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

General Information of Drug (ID: DR1666)
Drug Name
Valdecoxib
Synonyms
Valdecoxib; Valdyn; YM-974; Bextra; LNPDTQAFDNKSHK-UHFFFAOYSA-N; SC 65872; SC-65872; 181695-72-7; 4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide; 4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide; 4-(5-methyl-3-phenyl-4-isoxazolyl) benzenesulfonamide; 4-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonamide; Benzenesulfonamide, 4-(5-methyl-3-phenyl-4-isoxazolyl)-; CHEBI:63634; CHEMBL865; COX; HSDB 7302; Kudeq; MFCD00950568; NCGC00095129-01; UNII-2919279Q3W; p-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide
Indication Osteoarthritis [ICD11: FA00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 314.4 Topological Polar Surface Area 94.6
Heavy Atom Count 22 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
119607
PubChem SID
587378 ; 841634 ; 7300492 ; 7979620 ; 10238560 ; 11364641 ; 11367203 ; 11369765 ; 11372040 ; 11374755 ; 11377927 ; 11484171 ; 11488324 ; 11490816 ; 11492943 ; 11495561 ; 11528781 ; 11538199 ; 12015079 ; 14850214 ; 17137106 ; 17396876 ; 26612701 ; 26680171 ; 26719834 ; 26748964 ; 26748965 ; 29300443 ; 46386621 ; 46393843 ; 46506229 ; 46513481 ; 47885663 ; 48110737 ; 49665731 ; 49666068 ; 49681792 ; 50107497 ; 53789038 ; 57339580 ; 57578333 ; 58107175 ; 75154431 ; 85789263 ; 88531863 ; 92124765 ; 92308537 ; 92714410 ; 99444047 ; 103225393
ChEBI ID
CHEBI:63634
CAS Number
181695-72-7
TTD Drug ID
D0L6DA
Formula
C16H14N2O3S
Canonical SMILES
CC1=C(C(=NO1)C2=CC=CC=C2)C3=CC=C(C=C3)S(=O)(=O)N
InChI
1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20)16(18-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H2,17,19,20)
InChIKey
LNPDTQAFDNKSHK-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 metabolite M1 DM002428
9818888
Oxidation - Methyl-Hydroxylation 1 [5] , [4]
Valdecoxib metabolite M2 DM002423
11198846
Oxidation - N-Oxidation 1 [5] , [4]
Valdecoxib metabolite M9 DM002433
72710738
Oxidation - Hydroxylation 1 [5]
Valdecoxib N-glucuronide DM002738
145721920
Unclear 1 [5] , [4]
Valdecoxib metabolite M1-G DM002435
156028109
Unclear 2 [4]
Valdecoxib metabolite M2-G DM002434
156028043
Unclear 2 [4]
Valdecoxib metabolite M3 DM002429 N. A. Unclear 2 [5]
Valdecoxib metabolite M3 DM002429 N. A. Oxidation - Hydroxylation 2 [5]
Valdecoxib metabolite M4 DM002431
19608686
Oxidation - Oxidation 2 [4]
Valdecoxib metabolite M5 DM002424
156028093
Oxidation - Methyl-Hydroxylation 2 [4]
Valdecoxib metabolite M7 DM002426
17831363
Unclear 2 [5]
Valdecoxib metabolite M9-G DM002436 N. A. Unclear 2 [5]
Valdecoxib metabolite M3-G DM002430
156028032
Oxidation - S-Oxidation 3 [5]
Valdecoxib metabolite M5-G DM002425
155928966
Conjugation - Glucuronidation 3 [4]
Valdecoxib metabolite M6 DM002432
86212053
Unclear 3 [5]
Valdecoxib metabolite M8 DM002427
11565904
Oxidation - S-Oxidation 3 [5]
⏷ Show the Full List of 16  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003301 Valdecoxib Valdecoxib metabolite M2 Oxidation - N-Oxidation Unclear [5], [4]
MR003302 Valdecoxib Valdecoxib metabolite M1 Oxidation - Methyl-Hydroxylation CYP2C9 ... [5], [4]
MR003303 Valdecoxib Valdecoxib metabolite M9 Oxidation - Hydroxylation Unclear [5]
MR003304 Valdecoxib Valdecoxib N-glucuronide Unclear UGT [5], [4]
MR003293 Valdecoxib metabolite M1 Valdecoxib metabolite M5 Oxidation - Methyl-Hydroxylation Unclear [4]
MR003294 Valdecoxib metabolite M1 Valdecoxib metabolite M3 Oxidation - Hydroxylation Unclear [5]
MR003295 Valdecoxib metabolite M1 Valdecoxib metabolite M4 Oxidation - Oxidation UGT [4]
MR003296 Valdecoxib metabolite M1 Valdecoxib metabolite M1-G Unclear UGT [4]
MR003288 Valdecoxib metabolite M2 Valdecoxib metabolite M5 Oxidation - Methyl-Hydroxylation Unclear [4]
MR003289 Valdecoxib metabolite M2 Valdecoxib metabolite M7 Unclear Unclear [5]
MR003290 Valdecoxib metabolite M2 Valdecoxib metabolite M2-G Unclear UGT [4]
MR003299 Valdecoxib metabolite M9 Valdecoxib metabolite M3 Unclear Unclear [5]
MR003300 Valdecoxib metabolite M9 Valdecoxib metabolite M9-G Unclear CYP2C9 ... [5]
MR003297 Valdecoxib metabolite M3 Valdecoxib metabolite M3-G Oxidation - S-Oxidation Unclear [5]
MR003298 Valdecoxib metabolite M4 Valdecoxib metabolite M6 Unclear Unclear [5]
MR003291 Valdecoxib metabolite M5 Valdecoxib metabolite M5-G Conjugation - Glucuronidation Unclear [4]
MR003292 Valdecoxib metabolite M7 Valdecoxib metabolite M8 Oxidation - S-Oxidation Unclear [5]
⏷ Show the Full List of 17 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
[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[4]
References
1 Valdecoxib was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Genetically based impairment in CYP2C8- and CYP2C9-dependent NSAID metabolism as a risk factor for gastrointestinal bleeding: is a combination of pharmacogenomics and metabolomics required to improve personalized medicine? Expert Opin Drug Metab Toxicol. 2009 Jun;5(6):607-20.
3 Simultaneous assessment of drug interactions with low- and high-extraction opioids: application to parecoxib effects on the pharmacokinetics and pharmacodynamics of fentanyl and alfentanil. Anesthesiology. 2003 Apr;98(4):853-61.
4 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.
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.

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