feb |
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[Gold-induced severe cholestatic jaundice in rheumatoid arthritis patient and effect of repeated steroid pulse therapy]. | 1992 Oct |
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Auranofin inhibits interleukin-1beta-induced transcript of cyclooxygenase-2 on cultured human synoviocytes. | 1999 Nov 26 |
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Thiol-reactive metal compounds inhibit NF-kappa B activation by blocking I kappa B kinase. | 2000 Jun 1 |
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Nitritoid reactions: case reports, review, and recommendations for management. | 2001 Oct |
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Auranofin induces apoptosis and when combined with retinoic acid enhances differentiation of acute promyelocytic leukaemia cells in vitro. | 2004 Jun |
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Gold complexes inhibit mitochondrial thioredoxin reductase: consequences on mitochondrial functions. | 2004 Oct |
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Sublethal concentrations of diverse gold compounds inhibit mammalian cytosolic thioredoxin reductase (TrxR1). | 2006 Sep |
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Treatment of lung cancer cells with cytotoxic levels of sodium selenite: effects on the thioredoxin system. | 2008 Jun 1 |
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The selenium-independent inherent pro-oxidant NADPH oxidase activity of mammalian thioredoxin reductase and its selenium-dependent direct peroxidase activities. | 2010 Jul 9 |
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Metal-based inhibition of poly(ADP-ribose) polymerase--the guardian angel of DNA. | 2011 Apr 14 |
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Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
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Substrate and inhibitor specificities differ between human cytosolic and mitochondrial thioredoxin reductases: Implications for development of specific inhibitors. | 2011 Mar 15 |
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Mitochondrial protection by the thioredoxin-2 and glutathione systems in an in vitro endothelial model of sepsis. | 2011 May 15 |
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Auranofin protects against cocaine-induced hepatic injury through induction of heme oxygenase-1. | 2011 Oct |
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Enhancement of carboplatin-mediated lung cancer cell killing by simultaneous disruption of glutathione and thioredoxin metabolism. | 2011 Oct 1 |
Patents
Sample Use Guides
The usual adult dosage is 6 mg daily, given either as 3 mg twice daily or 6 mg once daily. Initiation of therapy at dosages exceeding 6 mg daily is not recommended because it is associated with an increased incidence of diarrhea. If response is inadequate after six months, an increase to 9 mg (3 mg three times daily) may be tolerated.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26895605
Auranofin possesses potent antibacterial activity against all tested strains of S. aureus, including meticillin-resistant S. aureus (MRSA), vancomycin-intermediate S. aureus (VISA) and vancomycin-resistant S. aureus (VRSA), with minimum inhibitory concentrations (MICs) ranging from 0.0625μg/mL to 0.125μg/mL.
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WHO-ATC |
M01CB03
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WHO-VATC |
QM01CB03
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FDA ORPHAN DRUG |
305210
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NCI_THESAURUS |
C574
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LIVERTOX |
76
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DTXSID4020115
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251-801-9
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CHEMBL1366
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SUB05610MIG
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6918453
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321521
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6306
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3H04W2810V
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34031-32-8
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C65242
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D001310
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3H04W2810V
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100000086659
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1227
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DB00995
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4122
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m2139
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Auranofin
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7172
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AURANOFIN
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ACTIVE MOIETY