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

General Information of Drug (ID: DR1242)
Drug Name
Parecoxib
Prodrug Info Parecoxib is the prodrug of Valdecoxib
Synonyms
Parecoxib; Parecoxib [USAN:INN:BAN]; Parocoxib; Dynastat; SC 69124; SC-69124; Valus-P; Vorth-P; parecoxibum; 9TUW81Y3CE; CHEBI:73038; N-((p-(5-methyl-3-phenyl-4-isoxazolyl)phenyl)sulfonyl)propionamide; N-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonyl]propanamide; N-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylpropanamide; N-{[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonyl}propanamide; Propanamide, N-((4-(5-methyl-3-phenyl-4-isoxazolyl)phenyl)sulfonyl)-; UNII-9TUW81Y3CE
Indication Anaesthesia [ICD11: 8E22] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 370.4 Topological Polar Surface Area 97.6
Heavy Atom Count 26 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
119828
PubChem SID
10238678 ; 14828797 ; 17397807 ; 29300637 ; 49829565 ; 50067919 ; 76546468 ; 99444910 ; 104236927 ; 104409301 ; 129337106 ; 135076077 ; 137039042 ; 137244309 ; 142086609 ; 160969477 ; 162169241 ; 174528197 ; 177749133 ; 178100244 ; 179225992 ; 198980232 ; 210275621 ; 210281280 ; 211536041 ; 223794316 ; 226400424 ; 249867344 ; 252553762
ChEBI ID
CHEBI:73038
CAS Number
198470-84-7
TTD Drug ID
D05UWI
Formula
C19H18N2O4S
Canonical SMILES
CCC(=O)NS(=O)(=O)C1=CC=C(C=C1)C2=C(ON=C2C3=CC=CC=C3)C
InChI
1S/C19H18N2O4S/c1-3-17(22)21-26(23,24)16-11-9-14(10-12-16)18-13(2)25-20-19(18)15-7-5-4-6-8-15/h4-12H,3H2,1-2H3,(H,21,22)
InChIKey
TZRHLKRLEZJVIJ-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
Valdecoxib DM003087
119607
Unclear 1 [3] , [4]
Valdecoxib metabolite M1 DM002428
9818888
Oxidation - Methyl-Hydroxylation 2 [5] , [6]
Valdecoxib metabolite M2 DM002423
11198846
Oxidation - N-Oxidation 2 [6]
Valdecoxib metabolite M9 DM002433
72710738
Oxidation - Hydroxylation 2 [5] , [6]
Valdecoxib N-glucuronide DM002738
145721920
Conjugation - Glucuronidation 2 [5] , [6]
Valdecoxib metabolite M1-G DM002435
156028109
Conjugation - Glucuronidation 3 [6]
Valdecoxib metabolite M2-G DM002434
156028043
Conjugation - Glucuronidation 3 [5] , [6]
Valdecoxib metabolite M3 DM002429 N. A. Oxidation - Hydroxylation 3 [5]
Valdecoxib metabolite M3 DM002429 N. A. Unclear 3 [5]
Valdecoxib metabolite M4 DM002431
19608686
Oxidation - Oxidation 3 [6] , [5]
Valdecoxib metabolite M5 DM002424
156028093
Oxidation - Methyl-Hydroxylation 3 [6]
Valdecoxib metabolite M7 DM002426
17831363
Unclear 3 [5]
Valdecoxib metabolite M9-G DM002436 N. A. Unclear 3 [5] , [6]
Valdecoxib metabolite M3-G DM002430
156028032
Oxidation - S-Oxidation 4 [5]
Valdecoxib metabolite M3-G DM002430
156028032
Oxidation - S-Oxidation 4 [2]
Valdecoxib metabolite M5-G DM002425
155928966
Conjugation - Glucuronidation 4 [6]
Valdecoxib metabolite M6 DM002432
86212053
Unclear 4 [5]
Valdecoxib metabolite M8 DM002427
11565904
Oxidation - S-Oxidation 4 [5]
⏷ Show the Full List of 18  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003479 Parecoxib Valdecoxib Unclear UGT [3], [4]
MR003480 Valdecoxib Valdecoxib metabolite M2 Oxidation - N-Oxidation Unclear [6]
MR003485 Valdecoxib Valdecoxib metabolite M1 Oxidation - Methyl-Hydroxylation CYP3A4 ... [5], [6]
MR003491 Valdecoxib Valdecoxib metabolite M9 Oxidation - Hydroxylation CYP3A4 ... [5], [6]
MR003496 Valdecoxib Valdecoxib N-glucuronide Conjugation - Glucuronidation UGT [5], [6]
MR003486 Valdecoxib metabolite M1 Valdecoxib metabolite M5 Oxidation - Methyl-Hydroxylation Unclear [6]
MR003487 Valdecoxib metabolite M1 Valdecoxib metabolite M3 Oxidation - Hydroxylation Unclear [5]
MR003489 Valdecoxib metabolite M1 Valdecoxib metabolite M4 Oxidation - Oxidation UGT [6], [5]
MR003495 Valdecoxib metabolite M1 Valdecoxib metabolite M1-G Conjugation - Glucuronidation UGT [6]
MR003481 Valdecoxib metabolite M2 Valdecoxib metabolite M5 Oxidation - Methyl-Hydroxylation Unclear [6]
MR003483 Valdecoxib metabolite M2 Valdecoxib metabolite M7 Unclear Unclear [5]
MR003494 Valdecoxib metabolite M2 Valdecoxib metabolite M2-G Conjugation - Glucuronidation UGT [5], [6]
MR003492 Valdecoxib metabolite M9 Valdecoxib metabolite M3 Unclear Unclear [5]
MR003493 Valdecoxib metabolite M9 Valdecoxib metabolite M9-G Unclear Unclear [5], [6]
MR014140 Valdecoxib metabolite M3 Valdecoxib metabolite M3-G Oxidation - S-Oxidation Unclear [5]
MR003490 Valdecoxib metabolite M4 Valdecoxib metabolite M6 Unclear Unclear [5]
MR003482 Valdecoxib metabolite M5 Valdecoxib metabolite M5-G Conjugation - Glucuronidation UGT [6]
MR003484 Valdecoxib metabolite M7 Valdecoxib metabolite M8 Oxidation - S-Oxidation Unclear [5]
⏷ Show the Full List of 18 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]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 ClinicalTrials.gov (NCT02729935) Parecoxib for Treatment of Catheter Related Bladder Discomfort.
2 Effects of Dexmedetomidine on the Pharmacokinetics of Parecoxib and Its Metabolite Valdecoxib in Beagles by UPLC-MS/MS. Biomed Res Int. 2020 Aug 6;2020:1563874. doi: 10.1155/2020/1563874.
3 Simultaneous determination of parecoxib and its main metabolites valdecoxib and hydroxylated valdecoxib in mouse plasma with a sensitive LC-MS/MS method to elucidate the decreased drug metabolism of tumor bearing mice. J Pharm Biomed Anal. 2018 Sep 5;158:1-7.
4 Comparison of pharmacokinetic profiles in hypoalbuminemia and healthy rats after parecoxib sodium injection?by LC-MS/MS. Bioanalysis. 2023 Feb;15(4):231-243. doi: 10.4155/bio-2022-0197.
5 Disposition of a specific cyclooxygenase-2 inhibitor, valdecoxib, in human Drug Metab Dispos. 2002 Sep;30(9):1013-21. doi: 10.1124/dmd.30.9.1013.
6 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.

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