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

Molecular Formula C23H20N2O3S
Molecular Weight 404.482
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Approval Year

PubMed

PubMed

TitleDatePubMed
Abnormalities of urinary sediment and renal failure following sulfinpyrazone therapy.
1976 Sep
Renal dysfunction due to anturan.
1981 Jul 9
Acute renal failure secondary to sulfinpyrazone treatment after myocardial infarction.
1984
[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
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
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
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
In Vitro Use Guide
Sulfinpyrazone (2.5 mM) inhibited the MRP5-mediated PMEA efflux from resistant 293/MRP5 cells
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:33:08 UTC 2019
Edited
by admin
on Mon Oct 21 20:33:08 UTC 2019
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
3,5-PYRAZOLIDINEDIONE, 1,2-DIPHENYL-4-(2-(PHENYLSULFINYL)ETHYL)-
Systematic Name English
SULFINPYRAZONE [JAN]
Common Name English
SULPHINPYRAZONE
Common Name English
SULFINPYRAZONE [HSDB]
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 Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
WHO-ATC M04AB02
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
LIVERTOX 913
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
WHO-VATC QM04AB02
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
Code System Code Type Description
PUBCHEM
5342
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
PRIMARY
INN
777
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
PRIMARY
ChEMBL
CHEMBL832
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-357-4
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
PRIMARY
EPA CompTox
57-96-5
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
PRIMARY
EVMPD
SUB10737MIG
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
PRIMARY
NCI_THESAURUS
C47739
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
PRIMARY
CAS
57-96-5
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
PRIMARY
DRUG BANK
DB01138
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
PRIMARY
MESH
D013442
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
PRIMARY
MERCK INDEX
M10349
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
PRIMARY Merck Index
IUPHAR
5826
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
PRIMARY
HSDB
57-96-5
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
PRIMARY
RXCUI
10205
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
PRIMARY RxNorm
WIKIPEDIA
SULFINPYRAZONE
Created by admin on Mon Oct 21 20:33:08 UTC 2019 , Edited by admin on Mon Oct 21 20:33:08 UTC 2019
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> INDUCER
TARGET -> INHIBITOR
METABOLIC ENZYME -> INDUCER
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC