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

General Information of Drug (ID: DR0670)
Drug Name
Etoricoxib
Synonyms
Etoricoxib; Etoricoxib [USAN:INN:BAN]; Etoricoxibe; L-791456; L791456; MK 0663; MK 663; MK-0663; MK-663; MK0663; Arcoxia; Nucoxia; Tauxib; WRX4NFY03R; 202409-33-4; 5-Chloro-6'-methyl-3-(4-(methylsulfonyl)phenyl)-2,3'-bipyridine; 5-Chloro-6'-methyl-3-(p-(methylsulfonyl)phenyl)-2,3'-bipyridine; 5-chloro-2-(6-methylpyridin-3-yl)-3-(4-methylsulfonylphenyl)pyridine; 5-chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-2,3'-bipyridine; AK115816; Algix; CHEBI:6339; CHEMBL416146; MNJVRJDLRVPLFE-UHFFFAOYSA-N; NCGC00164578-01; UNII-WRX4NFY03R
Indication Anaesthesia [ICD11: 8E22] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 358.8 Topological Polar Surface Area 68.3
Heavy Atom Count 24 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
123619
PubChem SID
13883 ; 6613371 ; 7979618 ; 10240801 ; 12015199 ; 14828179 ; 17397801 ; 26758000 ; 29303851 ; 46504505 ; 49655565 ; 50065687 ; 57340488 ; 58108264 ; 76715678 ; 79356674 ; 85209827 ; 92309001 ; 99214846 ; 99437360 ; 99443637 ; 103169851 ; 103853298 ; 103965754 ; 104418927 ; 118048491 ; 125536726 ; 126645211 ; 126671483 ; 128620771 ; 134338025 ; 135079337 ; 137001913 ; 142355996 ; 144205759 ; 160964864 ; 162188900 ; 163123240 ; 163414197 ; 163620860 ; 163686187 ; 163849037 ; 164787972 ; 170465621 ; 171579232 ; 175266728 ; 175611945 ; 176484244 ; 177749312 ; 178100245
ChEBI ID
CHEBI:6339
CAS Number
202409-33-4
TTD Drug ID
D09MGR
Formula
C18H15ClN2O2S
Canonical SMILES
CC1=NC=C(C=C1)C2=C(C=C(C=N2)Cl)C3=CC=C(C=C3)S(=O)(=O)C
InChI
1S/C18H15ClN2O2S/c1-12-3-4-14(10-20-12)18-17(9-15(19)11-21-18)13-5-7-16(8-6-13)24(2,22)23/h3-11H,1-2H3
InChIKey
MNJVRJDLRVPLFE-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
6-Hydroxymethyletoricoxib DM006657
44266438
Other reaction - 6-methylhydroxylation 1 [3]
Etoricoxib 1'-N'-oxide DM006655
44266508
Oxidation - 1-N-oxidation 1 [3]
6-Carboxy-etoricoxib DM006658
44266451
Oxidation - Oxidationn 2 [3]
6-Hydroxymethyletoricoxib glucuronide DM006659 N. A. Conjugation - Glucuronidation 2 [3]
6-Hydroxymethyletoricoxib-1'-N'-oxide DM006656 N. A. Oxidation - 1-N-oxidation 2 [3]
6-Hydroxymethyletoricoxib-1'-N'-oxide DM006656 N. A. Other reaction - 6-methylhydroxylation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007163 Etoricoxib Etoricoxib 1'-N'-oxide Oxidation - 1-N-oxidation CYP3A4 ... [3]
MR007165 Etoricoxib 6-Hydroxymethyletoricoxib Other reaction - 6-methylhydroxylation CYP3A4 ... [3]
MR007166 6-Hydroxymethyletoricoxib 6-Carboxy-etoricoxib Oxidation - Oxidationn CYP3A4 ... [3]
MR007167 6-Hydroxymethyletoricoxib 6-Hydroxymethyletoricoxib glucuronide Conjugation - Glucuronidation UGT [3]
MR007168 6-Hydroxymethyletoricoxib 6-Hydroxymethyletoricoxib-1'-N'-oxide Oxidation - 1-N-oxidation CYP3A4 ... [3]
MR007164 Etoricoxib 1'-N'-oxide 6-Hydroxymethyletoricoxib-1'-N'-oxide Other reaction - 6-methylhydroxylation CYP3A4 ... [4]
⏷ 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 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_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 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 ClinicalTrials.gov (NCT00757627) Patient-Reported Effectiveness and Safety of Etoricoxib in Osteoarthritis (OA)(0663-113).
2 Role of human liver cytochrome P4503A in the metabolism of etoricoxib, a novel cyclooxygenase-2 selective inhibitor. Drug Metab Dispos. 2001 Jun;29(6):813-20.
3 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.
4 Absorption, metabolism, and excretion of etoricoxib, a potent and selective cyclooxygenase-2 inhibitor, in healthy male volunteers

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