Identification

Name
Sulfinpyrazone
Accession Number
DB01138  (APRD00620)
Type
Small Molecule
Groups
Approved
Description

A uricosuric drug that is used to reduce the serum urate levels in gout therapy. It lacks anti-inflammatory, analgesic, and diuretic properties.

Structure
Thumb
Synonyms
  • 1,2-Diphenyl-3,5-dioxo-4-(2-phenylsulfinylethyl)pyrazolidine
  • 1,2-Diphenyl-4-(2'-phenylsulfinethyl)-3,5-pyrazolidinedione
  • 4-(2-Benzenesulfinylethyl)-1,2-diphenylpyrazolidine-3,5-dione
  • Sulfoxyphenylpyrazolidine
External IDs
NSC-75925 / USAF GE-13
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Antazone Tab 100mgTablet100 mgOralIcn Pharmaceuticals1980-12-312005-04-26Canada
Antazone Tab 200mgTablet200 mgOralIcn Pharmaceuticals1980-12-312005-04-26Canada
Anturan 100mgTablet100 mgOralNovartis1959-12-311999-08-04Canada
Anturan 200mgTablet200 mgOralNovartis1961-12-311999-08-04Canada
Novo-pyrazone Tab 100mgTablet100 mgOralNovopharm Limited1979-12-312005-08-10Canada
Novo-pyrazone Tab 200mgTablet200 mgOralNovopharm Limited1979-12-312005-08-10Canada
Nu-sulfinpyrazone Tab 100mgTablet100 mgOralNu Pharm Inc1993-12-312008-02-20Canada
Nu-sulfinpyrazone Tab 200mgTablet200 mgOralNu Pharm Inc1993-12-312012-09-04Canada
SulfinpyrazoneTablet200 mgOralAa Pharma Inc1978-12-31Not applicableCanada
Sulfinpyrazone 100 TabTablet100 mgOralPro Doc Limitee1979-12-312003-07-31Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Sulfinpyrazone Tab 100mgTablet100 mgOralApotex Corporation1978-12-312008-02-19Canada
International/Other Brands
Anturane
Categories
UNII
V6OFU47K3W
CAS number
57-96-5
Weight
Average: 404.482
Monoisotopic: 404.119463206
Chemical Formula
C23H20N2O3S
InChI Key
MBGGBVCUIVRRBF-UHFFFAOYSA-N
InChI
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
IUPAC Name
4-[2-(benzenesulfinyl)ethyl]-1,2-diphenylpyrazolidine-3,5-dione
SMILES
O=C1C(CCS(=O)C2=CC=CC=C2)C(=O)N(N1C1=CC=CC=C1)C1=CC=CC=C1

Pharmacology

Indication

For the treatment of gout and gouty arthritis.

Structured Indications
Pharmacodynamics

Sulfinpyrazone's pharmacologic activity is the potentiation of the urinary excretion of uric acid. It is useful for reducing the blood urate levels in patients with chronic tophaceous gout and acute intermittent gout, and for promoting the resorption of tophi.

Mechanism of action

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).

TargetActionsOrganism
AMultidrug resistance-associated protein 1
inhibitor
Human
ACanalicular multispecific organic anion transporter 1
inhibitor
Human
ASolute carrier family 22 member 12
inhibitor
Human
UNuclear receptor subfamily 1 group I member 2
activator
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding

98-99%

Metabolism
Route of elimination
Not Available
Half life

Approximately 4-6 hours

Clearance
Not Available
Toxicity

Symptoms of overdose include nausea, vomiting, diarrhea, epigastric pain, ataxia, labored respiration, convulsions, coma. Possible symptoms, seen after overdosage with other pyrazolone derivatives: anemia, jaundice, and ulceration.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Sulfinpyrazone can be increased when it is combined with Abiraterone.Approved
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Sulfinpyrazone.Approved
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Sulfinpyrazone.Approved
AmiodaroneThe metabolism of Sulfinpyrazone can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Sulfinpyrazone can be increased when it is combined with Aprepitant.Approved, Investigational
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Sulfinpyrazone.Approved, Investigational
AtazanavirThe metabolism of Sulfinpyrazone can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Sulfinpyrazone can be decreased when combined with Atomoxetine.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Sulfinpyrazone is combined with Atorvastatin.Approved
BoceprevirThe metabolism of Sulfinpyrazone can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Sulfinpyrazone can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Sulfinpyrazone can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Sulfinpyrazone.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Sulfinpyrazone.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Sulfinpyrazone.Approved, Investigational
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Sulfinpyrazone.Approved
CapecitabineThe metabolism of Sulfinpyrazone can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Sulfinpyrazone can be increased when combined with Carbamazepine.Approved, Investigational
CelecoxibThe metabolism of Sulfinpyrazone can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Sulfinpyrazone can be increased when it is combined with Ceritinib.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Sulfinpyrazone.Withdrawn
CholecalciferolThe metabolism of Sulfinpyrazone can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
ClarithromycinThe metabolism of Sulfinpyrazone can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Sulfinpyrazone can be decreased when combined with Clemastine.Approved
ClorindioneThe metabolism of Clorindione can be decreased when combined with Sulfinpyrazone.Experimental
ClotrimazoleThe metabolism of Sulfinpyrazone can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Sulfinpyrazone can be decreased when combined with Cobicistat.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Sulfinpyrazone.Approved
ConivaptanThe serum concentration of Sulfinpyrazone can be increased when it is combined with Conivaptan.Approved, Investigational
CrisaboroleThe metabolism of Sulfinpyrazone can be decreased when combined with Crisaborole.Approved
CrizotinibThe metabolism of Sulfinpyrazone can be decreased when combined with Crizotinib.Approved
CyclosporineThe serum concentration of Cyclosporine can be decreased when it is combined with Sulfinpyrazone.Approved, Investigational, Vet Approved
Dabigatran etexilateSulfinpyrazone may increase the anticoagulant activities of Dabigatran etexilate.Approved
DabrafenibThe serum concentration of Sulfinpyrazone can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Sulfinpyrazone can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Sulfinpyrazone can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Sulfinpyrazone can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Sulfinpyrazone can be decreased when combined with Delavirdine.Approved
DicoumarolThe metabolism of Dicoumarol can be decreased when combined with Sulfinpyrazone.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Sulfinpyrazone.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Sulfinpyrazone.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Sulfinpyrazone.Experimental
DihydroergotamineThe metabolism of Sulfinpyrazone can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Sulfinpyrazone can be decreased when combined with Diltiazem.Approved
DiphenadioneThe metabolism of Diphenadione can be decreased when combined with Sulfinpyrazone.Experimental
DosulepinThe metabolism of Sulfinpyrazone can be decreased when combined with Dosulepin.Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Sulfinpyrazone.Approved, Investigational
DoxycyclineThe metabolism of Sulfinpyrazone can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Sulfinpyrazone can be decreased when combined with Dronedarone.Approved
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Sulfinpyrazone.Approved
EfavirenzThe metabolism of Sulfinpyrazone can be decreased when combined with Efavirenz.Approved, Investigational
EnzalutamideThe serum concentration of Sulfinpyrazone can be decreased when it is combined with Enzalutamide.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Sulfinpyrazone.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Sulfinpyrazone.Approved
ErythromycinThe metabolism of Sulfinpyrazone can be decreased when combined with Erythromycin.Approved, Vet Approved
Ethyl biscoumacetateThe metabolism of Ethyl biscoumacetate can be decreased when combined with Sulfinpyrazone.Withdrawn
EtravirineThe metabolism of Sulfinpyrazone can be decreased when combined with Etravirine.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Sulfinpyrazone.Approved
FelodipineThe metabolism of Sulfinpyrazone can be decreased when combined with Felodipine.Approved, Investigational
FloxuridineThe metabolism of Sulfinpyrazone can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Sulfinpyrazone can be decreased when combined with Fluconazole.Approved
FluindioneThe metabolism of Fluindione can be decreased when combined with Sulfinpyrazone.Investigational
FluorouracilThe metabolism of Sulfinpyrazone can be decreased when combined with Fluorouracil.Approved
FluvastatinThe metabolism of Sulfinpyrazone can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Sulfinpyrazone can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Sulfinpyrazone can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Sulfinpyrazone can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Sulfinpyrazone can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Sulfinpyrazone can be increased when it is combined with Fusidic Acid.Approved
GemfibrozilThe metabolism of Sulfinpyrazone can be decreased when combined with Gemfibrozil.Approved
ImatinibThe metabolism of Sulfinpyrazone can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Sulfinpyrazone can be decreased when combined with Indinavir.Approved
IrbesartanThe metabolism of Sulfinpyrazone can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Sulfinpyrazone can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Sulfinpyrazone can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Sulfinpyrazone can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Sulfinpyrazone can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Sulfinpyrazone can be decreased when combined with Ketoconazole.Approved, Investigational
LapatinibThe metabolism of Sulfinpyrazone can be decreased when combined with Lapatinib.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Sulfinpyrazone.Approved
LeflunomideThe metabolism of Sulfinpyrazone can be decreased when combined with Leflunomide.Approved, Investigational
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Sulfinpyrazone.Approved, Investigational
LobeglitazoneThe metabolism of Sulfinpyrazone can be decreased when combined with Lobeglitazone.Approved, Investigational
LopinavirThe metabolism of Sulfinpyrazone can be decreased when combined with Lopinavir.Approved
LosartanThe metabolism of Sulfinpyrazone can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Sulfinpyrazone can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Sulfinpyrazone can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Sulfinpyrazone can be increased when it is combined with Lumacaftor.Approved
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Sulfinpyrazone.Illicit, Investigational, Withdrawn
ManidipineThe metabolism of Sulfinpyrazone can be decreased when combined with Manidipine.Approved, Investigational
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Sulfinpyrazone.Experimental
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Sulfinpyrazone.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Sulfinpyrazone.Approved
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Sulfinpyrazone.Experimental
MidostaurinThe metabolism of Sulfinpyrazone can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Sulfinpyrazone can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Sulfinpyrazone can be decreased when it is combined with Mitotane.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Sulfinpyrazone.Approved
NefazodoneThe metabolism of Sulfinpyrazone can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Sulfinpyrazone can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Sulfinpyrazone can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Sulfinpyrazone can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Sulfinpyrazone can be decreased when combined with Nicardipine.Approved
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Sulfinpyrazone.Approved, Investigational
NilotinibThe metabolism of Sulfinpyrazone can be decreased when combined with Nilotinib.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Sulfinpyrazone.Approved
OlaparibThe metabolism of Sulfinpyrazone can be decreased when combined with Olaparib.Approved
OmeprazoleThe metabolism of Sulfinpyrazone can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Sulfinpyrazone can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Sulfinpyrazone can be increased when it is combined with Palbociclib.Approved
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Sulfinpyrazone.Approved
PentobarbitalThe metabolism of Sulfinpyrazone can be increased when combined with Pentobarbital.Approved, Vet Approved
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Sulfinpyrazone.Approved, Investigational, Vet Approved, Withdrawn
PhenindioneThe metabolism of Phenindione can be decreased when combined with Sulfinpyrazone.Approved, Investigational
PhenobarbitalThe metabolism of Sulfinpyrazone can be increased when combined with Phenobarbital.Approved
PhenprocoumonThe metabolism of Phenprocoumon can be decreased when combined with Sulfinpyrazone.Approved, Investigational
PhenytoinThe metabolism of Sulfinpyrazone can be increased when combined with Phenytoin.Approved, Vet Approved
PioglitazoneThe metabolism of Sulfinpyrazone can be decreased when combined with Pioglitazone.Approved, Investigational
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Sulfinpyrazone.Approved
PosaconazoleThe metabolism of Sulfinpyrazone can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Sulfinpyrazone.Approved
PrimidoneThe metabolism of Sulfinpyrazone can be increased when combined with Primidone.Approved, Vet Approved
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Sulfinpyrazone.Approved
PyrimethamineThe metabolism of Sulfinpyrazone can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuinineThe metabolism of Sulfinpyrazone can be decreased when combined with Quinine.Approved
RabeprazoleThe metabolism of Sulfinpyrazone can be decreased when combined with Rabeprazole.Approved, Investigational
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Sulfinpyrazone.Approved, Investigational
RifabutinThe metabolism of Sulfinpyrazone can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Sulfinpyrazone can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Sulfinpyrazone can be increased when combined with Rifapentine.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Sulfinpyrazone.Approved, Investigational
RilpivirineThe serum concentration of Rilpivirine can be decreased when it is combined with Sulfinpyrazone.Approved
RosiglitazoneThe metabolism of Sulfinpyrazone can be decreased when combined with Rosiglitazone.Approved, Investigational
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Sulfinpyrazone.Approved
SaquinavirThe metabolism of Sulfinpyrazone can be decreased when combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Sulfinpyrazone.Approved
SecobarbitalThe metabolism of Sulfinpyrazone can be increased when combined with Secobarbital.Approved, Vet Approved
SildenafilThe metabolism of Sulfinpyrazone can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Sulfinpyrazone.Approved
SiltuximabThe serum concentration of Sulfinpyrazone can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Sulfinpyrazone can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Sulfinpyrazone.Approved
SorafenibThe metabolism of Sulfinpyrazone can be decreased when combined with Sorafenib.Approved, Investigational
St. John's WortThe serum concentration of Sulfinpyrazone can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Sulfinpyrazone can be increased when it is combined with Stiripentol.Approved
SulfadiazineThe metabolism of Sulfinpyrazone can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Sulfinpyrazone can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Sulfinpyrazone can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TamoxifenThe metabolism of Sulfinpyrazone can be decreased when combined with Tamoxifen.Approved
TelaprevirThe metabolism of Sulfinpyrazone can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Sulfinpyrazone can be decreased when combined with Telithromycin.Approved
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Sulfinpyrazone.Experimental
TeriflunomideThe metabolism of Sulfinpyrazone can be decreased when combined with Teriflunomide.Approved
TicagrelorThe metabolism of Sulfinpyrazone can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Sulfinpyrazone can be decreased when combined with Ticlopidine.Approved
TioclomarolThe metabolism of Tioclomarol can be decreased when combined with Sulfinpyrazone.Experimental
TocilizumabThe serum concentration of Sulfinpyrazone can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Sulfinpyrazone can be decreased when combined with Tolbutamide.Approved
TopiroxostatThe metabolism of Sulfinpyrazone can be decreased when combined with Topiroxostat.Approved, Investigational
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Sulfinpyrazone.Approved, Investigational
TrimethoprimThe metabolism of Sulfinpyrazone can be decreased when combined with Trimethoprim.Approved, Vet Approved
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Sulfinpyrazone.Approved, Investigational, Nutraceutical
Valproic AcidThe metabolism of Sulfinpyrazone can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Sulfinpyrazone can be decreased when combined with Valsartan.Approved, Investigational
VenlafaxineThe metabolism of Sulfinpyrazone can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Sulfinpyrazone can be decreased when combined with Verapamil.Approved
VincristineThe serum concentration of Vincristine can be increased when it is combined with Sulfinpyrazone.Approved, Investigational
VoriconazoleThe metabolism of Sulfinpyrazone can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinThe metabolism of Warfarin can be decreased when combined with Sulfinpyrazone.Approved
ZafirlukastThe metabolism of Sulfinpyrazone can be decreased when combined with Zafirlukast.Approved, Investigational
ZiprasidoneThe metabolism of Sulfinpyrazone can be decreased when combined with Ziprasidone.Approved
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB15269
KEGG Drug
D00449
KEGG Compound
C07317
PubChem Compound
5342
PubChem Substance
46504918
ChemSpider
5149
ChEBI
9342
ChEMBL
CHEMBL832
Therapeutic Targets Database
DAP000794
PharmGKB
PA451550
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Sulfinpyrazone
ATC Codes
M04AB02 — Sulfinpyrazone
AHFS Codes
  • 40:40.00 — Uricosuric Agents

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
TabletOral100 mg
TabletOral200 mg
Prices
Unit descriptionCostUnit
Apo-Sulfinpyrazone 200 mg Tablet0.31USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)136-137 °CPhysProp
water solubility31.2 mg/LNot Available
logP2.30HANSCH,C ET AL. (1995)
pKa3.25SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.323 mg/mLALOGPS
logP2.92ALOGPS
logP3.19ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.41ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area57.69 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity113.62 m3·mol-1ChemAxon
Polarizability42.15 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9961
Blood Brain Barrier+0.9776
Caco-2 permeable-0.5583
P-glycoprotein substrateNon-substrate0.9163
P-glycoprotein inhibitor INon-inhibitor0.858
P-glycoprotein inhibitor IINon-inhibitor0.6257
Renal organic cation transporterNon-inhibitor0.8111
CYP450 2C9 substrateNon-substrate0.5504
CYP450 2D6 substrateNon-substrate0.8878
CYP450 3A4 substrateSubstrate0.5146
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6332
Ames testNon AMES toxic0.6195
CarcinogenicityNon-carcinogens0.6932
BiodegradationNot ready biodegradable0.9577
Rat acute toxicity3.0218 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9712
hERG inhibition (predictor II)Non-inhibitor0.8418
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a6r-0591500000-4b27d64be1dee69f96e6
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0002900000-472e293a011d716bb5a8
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0550-2930000000-70abc4e49a7459cc1980

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenyl sulfoxides. These are organosulfur compounds containing a sulfoxide group substituted with a phenyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenyl sulfoxides
Direct Parent
Phenyl sulfoxides
Alternative Parents
Pyrazolidinones / 1,3-dicarbonyl compounds / Sulfoxides / Carboxylic acid hydrazides / Sulfinyl compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Phenyl sulfoxide / Pyrazolidinone / 1,3-dicarbonyl compound / Pyrazolidine / Carboxylic acid hydrazide / Sulfoxide / Carboxylic acid derivative / Azacycle / Organoheterocyclic compound / Sulfinyl compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfoxide, pyrazolidines (CHEBI:9342)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Evers R, de Haas M, Sparidans R, Beijnen J, Wielinga PR, Lankelma J, Borst P: Vinblastine and sulfinpyrazone export by the multidrug resistance protein MRP2 is associated with glutathione export. Br J Cancer. 2000 Aug;83(3):375-83. [PubMed:10917554]
  2. Morrow CS, Smitherman PK, Diah SK, Schneider E, Townsend AJ: Coordinated action of glutathione S-transferases (GSTs) and multidrug resistance protein 1 (MRP1) in antineoplastic drug detoxification. Mechanism of GST A1-1- and MRP1-associated resistance to chlorambucil in MCF7 breast carcinoma cells. J Biol Chem. 1998 Aug 7;273(32):20114-20. [PubMed:9685354]
  3. Bakos E, Evers R, Sinko E, Varadi A, Borst P, Sarkadi B: Interactions of the human multidrug resistance proteins MRP1 and MRP2 with organic anions. Mol Pharmacol. 2000 Apr;57(4):760-8. [PubMed:10727523]
  4. Depeille P, Cuq P, Mary S, Passagne I, Evrard A, Cupissol D, Vian L: Glutathione S-transferase M1 and multidrug resistance protein 1 act in synergy to protect melanoma cells from vincristine effects. Mol Pharmacol. 2004 Apr;65(4):897-905. [PubMed:15044619]
  5. Raggers RJ, van Helvoort A, Evers R, van Meer G: The human multidrug resistance protein MRP1 translocates sphingolipid analogs across the plasma membrane. J Cell Sci. 1999 Feb;112 ( Pt 3):415-22. [PubMed:9885294]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Bakos E, Evers R, Sinko E, Varadi A, Borst P, Sarkadi B: Interactions of the human multidrug resistance proteins MRP1 and MRP2 with organic anions. Mol Pharmacol. 2000 Apr;57(4):760-8. [PubMed:10727523]
  2. Evers R, de Haas M, Sparidans R, Beijnen J, Wielinga PR, Lankelma J, Borst P: Vinblastine and sulfinpyrazone export by the multidrug resistance protein MRP2 is associated with glutathione export. Br J Cancer. 2000 Aug;83(3):375-83. [PubMed:10917554]
  3. Morrow CS, Smitherman PK, Townsend AJ: Role of multidrug-resistance protein 2 in glutathione S-transferase P1-1-mediated resistance to 4-nitroquinoline 1-oxide toxicities in HepG2 cells. Mol Carcinog. 2000 Nov;29(3):170-8. [PubMed:11108662]
  4. Ito K, Oleschuk CJ, Westlake C, Vasa MZ, Deeley RG, Cole SP: Mutation of Trp1254 in the multispecific organic anion transporter, multidrug resistance protein 2 (MRP2) (ABCC2), alters substrate specificity and results in loss of methotrexate transport activity. J Biol Chem. 2001 Oct 12;276(41):38108-14. Epub 2001 Aug 10. [PubMed:11500505]
  5. Flanagan SD, Cummins CL, Susanto M, Liu X, Takahashi LH, Benet LZ: Comparison of furosemide and vinblastine secretion from cell lines overexpressing multidrug resistance protein (P-glycoprotein) and multidrug resistance-associated proteins (MRP1 and MRP2). Pharmacology. 2002;64(3):126-34. [PubMed:11834888]
  6. Hagos Y, Stein D, Ugele B, Burckhardt G, Bahn A: Human renal organic anion transporter 4 operates as an asymmetric urate transporter. J Am Soc Nephrol. 2007 Feb;18(2):430-9. Epub 2007 Jan 17. [PubMed:17229912]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Urate transmembrane transporter activity
Specific Function
Required for efficient urate re-absorption in the kidney. Regulates blood urate levels. Mediates saturable urate uptake by facilitating the exchange of urate against organic anions.
Gene Name
SLC22A12
Uniprot ID
Q96S37
Uniprot Name
Solute carrier family 22 member 12
Molecular Weight
59629.57 Da
References
  1. Shin HJ, Takeda M, Enomoto A, Fujimura M, Miyazaki H, Anzai N, Endou H: Interactions of urate transporter URAT1 in human kidney with uricosuric drugs. Nephrology (Carlton). 2011 Feb;16(2):156-62. doi: 10.1111/j.1440-1797.2010.01368.x. [PubMed:21272127]
  2. Tan PK, Ostertag TM, Miner JN: Mechanism of high affinity inhibition of the human urate transporter URAT1. Sci Rep. 2016 Oct 7;6:34995. doi: 10.1038/srep34995. [PubMed:27713539]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Activator
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Faucette SR, Wang H, Hamilton GA, Jolley SL, Gilbert D, Lindley C, Yan B, Negishi M, LeCluyse EL: Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers. Drug Metab Dispos. 2004 Mar;32(3):348-58. [PubMed:14977870]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
No
General Function
Transporter activity
Specific Function
FABP are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters. FABP2 is probably involved in triglyceride-rich lipoprotein synthesis. Binds satu...
Gene Name
FABP2
Uniprot ID
P12104
Uniprot Name
Fatty acid-binding protein, intestinal
Molecular Weight
15207.165 Da
References
  1. Rowland A, Knights KM, Mackenzie PI, Miners JO: Characterization of the binding of drugs to human intestinal fatty acid binding protein (IFABP): potential role of IFABP as an alternative to albumin for in vitro-in vivo extrapolation of drug kinetic parameters. Drug Metab Dispos. 2009 Jul;37(7):1395-403. doi: 10.1124/dmd.109.027656. Epub 2009 Apr 27. [PubMed:19398502]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocyte...
Gene Name
ABCC3
Uniprot ID
O15438
Uniprot Name
Canalicular multispecific organic anion transporter 2
Molecular Weight
169341.14 Da
References
  1. Zelcer N, Saeki T, Reid G, Beijnen JH, Borst P: Characterization of drug transport by the human multidrug resistance protein 3 (ABCC3). J Biol Chem. 2001 Dec 7;276(49):46400-7. [PubMed:11581266]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
References
  1. Chen ZS, Lee K, Walther S, Raftogianis RB, Kuwano M, Zeng H, Kruh GD: Analysis of methotrexate and folate transport by multidrug resistance protein 4 (ABCC4): MRP4 is a component of the methotrexate efflux system. Cancer Res. 2002 Jun 1;62(11):3144-50. [PubMed:12036927]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Acts as a multispecific organic anion pump which can transport nucleotide analogs.
Gene Name
ABCC5
Uniprot ID
O15440
Uniprot Name
Multidrug resistance-associated protein 5
Molecular Weight
160658.8 Da
References
  1. Wijnholds J, Mol CA, van Deemter L, de Haas M, Scheffer GL, Baas F, Beijnen JH, Scheper RJ, Hatse S, De Clercq E, Balzarini J, Borst P: Multidrug-resistance protein 5 is a multispecific organic anion transporter able to transport nucleotide analogs. Proc Natl Acad Sci U S A. 2000 Jun 20;97(13):7476-81. [PubMed:10840050]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Isoform 1: May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Transports glutathione conjugates as leukotriene-c4 (LTC4...
Gene Name
ABCC6
Uniprot ID
O95255
Uniprot Name
Multidrug resistance-associated protein 6
Molecular Weight
164904.81 Da
References
  1. Chen ZS, Hopper-Borge E, Belinsky MG, Shchaveleva I, Kotova E, Kruh GD: Characterization of the transport properties of human multidrug resistance protein 7 (MRP7, ABCC10). Mol Pharmacol. 2003 Feb;63(2):351-8. [PubMed:12527806]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Honda Y, Ushigome F, Koyabu N, Morimoto S, Shoyama Y, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Effects of grapefruit juice and orange juice components on P-glycoprotein- and MRP2-mediated drug efflux. Br J Pharmacol. 2004 Dec;143(7):856-64. Epub 2004 Oct 25. [PubMed:15504753]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Evers R, de Haas M, Sparidans R, Beijnen J, Wielinga PR, Lankelma J, Borst P: Vinblastine and sulfinpyrazone export by the multidrug resistance protein MRP2 is associated with glutathione export. Br J Cancer. 2000 Aug;83(3):375-83. [PubMed:10917554]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Flanagan SD, Cummins CL, Susanto M, Liu X, Takahashi LH, Benet LZ: Comparison of furosemide and vinblastine secretion from cell lines overexpressing multidrug resistance protein (P-glycoprotein) and multidrug resistance-associated proteins (MRP1 and MRP2). Pharmacology. 2002;64(3):126-34. [PubMed:11834888]
  2. Evers R, de Haas M, Sparidans R, Beijnen J, Wielinga PR, Lankelma J, Borst P: Vinblastine and sulfinpyrazone export by the multidrug resistance protein MRP2 is associated with glutathione export. Br J Cancer. 2000 Aug;83(3):375-83. [PubMed:10917554]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2017 17:18