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

General Information of Drug (ID: DR0993)
Drug Name
Lumiracoxib
Synonyms
Lumaricoxib; Lumiracoxib; Prexige; COX 189; COX-189; COX189; Joicela; V91T9204HU; 2-((2-Chloro-6-fluorophenyl)amino)-5-methylbenzeneacetic acid; 2-((2-Chloro-6-fluorophenyl)amino)-5-methylphenyl)acetic acid; 2-(2-(2-chloro-6-fluorophenylamino)-5-methylphenyl)aceticacid; 2-[2-(2-chloro-6-fluoroanilino)-5-methylphenyl]acetic acid; 220991-20-8; CHEBI:73044; CHEMBL404108; DSSTox_CID_28961; DSSTox_GSID_49035; DSSTox_RID_83226; NCGC00181795-01; UNII-V91T9204HU; {2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetic acid
Indication Anaesthesia [ICD11: 8E22] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 293.72 Topological Polar Surface Area 49.3
Heavy Atom Count 20 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
151166
PubChem SID
6889610 ; 10251040 ; 12015303 ; 14898109 ; 17397805 ; 46227733 ; 46506378 ; 50069519 ; 50070561 ; 50071183 ; 50126342 ; 50146068 ; 57347306 ; 76715547 ; 81041141 ; 81145916 ; 92718829 ; 103562109 ; 104084914 ; 104430341 ; 121362203 ; 123043886 ; 125345177 ; 126628436 ; 126645712 ; 126669886 ; 128383506 ; 131305772 ; 134338241 ; 135106949 ; 136948146 ; 137001909 ; 139667196 ; 144162368 ; 144207115 ; 152034557 ; 160661707 ; 160661708 ; 160964604 ; 162009833 ; 162169214 ; 163108814 ; 164786748 ; 166237623 ; 170465597 ; 172659601 ; 175610946 ; 178100246 ; 179150172 ; 184545760
ChEBI ID
CHEBI:73044
CAS Number
220991-20-8
TTD Drug ID
D04YMH
Formula
C15H13ClFNO2
Canonical SMILES
CC1=CC(=C(C=C1)NC2=C(C=CC=C2Cl)F)CC(=O)O
InChI
1S/C15H13ClFNO2/c1-9-5-6-13(10(7-9)8-14(19)20)18-15-11(16)3-2-4-12(15)17/h2-7,18H,8H2,1H3,(H,19,20)
InChIKey
KHPKQFYUPIUARC-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
Lumiracoxib metabolite M21 DM002609
154585067
Oxidation - Methyl-Hydroxylation 1 [3]
Lumiracoxib metabolite M23 DM002617
9904747
Oxidation - Hydroxylation 1 [3]
Lumiracoxib metabolite M24 DM002626
154585084
Conjugation - Glucuronidation 1 [3]
Lumiracoxib metabolite M11 DM002610
85972641
Oxidation - Oxidation 2 [3]
Lumiracoxib metabolite M22 DM002625
154699950
Conjugation - Glucuronidation 2 [3]
Lumiracoxib metabolite M25 DM002623
154584834
Unclear 2 [3]
Lumiracoxib metabolite M9 DM002616
154584895
Unclear 2 [3]
Lumiracoxib metabolite M15 DM002615
154584901
Unclear 3 [3]
Lumiracoxib metabolite M20 DM002624
154584798
Conjugation - Glucuronidation 3 [3]
Lumiracoxib metabolite M3 DM002622 N. A. Conjugation - Glucuronidation 3 [3]
Lumiracoxib metabolite M5 DM002611
135390857
Oxidation - Hydroxylation 3 [3]
Lumiracoxib metabolite M5 DM002611
135390857
Unclear 3 [3]
Lumiracoxib metabolite M16/metabolite M17 DM002620 N. A. Conjugation - Glucuronidation 4 [3]
Lumiracoxib metabolite M2 DM002621
154584980
Other reaction - Sulfonation 4 [3]
Lumiracoxib metabolite M8 DM002612
154585079
Oxidation - Hydroxylation 4 [3]
Lumiracoxib metabolite M12 DM002613 N. A. Oxidation - Hydroxylation 5 [3]
Lumiracoxib metabolite M4/metabolite M6 DM002618 N. A. Unclear 5 [3]
Lumiracoxib metabolite M8 DM002612
154585079
Conjugation - Glucuronidation 5 [3]
Lumiracoxib metabolite M13 DM002614 N. A. Conjugation - Glucuronidation 6 [3]
⏷ Show the Full List of 19  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001602 Lumiracoxib Lumiracoxib metabolite M21 Oxidation - Methyl-Hydroxylation CYP2C19 ... [3]
MR001603 Lumiracoxib Lumiracoxib metabolite M23 Oxidation - Hydroxylation CYP2C19 ... [3]
MR001604 Lumiracoxib Lumiracoxib metabolite M24 Conjugation - Glucuronidation UGT1A1 [3]
MR001584 Lumiracoxib metabolite M21 Lumiracoxib metabolite M11 Oxidation - Oxidation Unclear [3]
MR001585 Lumiracoxib metabolite M21 Lumiracoxib metabolite M9 Unclear Unclear [3]
MR001598 Lumiracoxib metabolite M23 Lumiracoxib metabolite M9 Unclear Unclear [3]
MR001599 Lumiracoxib metabolite M23 Lumiracoxib metabolite M25 Unclear Unclear [3]
MR001600 Lumiracoxib metabolite M23 Lumiracoxib metabolite M22 Conjugation - Glucuronidation UGT1A1 [3]
MR001586 Lumiracoxib metabolite M11 Lumiracoxib metabolite M5 Oxidation - Hydroxylation SULT2A1 [3]
MR001587 Lumiracoxib metabolite M11 Lumiracoxib metabolite M15 Unclear Unclear [3]
MR001588 Lumiracoxib metabolite M11 Lumiracoxib metabolite M3 Conjugation - Glucuronidation UGT1A1 [3]
MR001601 Lumiracoxib metabolite M25 Lumiracoxib metabolite M20 Conjugation - Glucuronidation UGT1A1 [3]
MR014167 Lumiracoxib metabolite M9 Lumiracoxib metabolite M5 Oxidation - Hydroxylation Unclear [3]
MR001595 Lumiracoxib metabolite M15 Lumiracoxib metabolite M8 Oxidation - Hydroxylation Unclear [3]
MR001596 Lumiracoxib metabolite M15 Lumiracoxib metabolite M16/metabolite M17 Conjugation - Glucuronidation UGT1A1 [3]
MR001589 Lumiracoxib metabolite M5 Lumiracoxib metabolite M8 Oxidation - Hydroxylation Unclear [3]
MR001590 Lumiracoxib metabolite M5 Lumiracoxib metabolite M2 Other reaction - Sulfonation Unclear [3]
MR001591 Lumiracoxib metabolite M8 Lumiracoxib metabolite M12 Oxidation - Hydroxylation Unclear [3]
MR001592 Lumiracoxib metabolite M8 Lumiracoxib metabolite M4/metabolite M6 Unclear SULT2A1 [3]
MR001593 Lumiracoxib metabolite M8 Lumiracoxib metabolite M10 Conjugation - Glucuronidation UGT1A1 [3]
MR001594 Lumiracoxib metabolite M12 Lumiracoxib metabolite M13 Conjugation - Glucuronidation UGT1A1 [3]
⏷ Show the Full List of 21 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]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
References
1 ClinicalTrials.gov (NCT00348491) Efficacy of Lumiracoxib in Relieving Moderate to Severe Post-dental Surgery Pain, Compared to Both Placebo and Celecoxib.
2 Clinical pharmacology of lumiracoxib: a selective cyclo-oxygenase-2 inhibitor. Clin Pharmacokinet. 2005;44(12):1247-66.
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.

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