Details of the Drug

General Information of Drug (ID: DM1S4AG)

Drug Name
Lumiracoxib
Synonyms
Joicela; Prexige; Novartis brand of lumiracoxib; COX 189; COX189; COX-189; Lumiracoxib [USAN:INN]; Prexige (Novartis); Prexige (TN); Lumiracoxib (USAN/INN); 2-((2-Chloro-6-fluorophenyl)amino)-5-methylbenzeneacetic acid; 2-((2-Chloro-6-fluorophenyl)amino)-5-methylphenyl)acetic acid; 2-(2-((2-chloro-6-fluoro-phenyl)amino)-5-methyl-phenyl)acetic acid; 2-[2-(2-chloro-6-fluoroanilino)-5-methylphenyl]acetic acid
Indication
Disease Entry ICD 11 Status REF
Chronic renal failure GB61.Z Approved [1]
Knee osteoarthritis FA01 Approved [2]
Osteoarthritis FA00-FA05 Approved [3]
Therapeutic Class
Antiinflammatory Agents
Affected Organisms
Humans and other mammals
ATC Code
M01AH06: Lumiracoxib
M01AH: Coxibs
M01A: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
M01: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M: MUSCULO-SKELETAL SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 293.72
Logarithm of the Partition Coefficient (xlogp) 4.2
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Bioavailability
74% of drug becomes completely available to its intended biological destination(s) [5]
Half-life
The concentration or amount of drug in body reduced by one-half in 4 hours [6]
Metabolism
The drug is metabolized via the hepatic []
Chemical Identifiers
Formula
C15H13ClFNO2
IUPAC Name
2-[2-(2-chloro-6-fluoroanilino)-5-methylphenyl]acetic acid
Canonical SMILES
CC1=CC(=C(C=C1)NC2=C(C=CC=C2Cl)F)CC(=O)O
InChI
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
Cross-matching ID
PubChem CID
151166
ChEBI ID
CHEMBL404108
CAS Number
220991-20-8
UNII
V91T9204HU
DrugBank ID
DB01283
TTD ID
D04YMH
VARIDT ID
DR01172
INTEDE ID
DR0993
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin G/H synthase 2 (COX-2) TTVKILB PGH2_HUMAN Inhibitor [7]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [8]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [8]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [8]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DE85D2P UD19_HUMAN Substrate [9]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Antileukoproteinase (SLPI) OTUNFUU8 SLPI_HUMAN Gene/Protein Processing [10]
Hepatocyte growth factor receptor (MET) OT7K55MU MET_HUMAN Gene/Protein Processing [10]
HLA class II histocompatibility antigen, DQ alpha 1 chain (HLA-DQA1) OTC6GISG DQA1_HUMAN Drug Response [11]
HLA class II histocompatibility antigen, DQ beta 1 chain (HLA-DQB1) OTVVI3UI DQB1_HUMAN Drug Response [11]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [10]
Proepiregulin (EREG) OTRM4NQY EREG_HUMAN Gene/Protein Processing [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Chronic renal failure
ICD Disease Classification GB61.Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostaglandin G/H synthase 2 (COX-2) DTT PTGS2 2.03E-07 1.68 3.86
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 2.43E-01 9.13E-02 3.60E-01
Mephenytoin 4-hydroxylase (CYP2C19) DME CYP2C19 5.51E-02 1.95E-01 1.20E+00
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 3.04E-01 -5.14E-02 -1.57E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Adverse effects of cyclooxygenase 2 inhibitors on renal and arrhythmia events: meta-analysis of randomized trials. JAMA. 2006 Oct 4;296(13):1619-32.
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2897).
3 Lumiracoxib in the management of osteoarthritis and acute pain. Expert Opin Pharmacother. 2007 Jul;8(10):1551-64.
4 BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
5 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
6 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7 Dissociation of airway inflammation and hyperresponsiveness by cyclooxygenase inhibition in allergen challenged mice. Eur Respir J. 2009 Jul;34(1):200-8.
8 Clinical pharmacology of lumiracoxib: a selective cyclo-oxygenase-2 inhibitor. Clin Pharmacokinet. 2005;44(12):1247-66.
9 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.
10 An in vitro coculture system of human peripheral blood mononuclear cells with hepatocellular carcinoma-derived cells for predicting drug-induced liver injury. Arch Toxicol. 2021 Jan;95(1):149-168. doi: 10.1007/s00204-020-02882-4. Epub 2020 Aug 20.
11 A genome-wide study identifies HLA alleles associated with lumiracoxib-related liver injury. Nat Genet. 2010 Aug;42(8):711-4. doi: 10.1038/ng.632. Epub 2010 Jul 18.