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
| Molecular Formula | C20H35AuO9PS |
| Molecular Weight | 679.492 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|||
Target ID: P30044|||Q9UJU4 Gene ID: 25824.0 Gene Symbol: PRDX5 Target Organism: Homo sapiens (Human) |
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 Date1985 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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: |
unhealthy, 22-76 |
Disc. AE: Stomatitis, Diarrhea... AEs leading to discontinuation/dose reduction: Stomatitis (1.4%) Sources: Diarrhea (1.4%) Eosinophilia (1.4%) Leukopenia (1.4%) |
6 mg 1 times / day multiple, oral Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
healthy, 27+/-5 |
|
6 mg 1 times / day multiple, oral Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 45-63 |
Disc. AE: Exanthema, Pruritus... AEs leading to discontinuation/dose reduction: Exanthema (7.5%) Sources: Pruritus (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 Overdose Dose: 27 mg, 1 times / day Route: oral Route: multiple Dose: 27 mg, 1 times / day Sources: |
unhealthy, 50 Health Status: unhealthy Age Group: 50 Sex: F 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: |
unhealthy, 51 |
Disc. AE: Distress gastrointestinal, Diarrhea... AEs leading to discontinuation/dose reduction: Distress gastrointestinal (0.9%) Sources: Diarrhea (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 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: |
unhealthy, 22-76 |
| 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: |
unhealthy, 22-76 |
| 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: |
unhealthy, 22-76 |
| 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: |
unhealthy, 22-76 |
| Bowel obstruction | 1.5% Disc. AE |
6 mg 1 times / day multiple, oral Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 45-63 |
| Dry mouth | 1.5% Disc. AE |
6 mg 1 times / day multiple, oral Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 45-63 |
| Glomerulonephritis | 1.5% Disc. AE |
6 mg 1 times / day multiple, oral Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 45-63 |
| Nausea | 1.5% Disc. AE |
6 mg 1 times / day multiple, oral Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 45-63 |
| Nephropathies | 1.5% Disc. AE |
6 mg 1 times / day multiple, oral Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 45-63 |
| Polyneuropathy | 1.5% Disc. AE |
6 mg 1 times / day multiple, oral Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 45-63 |
| Sweating | 1.5% Disc. AE |
6 mg 1 times / day multiple, oral Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 45-63 |
| Diarrhea | 3% Disc. AE |
6 mg 1 times / day multiple, oral Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 45-63 |
| Pruritus | 6% Disc. AE |
6 mg 1 times / day multiple, oral Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 45-63 |
| Exanthema | 7.5% Disc. AE |
6 mg 1 times / day multiple, oral Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 45-63 |
| Encephalopathy | Disc. AE | 27 mg 1 times / day multiple, oral Overdose Dose: 27 mg, 1 times / day Route: oral Route: multiple Dose: 27 mg, 1 times / day Sources: |
unhealthy, 50 Health Status: unhealthy Age Group: 50 Sex: F Sources: |
| Peripheral neuropathy | Disc. AE | 27 mg 1 times / day multiple, oral Overdose Dose: 27 mg, 1 times / day Route: oral Route: multiple Dose: 27 mg, 1 times / day Sources: |
unhealthy, 50 Health Status: unhealthy Age Group: 50 Sex: F 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: |
unhealthy, 51 |
| 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: |
unhealthy, 51 |
| 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: |
unhealthy, 51 |
| 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: |
unhealthy, 51 |
| 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: |
unhealthy, 51 |
| 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: |
unhealthy, 51 |
| 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 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 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 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 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 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 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 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 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 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 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells. | 2013-10 |
|
| Enhancement of carboplatin-mediated lung cancer cell killing by simultaneous disruption of glutathione and thioredoxin metabolism. | 2011-10-01 |
|
| Auranofin protects against cocaine-induced hepatic injury through induction of heme oxygenase-1. | 2011-10 |
|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011-07-14 |
|
| Inhibition of thioredoxin reductase by auranofin induces apoptosis in adriamycin-resistant human K562 chronic myeloid leukemia cells. | 2011-06 |
|
| Mitochondrial protection by the thioredoxin-2 and glutathione systems in an in vitro endothelial model of sepsis. | 2011-05-15 |
|
| Metal-based inhibition of poly(ADP-ribose) polymerase--the guardian angel of DNA. | 2011-04-14 |
|
| Substrate and inhibitor specificities differ between human cytosolic and mitochondrial thioredoxin reductases: Implications for development of specific inhibitors. | 2011-03-15 |
|
| The gold compound auranofin induces apoptosis of human multiple myeloma cells through both down-regulation of STAT3 and inhibition of NF-κB activity. | 2011-02 |
|
| The selenium-independent inherent pro-oxidant NADPH oxidase activity of mammalian thioredoxin reductase and its selenium-dependent direct peroxidase activities. | 2010-07-09 |
|
| Treatment of human cancer cells with selenite or tellurite in combination with auranofin enhances cell death due to redox shift. | 2009-09-15 |
|
| The thioredoxin reductase inhibitor auranofin triggers apoptosis through a Bax/Bak-dependent process that involves peroxiredoxin 3 oxidation. | 2008-10-30 |
|
| Treatment of lung cancer cells with cytotoxic levels of sodium selenite: effects on the thioredoxin system. | 2008-06-01 |
|
| Ifosfamide induces acute renal failure via inhibition of the thioredoxin reductase activity. | 2007-12-15 |
|
| Auranofin, as an anti-rheumatic gold compound, suppresses LPS-induced homodimerization of TLR4. | 2006-12-01 |
|
| Sublethal concentrations of diverse gold compounds inhibit mammalian cytosolic thioredoxin reductase (TrxR1). | 2006-09 |
|
| A mass spectrometric investigation of the binding of gold antiarthritic agents and the metabolite [Au(CN)2]- to human serum albumin. | 2006-07 |
|
| Gold complexes inhibit mitochondrial thioredoxin reductase: consequences on mitochondrial functions. | 2004-10 |
|
| Auranofin increases apoptosis and ischaemia-reperfusion injury in the rat isolated heart. | 2004-06-12 |
|
| Auranofin induces apoptosis and when combined with retinoic acid enhances differentiation of acute promyelocytic leukaemia cells in vitro. | 2004-06 |
|
| Nitritoid reactions: case reports, review, and recommendations for management. | 2001-10 |
|
| HLA-DRB1*0301 and DQA1*0501 in RA. | 2001-07 |
|
| Thiol-reactive metal compounds inhibit NF-kappa B activation by blocking I kappa B kinase. | 2000-06-01 |
|
| Auranofin inhibits interleukin-1beta-induced transcript of cyclooxygenase-2 on cultured human synoviocytes. | 1999-11-26 |
|
| [Gold-induced severe cholestatic jaundice in rheumatoid arthritis patient and effect of repeated steroid pulse therapy]. | 1992-10 |
|
| Hematuria in patients with rheumatoid arthritis receiving gold and D-penicillamine. | 1987-02 |
|
| Nephrotic syndrome after oral gold. | 1986-08 |
|
| Long-term efficacy and safety of auranofin: a review of clinical experience. | 1986 |
|
| Auranofin versus penicillamine in rheumatoid arthritis. One-year results from a prospective clinical investigation. | 1986 |
|
| An analysis of worldwide safety experience with auranofin. | 1985-08 |
|
| Neurotoxicity following a very high dose of oral gold (auranofin) | 1984-11 |
|
| Proteinuria in gold-treated rheumatoid arthritis. | 1984-08 |
|
| Gold nephropathy due to auranofin obscured by tolmetin pseudoproteinuria. | 1984-06 |
|
| [Multicenter double-blind comparison of auranofin and Tauredon]. | 1984 |
|
| The subacute and chronic toxicity of SK&F 36914 and SK&F D-39162 in dogs. | 1978-08 |
|
| The subacute and chronic toxicity of SK&F 36914, SK&F D-39162 and gold sodium thiomalate in rats. | 1978-08 |
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
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.
| Substance Class |
Chemical
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3H04W2810V
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WHO-ATC |
M01CB03
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QM01CB03
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FDA ORPHAN DRUG |
305210
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NCI_THESAURUS |
C574
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76
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Auranofin
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AURANOFIN
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