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

Details

Stereochemistry RACEMIC
Molecular Formula C23H20N2O3S
Molecular Weight 404.482
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFINPYRAZONE

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

HIDE SMILES / InChI

Description
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.

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

-3.35836807E11
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
n = 1
Health Status: healthy
Age Group: 24
Sex: M
Population Size: 1
Sources:
Other AEs: Acute renal failure...
Other AEs:
Acute renal failure
Sources:
1000 mg multiple, oral (max)
Recommended
Dose: 1000 mg
Route: oral
Route: multiple
Dose: 1000 mg
Sources: Page: p.2
unhealthy
Health Status: unhealthy
Condition: Thrombosis
Sources: Page: p.2
Other AEs: Acute renal failure...
Other AEs:
Acute renal failure (low incidence)
Sources: Page: p.2
400 mg 2 times / day multiple, oral (max)
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Gouty arthritis
Sources: Page: p.4
Disc. AE: Skin rash...
AEs leading to
discontinuation/dose reduction:
Skin rash (rare)
Sources: Page: p.4
AEs

AEs

AESignificanceDosePopulation
Acute renal failure
1000 mg single, oral
Overdose
Dose: 1000 mg
Route: oral
Route: single
Dose: 1000 mg
Sources:
healthy, 24
n = 1
Health Status: healthy
Age Group: 24
Sex: M
Population Size: 1
Sources:
Acute renal failure low incidence
1000 mg multiple, oral (max)
Recommended
Dose: 1000 mg
Route: oral
Route: multiple
Dose: 1000 mg
Sources: Page: p.2
unhealthy
Health Status: unhealthy
Condition: Thrombosis
Sources: Page: p.2
Skin rash rare
Disc. AE
400 mg 2 times / day multiple, oral (max)
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Gouty arthritis
Sources: Page: p.4
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
Abnormalities of urinary sediment and renal failure following sulfinpyrazone therapy.
1976 Sep
[Sulfinpyrazone-associated renal failure (author's transl)].
1982 Jul 9
Interaction of sulfonamide and sulfone compounds with Toxoplasma gondii dihydropteroate synthase.
1990 Feb
A reporter gene assay to assess the molecular mechanisms of xenobiotic-dependent induction of the human CYP3A4 gene in vitro.
1999 Mar
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
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 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
Sulfinpyrazone (2.5 mM) inhibited the MRP5-mediated PMEA efflux from resistant 293/MRP5 cells
Name Type Language
SULFINPYRAZONE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
sulfinpyrazone [INN]
Common Name English
SULFINPYRAZONE [VANDF]
Common Name English
ANTURANE
Brand Name English
SULFINPYRAZONE [MI]
Common Name English
NSC-75925
Code English
SULFINPYRAZONE [EP IMPURITY]
Common Name 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
Sulfinpyrazone [WHO-DD]
Common Name English
SULPHINPYRAZONE
Common Name English
SULFINPYRAZONE [MART.]
Common Name English
SULFINPYRAZONE [USP-RS]
Common Name English
SULFINPYRAZONE [ORANGE BOOK]
Common Name English
SULFINPYRAZONE [USP IMPURITY]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C921
Created by admin on Fri Dec 15 18:46:20 UTC 2023 , Edited by admin on Fri Dec 15 18:46:20 UTC 2023
WHO-ATC M04AB02
Created by admin on Fri Dec 15 18:46:20 UTC 2023 , Edited by admin on Fri Dec 15 18:46:20 UTC 2023
LIVERTOX 913
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WHO-VATC QM04AB02
Created by admin on Fri Dec 15 18:46:20 UTC 2023 , Edited by admin on Fri Dec 15 18:46:20 UTC 2023
Code System Code Type Description
PUBCHEM
5342
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PRIMARY
CHEBI
9342
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PRIMARY
INN
777
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PRIMARY
ChEMBL
CHEMBL832
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PRIMARY
FDA UNII
V6OFU47K3W
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PRIMARY
ECHA (EC/EINECS)
200-357-4
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PRIMARY
EPA CompTox
DTXSID0023618
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PRIMARY
EVMPD
SUB10737MIG
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PRIMARY
NCI_THESAURUS
C47739
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PRIMARY
CAS
57-96-5
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PRIMARY
SMS_ID
100000091951
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PRIMARY
DRUG BANK
DB01138
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PRIMARY
MESH
D013442
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PRIMARY
MERCK INDEX
m10349
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PRIMARY Merck Index
IUPHAR
5826
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PRIMARY
HSDB
3396
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PRIMARY
RXCUI
10205
Created by admin on Fri Dec 15 18:46:20 UTC 2023 , Edited by admin on Fri Dec 15 18:46:20 UTC 2023
PRIMARY RxNorm
WIKIPEDIA
SULFINPYRAZONE
Created by admin on Fri Dec 15 18:46:20 UTC 2023 , Edited by admin on Fri Dec 15 18:46:20 UTC 2023
PRIMARY
NSC
75925
Created by admin on Fri Dec 15 18:46:20 UTC 2023 , Edited by admin on Fri Dec 15 18:46:20 UTC 2023
PRIMARY
RS_ITEM_NUM
1637008
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PRIMARY
DRUG CENTRAL
2528
Created by admin on Fri Dec 15 18:46:20 UTC 2023 , Edited by admin on Fri Dec 15 18:46:20 UTC 2023
PRIMARY