Lumiracoxib (CHEM020245)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:57:09 UTC
Update Date2016-11-09 01:16:09 UTC
Accession NumberCHEM020245
Identification
Common NameLumiracoxib
ClassSmall Molecule
DescriptionLumiracoxib is a COX-2 selective non-steroidal anti-inflammatory drug (NSAID). On August 11, 2007, Australia's Therapeutic Goods Administration (TGA, the Australian equivalent of the FDA) cancelled the registration of lumiracoxib in Australia due to concerns that it may cause liver failure. New Zealand and Canada have also followed suit in recalling the drug.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-((2-Chloro-6-fluorophenyl)amino)-5-methylbenzeneacetic acidChEBI
COX 189ChEBI
COX-189ChEBI
COX189ChEBI
LumiracoxibumChEBI
PrexigeChEBI
2-((2-Chloro-6-fluorophenyl)amino)-5-methylbenzeneacetateGenerator
Chemical FormulaC15H13ClFNO2
Average Molecular Mass293.721 g/mol
Monoisotopic Mass293.062 g/mol
CAS Registry Number220991-20-8
IUPAC Name2-{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetic acid
Traditional Namelumiracoxib
SMILESCC1=CC=C(NC2=C(Cl)C=CC=C2F)C(CC(O)=O)=C1
InChI IdentifierInChI=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)
InChI KeyKHPKQFYUPIUARC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and one amino group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassToluenes
Direct ParentAminotoluenes
Alternative Parents
Substituents
  • Aminotoluene
  • Aniline or substituted anilines
  • Chlorobenzene
  • Fluorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl fluoride
  • Aryl halide
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Secondary amine
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Organohalogen compound
  • Organochloride
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0055 g/LALOGPS
logP4.56ALOGPS
logP4.31ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.11ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity75.91 m³·mol⁻¹ChemAxon
Polarizability28.53 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-2290000000-3dc98edbc540838a7548Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00g1-9152000000-5997fd55576c52d1c4b4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0090000000-df6ae4f2e3e5251bab0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-4e4dbea4d96e0566d989Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-2190000000-a2a86d3a4122bc5a8756Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0090000000-e36154890c850cdb9918Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-0090000000-554e0c5cc5da60a0d0b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05cv-3390000000-1fff2d7114e1511e7bb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0059-0090000000-15adaa3f8cb7a5dad42cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0090000000-954aa7c9b32169c17166Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5a-0970000000-6662a5b1b7750d52f2c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-57cb6b0c2531295b071dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00e9-2090000000-6ff6b3cb100db6c9f325Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9050000000-93dedc8134cc64db3e8dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01283
HMDB IDHMDB0015403
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLumiracoxib
Chemspider ID133236
ChEBI ID73044
PubChem Compound ID151166
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14965322
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15311562
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15456339
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17380211
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19800190
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21688392
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22069133
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22142375
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22621454
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22732767