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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL404108
CHEMBL404108
Compound Name LUMIRACOXIB
ChEMBL Synonyms PREXIGE | LUMIRACOXIB | COX-189
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names PREXIGE
Molecular Formula C15H13ClFNO2

Additional synonyms for CHEMBL404108 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Cc1ccc(Nc2c(F)cccc2Cl)c(CC(=O)O)c1
Standard InChI InChI=1S/C15H13ClFNO2/c1-9-5-6-13(10(7-9)8-14(19)20)18-15-11 ...
Download InChI
Standard InChI Key KHPKQFYUPIUARC-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL404108

Molecule Features

CHEMBL404108 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 2007
Country European Union
Reason Liver injury
Class Hepatotoxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Cyclooxygenase-2 inhibitor Cyclooxygenase-2 PubMed PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Arthritis, RheumatoidD001172EFO:0000685rheumatoid arthritis3ClinicalTrials
Osteoarthritis, HipD015207EFO:1000786osteoarthritis, hip3ClinicalTrials
Rheumatic DiseasesD012216EFO:0005755rheumatic disease4ATC
OsteoarthritisD010003EFO:0002506osteoarthritis3ClinicalTrials

Clinical Data

ClinicalTrials.gov LUMIRACOXIB
The Cochrane Collaboration LUMIRACOXIB

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL404108. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL4321 Cyclooxygenase-2 Mus musculus 0.999
CHEMBL5658 Prostaglandin E synthase Homo sapiens 0.973
CHEMBL2949 Cyclooxygenase-1 Ovis aries 0.911
CHEMBL5071 G protein-coupled receptor 44 Homo sapiens 0.462
CHEMBL1947 Thyroid hormone receptor beta-1 Homo sapiens 0.342
CHEMBL3587 Dual specificity mitogen-activated protein kinase kinase 1 Homo sapiens 0.272
CHEMBL221 Cyclooxygenase-1 Homo sapiens 0.266
CHEMBL2568 Liver glycogen phosphorylase Homo sapiens 0.210



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4321 Cyclooxygenase-2 Mus musculus 0.999
CHEMBL5658 Prostaglandin E synthase Homo sapiens 0.920
CHEMBL5071 G protein-coupled receptor 44 Homo sapiens 0.278

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
293.7 293.0619 4.16 4 49.33 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 2 0 3 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.18 - 4.74 1.66 2 20 0.89

Structural Alerts

There are no structural alerts for CHEMBL404108

Compound Cross References

ATC M - MUSCULO-SKELETAL SYSTEM
M01 - ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M01A - ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
M01AH - Coxibs
M01AH06 - lumiracoxib

ChemSpider ChemSpider:KHPKQFYUPIUARC-UHFFFAOYSA-N
PubChem SID: 144207115 SID: 170465597
Wikipedia Lumiracoxib

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL404108



ACToR 220991-20-8
BindingDB 50207446
Brenda 143397
ChEBI 73044
DrugBank DB01283
DrugCentral 1618
eMolecules 8296333
EPA CompTox Dashboard DTXSID9049035
FDA SRS V91T9204HU
Guide to Pharmacology 2897
Human Metabolome Database HMDB0015403
IBM Patent System 82DD486B05C723C829542ED58B9530A6
Mcule MCULE-3735047846
MolPort MolPort-003-824-911
Nikkaji J1.996.164H
PDBe LUR
PharmGKB PA164769031
PubChem 151166
PubChem: Drugs of the Future 12015303
PubChem: Thomson Pharma 14898109
Selleck lumiracoxib-cox-189
SureChEMBL SCHEMBL4479
ZINC ZINC000000007563

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/KHPKQFYUPIUARC-UHFFFAOYSA-N spacer
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