Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1515)
Drug Name
Sulfinpyrazone
Synonyms
Sulfinpirazona [INN-Spanish]; Sulfinpyrazine; Sulfinpyrazon; Sulfinpyrazonum; Sulfinpyrazonum [INN-Latin]; Sulfoxyphenylpyrazolidine; Sulphinpyrazone; USAF GE-13; Anturan; Anturane; Anturane (TN); Anturanil; Anturano; Anturen; Anturidin; Apo-Sulfinpyrazone; Diphenylpyrazone; Enturan; Enturen; sulfinpyrazone; (+/-)-SULFINPYRAZONE; 1,2-Diphenyl-4-(2-(phenylsulfinyl)ethyl)pyrazolidine-3,5-dione; 4-(Phenylsulfoxyethyl)-1,2-diphenyl-3,5-pyrazolidinedione; 57-96-5; G 28315; NSC 75925
Indication Uncontrolled gout [ICD11: FA25] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 404.5 Topological Polar Surface Area 76.9
Heavy Atom Count 29 Rotatable Bond Count 6
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5342
PubChem SID
9525 ; 117338 ; 611476 ; 855982 ; 5632696 ; 7847515 ; 8149541 ; 8153281 ; 10321460 ; 11112139 ; 11335265 ; 11360504 ; 11363916 ; 11366478 ; 11369040 ; 11371640 ; 11374587 ; 11377202 ; 11461476 ; 11466318 ; 11467438 ; 11485183 ; 11486155 ; 11489140 ; 11490406 ; 11492660 ; 11494836 ; 14718483 ; 14879380 ; 24899841 ; 26611933 ; 26680609 ; 26747070 ; 26747071 ; 29224394 ; 46500625 ; 46504918 ; 47216628 ; 47290983 ; 47290984 ; 47440092 ; 47588838 ; 48110300 ; 48334323 ; 48416577 ; 49698736 ; 50029653 ; 50100985 ; 50661502 ; 53789714
ChEBI ID
ChEBI:9342
CAS Number
57-96-5
TTD Drug ID
D03DEI
Formula
C23H20N2O3S
Canonical SMILES
C1=CC=C(C=C1)N2C(=O)C(C(=O)N2C3=CC=CC=C3)CCS(=O)C4=CC=CC=C4
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
InChIKey
MBGGBVCUIVRRBF-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
4-hydroxy-sulfinpyrazone DM000388
69619356
Oxidation - Hydroxylation 1 [5]
p-hydroxy sulfinpyrazone DM000382
161594
Oxidation - Hydroxylation 1 [6] , [5]
Sulfinpyrazone sulfone DM000385
70676
Oxidation - Oxidation 1 [6]
Sulphide DM000386
77327
Oxidation - Oxidation 1 [5]
p-hydroxy sulfinpyrazone Sulphide DM000383
3081954
Oxidation - Oxidation 2 [5]
p-hydroxy sulfinpyrazone Sulphone DM000384
21524471
Oxidation - Oxidation 3 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003413 Sulfinpyrazone p-hydroxy sulfinpyrazone Oxidation - Hydroxylation Unclear [6], [5]
MR003414 Sulfinpyrazone Sulfinpyrazone sulfone Oxidation - Oxidation CYP3A4 [6]
MR003415 Sulfinpyrazone Sulphide Oxidation - Oxidation Unclear [5]
MR003416 Sulfinpyrazone 4-hydroxy-sulfinpyrazone Oxidation - Hydroxylation Unclear [5]
MR003411 p-hydroxy sulfinpyrazone p-hydroxy sulfinpyrazone Sulphide Oxidation - Oxidation Unclear [5]
MR003412 p-hydroxy sulfinpyrazone Sulphide p-hydroxy sulfinpyrazone Sulphone Oxidation - Oxidation Unclear [5]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1415 Eggerthella lenta Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [4]
⏷ Show the Full List of 9  DME(s)
References
1 Sulfinpyrazone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
3 CYP3A4 induction by drugs: correlation between a pregnane X receptor reporter gene assay and CYP3A4 expression in human hepatocytes. Drug Metab Dispos. 2002 Jul;30(7):795-804.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
5 Species differences in the disposition and metabolism of sulfinpyrazone Xenobiotica. 1981 Aug;11(8):559-68. doi: 10.3109/00498258109045867.
6 Metabolism of sulfinpyrazone sulfide and sulfinpyrazone by human liver microsomes and cDNA-expressed cytochrome P450s. Drug Metab Dispos. 2001 May;29(5):701-11.

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