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

General Information of Drug (ID: DR1304)
Drug Name
Pirprofen
Synonyms
Pirprofen; Pirprofen (USAN/INN); Pirprofen [USAN:BAN:INN]; Pirprofen [USAN:INN:BAN]; Pirprofene; Pirprofene [INN-French]; Pirprofeno; Pirprofeno [INN-Spanish]; Pirprofenum; Pirprofenum [INN-Latin]; Rengasil; SU 21524; SU-21524; pirprofen[usan:ban:inn]; 3-CHLORO-4-(3-PYRROLIN-1-YL)HYDRATROPIC ACID; 31793-07-4; AC1L1UQD; AC1Q5RRJ; BRN 1686438; Benzeneacetic acid, 3-chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)-alpha-methyl-; C13H14ClNO2; EINECS 250-805-8; Hydratropic acid, 3-chloro-4-(3-pyrrolin-1-yl)-; SCHEMBL24311
Indication Rheumatoid arthritis [ICD11: FA20] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 251.71 Topological Polar Surface Area 40.5
Heavy Atom Count 17 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
35935
ChEBI ID
CHEBI:135028
CAS Number
31793-07-4
TTD Drug ID
D0S9ET
Formula
C13H14ClNO2
Canonical SMILES
CC(C1=CC(=C(C=C1)N2CC=CC2)Cl)C(=O)O
InChI
1S/C13H14ClNO2/c1-9(13(16)17)10-4-5-12(11(14)8-10)15-6-2-3-7-15/h2-5,8-9H,6-7H2,1H3,(H,16,17)
InChIKey
PIDSZXPFGCURGN-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
Amino-metabolite DM004812
13065232
Unclear 1 [3]
Epoxide metabolite DM004808
9881823
Unclear 1 [3]
Pirprofen glucuronide DM007053 N. A. Conjugation - Glucuronidation 1 [3] , [2]
Pyrrole M1 DM004810
3082204
Unclear 1 [3]
Pyrrole metabolite glucuronide DM004811 N. A. Conjugation - Glucuronidation 2 [3]
Pyrrole metabolite glucuronide DM004811 N. A. Unclear 2 [3] , [2]
Trans-diol metabolite DM007051 N. A. Oxidation - Hydrolyzationn 2 [3]
Unclear DM009999 N. A. Conjugation - Glucuronidation 2 [3]
Unclear DM009999 N. A. Unclear 2 [3]
Glucuronide of Trans-diol metabolite DM007052 N. A. Conjugation - Glucuronidation 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005169 Pirprofen Epoxide metabolite Unclear Unclear [3]
MR005172 Pirprofen Pirprofen glucuronide Conjugation - Glucuronidation UGT1A1 [3], [2]
MR005174 Pirprofen Pyrrole M1 Unclear Unclear [3]
MR005176 Pirprofen Amino-metabolite Unclear Unclear [3]
MR005177 Amino-metabolite Unclear Unclear Unclear [3]
MR005170 Epoxide metabolite Trans-diol metabolite Oxidation - Hydrolyzationn Unclear [3]
MR005178 Epoxide metabolite Unclear Conjugation - Glucuronidation Unclear [3]
MR005173 Pirprofen glucuronide Pyrrole metabolite glucuronide Unclear Unclear [3], [2]
MR005175 Pyrrole M1 Pyrrole metabolite glucuronide Conjugation - Glucuronidation Unclear [3]
MR005171 Trans-diol metabolite Glucuronide of Trans-diol metabolite Conjugation - Glucuronidation Unclear [3]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
References
1 Consolidated List of Products - Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or Not Approved by Governments, Twelfth Issue - Pharmaceuticals. United Nations - New York, 2005
2 Glucuronidation of 2-arylpropionic acids pirprofen, flurbiprofen, and ibuprofen by liver microsomes. Drug Metab Dispos. 1990 Sep-Oct;18(5):692-7.
3 High-performance liquid chromatographic determination of pirprofen and five of its metabolites in human plasma without hydrolysis and in human urine before and after chemical hydrolysis

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