Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C23H20N2O3S |
| Molecular Weight | 404.482 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[O-][S+](CCC1C(=O)N(N(C1=O)C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChIKey=MBGGBVCUIVRRBF-UHFFFAOYSA-N
InChI=1S/C23H20N2O3S/c26-22-21(16-17-29(28)20-14-8-3-9-15-20)23(27)25(19-12-6-2-7-13-19)24(22)18-10-4-1-5-11-18/h1-15,21H,16-17H2
| Molecular Formula | C23H20N2O3S |
| Molecular Weight | 404.482 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB01138Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/anturane.html
Sources: http://www.drugbank.ca/drugs/DB01138
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/anturane.html
Sulfinpyrazone was approved by the U.S. Food and Drug Administration (FDA) on May 13, 1959. It was developed and marketed as Anturane® by Novartis. Sulfinpyrazone is an oral uricosuric agent (pyrazolone derivative) used to treat chronic or intermittent gouty arthritis. Sulfinpyrazone competitively inhibits the reabsorption of uric acid at the proximal convoluted tubule, thereby facilitating urinary excretion of uric acid and decreasing plasma urate concentrations. This is likely done through inhibition of the urate anion transporter (hURAT1) as well as the human organic anion transporter 4 (hOAT4). Sulfinpyrazone is not intended for the treatment of acute attacks because it lacks therapeutically useful analgesic and anti-inflammatory effects. Sulfinpyrazone and its sulfide metabolite possess COX inhibitory effects. Sulfinpyrazone has also been shown to be a UDP-glucuronsyltransferase inhibitor and a very potent CYP2C9 inhibitor. Sulfinpyrazone is also known to be a cystic fibrosis transmembrane conductance regulator (CFTR) inhibitor as well as an inhibitor of several multridrug resistance proteins (MRPs). Branded and generic forms of sulfinpyrazone have been discontinued in the US.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL5748 Sources: http://www.drugbank.ca/drugs/DB01138 |
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Target ID: CHEMBL3004 Sources: http://www.drugbank.ca/drugs/DB01138 |
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Target ID: CHEMBL2046258 |
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Target ID: CHEMBL6120 |
100.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Anturane Approved UseAnturane is indicated for the treatment of:
Chronic gouty arthritis
Intermittent gouty arthritis Launch Date1959 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
26 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
13.4 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.2 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
116 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
53 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
13.4 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
9.2 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
79.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059415/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
191.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059415/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059415/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
16.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059415/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
9.96 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.79 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059415/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4.17 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059415/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
3.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059415/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1000 mg single, oral Overdose |
healthy, 24 |
Other AEs: Acute renal failure... |
1000 mg multiple, oral Recommended Dose: 1000 mg Route: oral Route: multiple Dose: 1000 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Acute renal failure... Other AEs: Acute renal failure (low incidence) Sources: |
400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Skin rash... AEs leading to discontinuation/dose reduction: Skin rash (rare) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Acute renal failure | 1000 mg single, oral Overdose |
healthy, 24 |
|
| Acute renal failure | low incidence | 1000 mg multiple, oral Recommended Dose: 1000 mg Route: oral Route: multiple Dose: 1000 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
| Skin rash | rare Disc. AE |
400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| weak | ||||
Page: 6.0 |
yes [IC50 103 uM] | |||
Page: 6.0 |
yes [IC50 11 uM] | |||
Page: 6.0 |
yes [IC50 158 uM] | |||
Page: 6.0 |
yes [IC50 16 uM] | |||
Page: 6.0 |
yes [IC50 187 uM] | |||
Page: 6.0 |
yes [IC50 267 uM] | |||
Page: 6.0 |
yes [IC50 2741 uM] | |||
Page: 6.0 |
yes [IC50 402 uM] | |||
Page: 9.0 |
yes [IC50 420 uM] | |||
Page: 6.0 |
yes [IC50 46 uM] | |||
Page: 6.0 |
yes [IC50 58 uM] | |||
Page: 6.0 |
yes [IC50 651 uM] | |||
| yes [Ki 230 uM] | ||||
Page: 77.0 |
yes | |||
Page: 1.0 |
yes | |||
Page: 184.0 |
yes | |||
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). | 2013-12 |
|
| Interactions of urate transporter URAT1 in human kidney with uricosuric drugs. | 2011-02 |
|
| HepaRG cells as an in vitro model for evaluation of cytochrome P450 induction in humans. | 2008-01 |
|
| Morin (3,5,7,2',4'-pentahydroxyflavone) exhibits potent inhibitory actions on urate transport by the human urate anion transporter (hURAT1) expressed in human embryonic kidney cells. | 2007-06 |
|
| In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007-01 |
|
| Use of immortalized human hepatocytes to predict the magnitude of clinical drug-drug interactions caused by CYP3A4 induction. | 2006-10 |
|
| Prediction of CYP2C9-mediated drug-drug interactions: a comparison using data from recombinant enzymes and human hepatocytes. | 2005-11 |
|
| Combined effects of GSTP1 and MRP1 in melanoma drug resistance. | 2005-07-25 |
|
| High-throughput screening with HyperCyt flow cytometry to detect small molecule formylpeptide receptor ligands. | 2005-06 |
|
| Glutathione S-transferase M1 and multidrug resistance protein 1 act in synergy to protect melanoma cells from vincristine effects. | 2004-04 |
|
| Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers. | 2004-03 |
|
| Role of multidrug resistance protein 2 (MRP2, ABCC2) in alkylating agent detoxification: MRP2 potentiates glutathione S-transferase A1-1-mediated resistance to chlorambucil cytotoxicity. | 2004-01 |
|
| Functional expression of the multidrug resistance protein 1 in microglia. | 2003-10 |
|
| Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes. | 2003-01-01 |
|
| CYP3A4 induction by drugs: correlation between a pregnane X receptor reporter gene assay and CYP3A4 expression in human hepatocytes. | 2002-07 |
|
| Comparison of furosemide and vinblastine secretion from cell lines overexpressing multidrug resistance protein (P-glycoprotein) and multidrug resistance-associated proteins (MRP1 and MRP2). | 2002 |
|
| A reporter gene assay to assess the molecular mechanisms of xenobiotic-dependent induction of the human CYP3A4 gene in vitro. | 1999-03 |
|
| Acute renal failure due to sulfinpyrazone. | 1998-05 |
|
| Development of an in vitro reporter gene assay to assess xenobiotic induction of the human CYP3A4 gene. | 1998-03-26 |
|
| Interaction of sulfonamide and sulfone compounds with Toxoplasma gondii dihydropteroate synthase. | 1990-02 |
|
| [Acute tubulo-interstitial nephropathy associated with ingestion of sulfinpyrazone]. | 1985-02-23 |
|
| Sulfinpyrazone: risk for renal insufficiency. | 1984-03 |
|
| Acute renal failure secondary to sulfinpyrazone treatment after myocardial infarction. | 1984 |
|
| [Acute interstitial nephritis and kidney failure requiring dialysis after sulfinpyrazone therapy]. | 1984 |
|
| Transcoronary platelet thromboxane A2 formation without platelet trapping in patients with coronary stenosis-effect of sulphinpyrazone treatment. | 1983-12-30 |
|
| Sulfinpyrazone-associated acute renal failure. | 1983-07 |
|
| Decrease in renal function due to sulphinpyrazone treatment early after myocardial infarction. | 1983-03 |
|
| Oliguric acute renal failure after treatment with sulfinpyrazone. | 1983-01 |
|
| [Sulfinpyrazone-associated renal failure (author's transl)]. | 1982-07-09 |
|
| Non oliguric acute renal failure after treatment with sulfinpyrazone. | 1982-05 |
|
| Acute renal failure following sulfinpyrazone therapy. | 1982-04 |
|
| Sulphinpyrazone--induced decrease in renal function: a review of reports with discussion of pathogenesis. | 1982 |
|
| Renal dysfunction due to anturane. | 1981-11-05 |
|
| Acute renal dysfunction due to sulfinpyrazone therapy in post-myocardial infarction cardiomegaly: reversible hypersensitive interstitial nephritis. | 1981-08 |
|
| Renal dysfunction due to anturane. | 1981-07-09 |
|
| Sulfinpyrazone induced uric acid urolithiasis with acute renal failure. | 1981-07 |
|
| Effects of sulfinpyrazone, aspirin and propranolol on the isoproterenol-induced myocardial necrosis. | 1981-07 |
|
| Sulphinpyrazone-induced acute renal failure. | 1981-02-21 |
|
| [Acute renal failure induced by sulfinpyrazone (author's transl)]. | 1981 |
|
| Are agents affecting platelet functions clinically useful? | 1976-12 |
|
| Abnormalities of urinary sediment and renal failure following sulfinpyrazone therapy. | 1976-09 |
|
| Acute myelomonocytic leukaemia and multiple myeloma after sulphinpyrazone and colchicine treatment of gout. | 1976-07-10 |
Patents
Sample Use Guides
Initial
200-400 mg daily in two divided doses, with meals or milk, gradually increasing when necessary to full maintenance dosage in one week.
Maintenance
400 mg daily, given in two divided doses, as above. This dosage may be increased to 800 mg daily, if necessary, and may sometimes be reduced to as low as 200 mg daily after the blood urate level has been controlled.
Route of Administration:
Oral
| Substance Class |
Chemical
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V6OFU47K3W
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NCI_THESAURUS |
C921
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M04AB02
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LIVERTOX |
913
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QM04AB02
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DB01138
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D013442
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m10349
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SULFINPYRAZONE
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TARGET -> INHIBITOR | |||
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METABOLIC ENZYME -> INDUCER | |||
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TRANSPORTER -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> INDUCER | |||
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TARGET -> INHIBITOR |
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Biological Half-life | PHARMACOKINETIC |
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