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

General Information of Drug (ID: DR1281)
Drug Name
Phenylbutazone
Synonyms
Phebuzin; Phenbutazol; Phenylbutaz; Phenylbutazonum; Praecirheumin; Pyrabutol; Pyrazolidin; Reumasyl; Reumazin; Reumazol; Reumuzol; Alkabutazona; Artrizin; Butacote; Butadion; Butalgina; Butapirazol; Butapirazole; Butapyrazole; Butazolidin; Butazolidine; Butylpyrin; Chembutazone; Diphenylbutazone; Ecobutazone; Fenibutal; Fenibutazona; Fenilbutazona; Fenylbutazon; Intalbut; Intrabutazone; Intrazone; Ipsoflame; Mephabutazon; Mephabutazone; Nadozone; Novophenyl; Scanbutazone; phenylbutazone; 4-Butyl-1,2-diphenylpyrazolidine-3,5-dione; 50-33-9; Bute
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 308.4 Topological Polar Surface Area 40.6
Heavy Atom Count 23 Rotatable Bond Count 5
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
4781
PubChem SID
9644 ; 86400 ; 589070 ; 855958 ; 3138358 ; 5292420 ; 7847576 ; 7889660 ; 7980302 ; 8027936 ; 8027956 ; 8027959 ; 8149478 ; 8152935 ; 10524351 ; 11109641 ; 11111674 ; 11335506 ; 11360745 ; 11363973 ; 11366535 ; 11369097 ; 11371689 ; 11374093 ; 11377259 ; 11461717 ; 11485019 ; 11489098 ; 11490491 ; 11492292 ; 11494893 ; 14898740 ; 17389760 ; 17405551 ; 24277729 ; 24424563 ; 26536476 ; 26611871 ; 26680142 ; 26747057 ; 26747058 ; 26751573 ; 29223865 ; 46507038 ; 47216692 ; 47440165 ; 47515230 ; 47736386 ; 47736387 ; 48414314
ChEBI ID
CHEBI:48574
CAS Number
50-33-9
TTD Drug ID
D07VHR
Formula
C19H20N2O2
Canonical SMILES
CCCCC1C(=O)N(N(C1=O)C2=CC=CC=C2)C3=CC=CC=C3
InChI
1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3
InChIKey
VYMDGNCVAMGZFE-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-hydroxyphenylbutazone DM001246
101102
Oxidation - Oxidation 1 [4]
Beta-hydroxyphenylbutazone DM001244 N. A. Oxidation - Oxidation 1 [4]
Gamma-hydroxyphenylbutazone DM001243
120741
Oxidation - Oxidation 1 [5]
Glucuronides of phenylbutazone DM001247 N. A. Conjugation - Glucuronidation 1 [3]
Oxyphenbutazone DM001242
4641
Oxidation - Oxidation 1 [5]
P,gamma-dihydroxyphenylbutazone DM001245 N. A. Oxidation - Oxidation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002872 Phenylbutazone Oxyphenbutazone Oxidation - Oxidation CYP2C9 [5]
MR002873 Phenylbutazone Gamma-hydroxyphenylbutazone Oxidation - Oxidation CYP2C9 [5]
MR002874 Phenylbutazone Beta-hydroxyphenylbutazone Oxidation - Oxidation CYP2C9 [4]
MR002875 Phenylbutazone P,gamma-dihydroxyphenylbutazone Oxidation - Oxidation CYP2C9 [4]
MR002876 Phenylbutazone 4-hydroxyphenylbutazone Oxidation - Oxidation CYP2C9 [4]
MR002877 Phenylbutazone Glucuronides of phenylbutazone Conjugation - Glucuronidation UGT1A9 [3]
⏷ 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 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
References
1 Phenylbutazone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Metabolism of sulfinpyrazone sulfide and sulfinpyrazone by human liver microsomes and cDNA-expressed cytochrome P450s. Drug Metab Dispos. 2001 May;29(5):701-11.
3 Identification of human UDP-glucuronosyltransferase isoform(s) responsible for the C-glucuronidation of phenylbutazone. Arch Biochem Biophys. 2006 Oct 1;454(1):72-9.
4 McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 1999. Bethesda, MD:American Society of Health-System Pharmacists, Inc. 1999 (Plus Supplements)., p. 1760
5 The Analysis of Phenylbutazone and Its Active Metabolite, Oxyphenbutazone, in Equine Tissues (Muscle, Kidney, and Liver), Urine, and Serum by LC-MS/MS

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