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

General Information of Drug (ID: DR0120)
Drug Name
Antipyrine
Synonyms
Analgesine; Anodynin; Anodynine; Antipirin; Antipyrin; Antipyrinum; Apirelina; Auralgan; Azophen; Azophene; Azophenum; Dimethyloxychinizin; Dimethyloxyquinazine; Fenazon; Fenazon [Czech]; Fenazona; Fenazona [INN-Spanish]; Fenazone; Methozin; Oxydimethylquinazine; Oxydimethylquinizine; Parodyne; Phenazon; Phenazone; Phenazone (pharmaceutical); Phenazonum; Phenozone; Phenylon; Phenylone; Pyrazophyl; Sedatin; Sedatine; antipyrine; 2,3-Dimethyl-1-phenyl-5-pyrazolone; 3-Antipyrine; 3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-; 60-80-0
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 188.23 Topological Polar Surface Area 23.6
Heavy Atom Count 14 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
2206
PubChem SID
73701 ; 585988 ; 609733 ; 897396 ; 3132034 ; 7548402 ; 7848839 ; 8149206 ; 8151497 ; 10321128 ; 10529438 ; 11112159 ; 11335659 ; 11360898 ; 11362852 ; 11365414 ; 11367976 ; 11371470 ; 11373763 ; 11376138 ; 11461870 ; 11466057 ; 11467177 ; 11483752 ; 11485754 ; 11487904 ; 11490121 ; 11491967 ; 11493872 ; 11533957 ; 14797281 ; 24846783 ; 24890859 ; 24891029 ; 26611611 ; 26679445 ; 26747866 ; 26747867 ; 26753718 ; 29221384 ; 32867460 ; 46505216 ; 47216735 ; 47291090 ; 47515275 ; 47662233 ; 47885364 ; 47959690 ; 48259186 ; 48414294
ChEBI ID
ChEBI:31225
CAS Number
60-80-0
TTD Drug ID
D03IRR
Formula
C11H12N2O
Canonical SMILES
CC1=CC(=O)N(N1C)C2=CC=CC=C2
InChI
1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3
InChIKey
VEQOALNAAJBPNY-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
3-OH-methylantipyrine DM006889 N. A. Oxidation - Hydrolyzationn 1 [2]
4-OH-antipyrine DM006888 N. A. Oxidation - Hydrolyzationn 1 [2]
Norantipyrine DM006887
4021
Unclear 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007486 Antipyrine Norantipyrine Unclear CYP2C8 ... [2]
MR007487 Antipyrine 4-OH-antipyrine Oxidation - Hydrolyzationn CYP3A4 ... [2]
MR007488 Antipyrine 3-OH-methylantipyrine Oxidation - Hydrolyzationn CYP1A2 ... [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
RNA cytidine acetyltransferase (hALP) DME0007 Homo sapiens
NAT10_HUMAN
2.3.1.5
[5]
⏷ Show the Full List of 11  DME(s)
References
1 Pharmacokinetic and pharmacodynamic aspects of the ideal COX-2 inhibitor: a pharmacologist's perspective. Clin Exp Rheumatol. 2001 Nov-Dec;19(6 Suppl 25):S51-7.
2 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
3 Identification of the human hepatic cytochromes P450 involved in the in vitro oxidation of antipyrine. Drug Metab Dispos. 1996 Apr;24(4):487-94.
4 Orphenadrine and methimazole inhibit multiple cytochrome P450 enzymes in human liver microsomes. Drug Metab Dispos. 1997 Mar;25(3):390-3.
5 Evaluation of the influence of diabetes mellitus on antipyrine metabolism and CYP1A2 and CYP2D6 activity. Pharmacotherapy. 2000 Feb;20(2):182-90.

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