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Compound Detail

CHEMBL404108

LUMIRACOXIB
💊 Approved Drug
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💊 Approved Drug
Cc1ccc(Nc2c(F)cccc2Cl)c(CC(=O)O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL404108
Name LUMIRACOXIB
Phase Approved
Structure Type MOL
InChI Key KHPKQFYUPIUARC-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

COX-189 Lumiracoxib Prexige
4
Targets
11
Activities
2
Assay Types
0
PK Parameters
20
Publications
3
Known Names
5
Indications
1
Mechanisms

Molecular Properties

293.7
MW (Da)
4.16
ALogP
2
HBA
2
HBD
49.3
PSA (Ų)
0.89
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2005
Availability Withdrawn
Chirality Achiral

Routes of Administration

Oral

Flags

Withdrawn
USAN Stem -coxib
USAN Year 2002

Extended Properties

Molecular Formula C15H13ClFNO2
MW 293.73
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -1.39

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cyclooxygenase-2 inhibitor INHIBITOR Prostaglandin G/H synthase 2 ✓ ✓

Indications

Rheumatic Diseases Arthritis, Rheumatoid Osteoarthritis Osteoarthritis, Hip Osteoarthritis, Knee

ATC Classification

M01AH06
lumiracoxib
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

Drug Warnings

Withdrawn
hepatotoxicity
Liver injury
Country: Canada; Australia; European Union   Year: 2007
Withdrawn
hepatotoxicity
Serious liver-related adverse events
Country: Canada; Australia; European Union   Year: 2007
Withdrawn
hepatotoxicity
serious liver side effects
Country: Canada; Australia; European Union   Year: 2007
Withdrawn
hepatotoxicity
Liver injury
Country: Canada; Australia; European Union   Year: 2007
Withdrawn
hepatotoxicity
Serious liver-related adverse events
Country: Canada; Australia; European Union   Year: 2007
Withdrawn
hepatotoxicity
serious liver side effects
Country: Canada; Australia; European Union   Year: 2007

Activity Summary

IC50 9 meas. best 8.15
Ki 2 meas. best 6.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 8.15 8.15 7.0 1
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 8.15 7.155 7.0 6
Prostaglandin G/H synthase 2
CHEMBL4321
 IC50 7.4 7.4 40.0 1
Unchecked
CHEMBL612545
 IC50 6.94 6.94 114.0 1
Prostaglandin G/H synthase 2
CHEMBL230
 Ki 6.5 6.5 320.0 1
Unchecked
CHEMBL612545
 Ki 6.12 6.12 750.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 2 IC50 = 7.0 nM 8.15 Inhibition of COX2 17341061
Prostaglandin G/H synthase 1 IC50 = 7.0 nM 8.15 Inhibition of COX1 22236250
Prostaglandin G/H synthase 2 IC50 = 40.0 nM 7.4 Inhibition of purified mouse COX-2 assessed as inhibition of PGE2-G/PGD2-G forma... 24060487
Prostaglandin G/H synthase 2 IC50 = 60.0 nM 7.22 Inhibition of COX-2 (unknown origin) 26898334
Prostaglandin G/H synthase 2 IC50 = 107.0 nM 6.97 Inhibition of human COX2 for 17 mins pre-incubated before addition of [1-14C]ara... 17434872
Unchecked IC50 = 114.0 nM 6.94 Inhibition of mouse COX2 V349I mutant 20 mins preincubated before addition of [1... 17434872
Prostaglandin G/H synthase 2 IC50 = 130.0 nM 6.89 Inhibition of human COX2 mediated PGE2 production in IL-1-beta-induced human der... 17434872
Prostaglandin G/H synthase 2 IC50 = 140.0 nM 6.85 Inhibition of human COX2 mediated PGE2 production in human whole blood 17434872
Prostaglandin G/H synthase 2 IC50 = 140.0 nM 6.85 Inhibition of COX2 (unknown origin) -
Prostaglandin G/H synthase 2 Ki = 320.0 nM 6.5 Inhibition of human COX2 preincubated before addition of [1-14C]arachidonic acid 17434872
Unchecked Ki = 750.0 nM 6.12 Inhibition of mouse COX2 V349I mutant pre-incubated before addition of [1-14C]ar... 17434872

Literature References

PubMed DOI Target Context # Activities
17434872 10.1074/jbc.m609883200 Prostaglandin G/H synthase 2 14
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
17434872 10.1074/jbc.m609883200 Unchecked 5
37468498 10.1038/s41467-023-40064-9 Bile acid receptor 4
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
24060487 10.1016/j.bmcl.2013.08.097 Prostaglandin G/H synthase 2 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Glucocorticoid receptor 2
37468498 10.1038/s41467-023-40064-9 Peroxisome proliferator-activated receptor alpha 2
37468498 10.1038/s41467-023-40064-9 Retinoic acid receptor alpha 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 2
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 2
37468498 10.1038/s41467-023-40064-9 Oxysterols receptor LXR-alpha 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Peroxisome proliferator-activated receptor gamma 2
37468498 10.1038/s41467-023-40064-9 Oxysterols receptor LXR-beta 2
17434872 10.1074/jbc.m609883200 Prostaglandin G/H synthase 1 2

Data from ChEMBL 36 via Core Engine