U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C23H20N2O3S
Molecular Weight 404.4834
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFINPYRAZONE

SMILES

c1ccc(cc1)N2C(=O)C(CCS(=O)c3ccccc3)C(=O)N2c4ccccc4

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

HIDE SMILES / InChI

Molecular Formula C23H20N2O3S
Molecular Weight 404.4834
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: 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.

Originator

Curator's Comment:: was developed and marketed as Anturane® by Novartis. # Novartis

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Anturane

Approved Use

Anturane is indicated for the treatment of: Chronic gouty arthritis Intermittent gouty arthritis

Launch Date

-335836800000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
13.4 mg/L
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
26 mg/L
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
2.2 mg/L
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
53 mg × h/L
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
191.9 μg × h/mL
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
116 mg × h/L
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
79.6 μg × h/mL
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
13.4 mg × h/L
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
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
16.5 μg × h/mL
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
5.7 μg × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9.96 h
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
4.17 h
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
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
3.79 h
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
3.6 h
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
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
3.8 h
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

Doses

DosePopulationAdverse events​
1000 mg single, oral
Overdose
Dose: 1000 mg
Route: oral
Route: single
Dose: 1000 mg
Sources:
healthy, 24
Health Status: healthy
Age Group: 24
Sex: M
Sources:
Other AEs: Acute renal failure...
Other AEs:
Acute renal failure
Sources:
1000 mg multiple, oral
Recommended
Dose: 1000 mg
Route: oral
Route: multiple
Dose: 1000 mg
Sources:
unhealthy
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
Disc. AE: Skin rash...
AEs leading to
discontinuation/dose reduction:
Skin rash (rare)
Sources:
AEs

AEs

AESignificanceDosePopulation
Acute renal failure
1000 mg single, oral
Overdose
Dose: 1000 mg
Route: oral
Route: single
Dose: 1000 mg
Sources:
healthy, 24
Health Status: healthy
Age Group: 24
Sex: M
Sources:
Acute renal failure low incidence
1000 mg multiple, oral
Recommended
Dose: 1000 mg
Route: oral
Route: multiple
Dose: 1000 mg
Sources:
unhealthy
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
weak
yes [IC50 103 uM]
yes [IC50 11 uM]
yes [IC50 158 uM]
yes [IC50 16 uM]
yes [IC50 187 uM]
yes [IC50 267 uM]
yes [IC50 2741 uM]
yes [IC50 402 uM]
yes [IC50 420 uM]
yes [IC50 46 uM]
yes [IC50 58 uM]
yes [IC50 651 uM]
yes [Ki 230 uM]
yes
yes
yes
yes
yes
PubMed

PubMed

TitleDatePubMed
Are agents affecting platelet functions clinically useful?
1976 Dec
Acute myelomonocytic leukaemia and multiple myeloma after sulphinpyrazone and colchicine treatment of gout.
1976 Jul 10
[Acute renal failure induced by sulfinpyrazone (author's transl)].
1981
Acute renal dysfunction due to sulfinpyrazone therapy in post-myocardial infarction cardiomegaly: reversible hypersensitive interstitial nephritis.
1981 Aug
Sulphinpyrazone-induced acute renal failure.
1981 Feb 21
Sulfinpyrazone induced uric acid urolithiasis with acute renal failure.
1981 Jul
Effects of sulfinpyrazone, aspirin and propranolol on the isoproterenol-induced myocardial necrosis.
1981 Jul
Renal dysfunction due to anturan.
1981 Jul 9
Renal dysfunction due to anturane.
1981 Nov 5
Sulphinpyrazone--induced decrease in renal function: a review of reports with discussion of pathogenesis.
1982
Acute renal failure following sulfinpyrazone therapy.
1982 Apr
[Sulfinpyrazone-associated renal failure (author's transl)].
1982 Jul 9
Non oliguric acute renal failure after treatment with sulfinpyrazone.
1982 May
Transcoronary platelet thromboxane A2 formation without platelet trapping in patients with coronary stenosis-effect of sulphinpyrazone treatment.
1983 Dec 30
Sulfinpyrazone-associated acute renal failure.
1983 Jul
[Acute interstitial nephritis and kidney failure requiring dialysis after sulfinpyrazone therapy].
1984
Sulfinpyrazone: risk for renal insufficiency.
1984 Mar
[Acute tubulo-interstitial nephropathy associated with ingestion of sulfinpyrazone].
1985 Feb 23
Interaction of sulfonamide and sulfone compounds with Toxoplasma gondii dihydropteroate synthase.
1990 Feb
Comparison of furosemide and vinblastine secretion from cell lines overexpressing multidrug resistance protein (P-glycoprotein) and multidrug resistance-associated proteins (MRP1 and MRP2).
2002
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
Functional expression of the multidrug resistance protein 1 in microglia.
2003 Oct
Glutathione S-transferase M1 and multidrug resistance protein 1 act in synergy to protect melanoma cells from vincristine effects.
2004 Apr
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 Jan
Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers.
2004 Mar
Combined effects of GSTP1 and MRP1 in melanoma drug resistance.
2005 Jul 25
High-throughput screening with HyperCyt flow cytometry to detect small molecule formylpeptide receptor ligands.
2005 Jun
Prediction of CYP2C9-mediated drug-drug interactions: a comparison using data from recombinant enzymes and human hepatocytes.
2005 Nov
Use of immortalized human hepatocytes to predict the magnitude of clinical drug-drug interactions caused by CYP3A4 induction.
2006 Oct
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
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 Jun
HepaRG cells as an in vitro model for evaluation of cytochrome P450 induction in humans.
2008 Jan
Interactions of urate transporter URAT1 in human kidney with uricosuric drugs.
2011 Feb
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).
2013 Dec
Patents

Sample Use Guides

In Vivo Use Guide
Initial
Route of Administration: Oral
Sulfinpyrazone (2.5 mM) inhibited the MRP5-mediated PMEA efflux from resistant 293/MRP5 cells
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:16:10 UTC 2021
Edited
by admin
on Fri Jun 25 21:16:10 UTC 2021
Record UNII
V6OFU47K3W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULFINPYRAZONE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
SULFINPYRAZONE [WHO-DD]
Common Name English
SULFINPYRAZONE [INN]
Common Name English
SULFINPYRAZONE [EP]
Common Name English
SULFINPYRAZONE [USP]
Common Name English
SULFINPYRAZONE [VANDF]
Common Name English
ANTURANE
Brand Name English
SULFINPYRAZONE [MI]
Common Name English
NSC-75925
Code English
1,2-DIPHENYL-4-(2-(PHENYLSULFINYL)ETHYL)-3,5-PYRAZOLIDINEDIONE
Systematic Name English
SULFINPYRAZONE [EP MONOGRAPH]
Common Name English
3,5-PYRAZOLIDINEDIONE, 1,2-DIPHENYL-4-(2-(PHENYLSULFINYL)ETHYL)-
Systematic Name English
SULFINPYRAZONE [JAN]
Common Name English
SULPHINPYRAZONE
Common Name English
SULFINPYRAZONE [MART.]
Common Name English
SULFINPYRAZONE [USP-RS]
Common Name English
SULFINPYRAZONE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C921
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
WHO-ATC M04AB02
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
LIVERTOX 913
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
WHO-VATC QM04AB02
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
Code System Code Type Description
PUBCHEM
5342
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY
INN
777
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY
ChEMBL
CHEMBL832
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY
FDA UNII
V6OFU47K3W
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-357-4
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY
EPA CompTox
57-96-5
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY
EVMPD
SUB10737MIG
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY
NCI_THESAURUS
C47739
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY
CAS
57-96-5
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY
DRUG BANK
DB01138
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY
MESH
D013442
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY
MERCK INDEX
M10349
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY Merck Index
USP_CATALOG
1637008
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY USP-RS
IUPHAR
5826
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY
HSDB
3396
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY
RXCUI
10205
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
SULFINPYRAZONE
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY
DRUG CENTRAL
2528
Created by admin on Fri Jun 25 21:16:10 UTC 2021 , Edited by admin on Fri Jun 25 21:16:10 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> INDUCER
METABOLIC ENZYME -> INDUCER
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC