ChemFOnt: Showing chemical card for Sulfinpyrazone (CFc000009552)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:43 UTC

Chemfont ID

CFc000009552

Molecule Identification

Common Name

Sulfinpyrazone

Definition

Sulfinpyrazone is only found in individuals that have used or taken this drug. It is a uricosuric drug that is used to reduce the serum urate levels in gout therapy. It lacks anti-inflammatory, analgesic, and diuretic properties. [PubChem]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).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Diphenyl-3,5-dioxo-4-(2-phenylsulfinylethyl)pyrazolidine	ChEBI
1,2-Diphenyl-4-(2'-phenylsulfinethyl)-3,5-pyrazolidinedione	ChEBI
4-(2-Benzenesulfinylethyl)-1,2-diphenylpyrazolidine-3,5-dione	ChEBI
Anturane	ChEBI
Sulfoxyphenylpyrazolidine	ChEBI
1,2-Diphenyl-3,5-dioxo-4-(2-phenylsulphinylethyl)pyrazolidine	Generator
1,2-Diphenyl-4-(2'-phenylsulphinethyl)-3,5-pyrazolidinedione	Generator
4-(2-Benzenesulphinylethyl)-1,2-diphenylpyrazolidine-3,5-dione	Generator
Sulphoxyphenylpyrazolidine	Generator
Sulphinpyrazone	Generator
Diphenylpyrazone	HMDB
Sulfinpyrazine	HMDB
Sulfinpyrazon	HMDB
Usaf ge-13	HMDB
Apo sulfinpyrazone	HMDB
Nu pharm brand OF sulfinpyrazone	HMDB
Nu sulfinpyrazone	HMDB
Nu-pharm brand OF sulfinpyrazone	HMDB
Nu-sulfinpyrazone	HMDB
Sulfoxyphenylpyrazolidin	HMDB
Anturan	HMDB
Apo-sulfinpyrazone	HMDB
Apotex brand OF sulfinpyrazone	HMDB
Novartis brand OF sulfinpyrazone	HMDB

Chemical Formula

C₂₃H₂₀N₂O₃S

Average Molecular Weight

404.482

Monoisotopic Molecular Weight

404.119463206

IUPAC Name

4-[2-(benzenesulfinyl)ethyl]-1,2-diphenylpyrazolidine-3,5-dione

Traditional Name

sulfinpyrazone

CAS Registry Number

57-96-5

SMILES

O=C1C(CCS(=O)C2=CC=CC=C2)C(=O)N(N1C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

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

InChI Key

MBGGBVCUIVRRBF-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

Phenyl sulfoxide
Pyrazolidinone
1,3-dicarbonyl compound
Pyrazolidine
Carboxylic acid hydrazide
Sulfoxide
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Sulfinyl compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfoxide (CHEBI:9342 )
pyrazolidines (CHEBI:9342 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015269)
Membrane (HMDB: HMDB0015269)

Source

Exogenous

Exogenous (HMDB: HMDB0015269)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	2.92	ALOGPS
logP	3.19	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.41	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.69 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	113.62 m³·mol⁻¹	ChemAxon
Polarizability	42.15 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon