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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:58 UTC
HMDB IDHMDB0015403
Secondary Accession Numbers
  • HMDB15403
Metabolite Identification
Common NameLumiracoxib
DescriptionLumiracoxib, also known as COX 189 or prexige, 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. Lumiracoxib is a drug which is used for the acute and chronic treatment of the signs and symptoms of osteoarthritis of the knee in adults. Lumiracoxib is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, lumiracoxib is involved in lumiracoxib action pathway.
Structure
Data?1582753293
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 Weight293.721
Monoisotopic Molecular Weight293.061884577
IUPAC Name2-{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetic acid
Traditional Namelumiracoxib
CAS Registry Number220991-20-8
SMILES
CC1=CC=C(NC2=C(Cl)C=CC=C2F)C(CC(O)=O)=C1
InChI Identifier
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)
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
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0055 g/LNot Available
LogP3.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+167.65130932474
DeepCCS[M-H]-165.29330932474
DeepCCS[M-2H]-198.17930932474
DeepCCS[M+Na]+173.74430932474
AllCCS[M+H]+162.632859911
AllCCS[M+H-H2O]+159.132859911
AllCCS[M+NH4]+165.932859911
AllCCS[M+Na]+166.932859911
AllCCS[M-H]-160.632859911
AllCCS[M+Na-2H]-159.832859911
AllCCS[M+HCOO]-159.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LumiracoxibCC1=CC=C(NC2=C(Cl)C=CC=C2F)C(CC(O)=O)=C13907.3Standard polar33892256
LumiracoxibCC1=CC=C(NC2=C(Cl)C=CC=C2F)C(CC(O)=O)=C12324.9Standard non polar33892256
LumiracoxibCC1=CC=C(NC2=C(Cl)C=CC=C2F)C(CC(O)=O)=C12317.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lumiracoxib,1TMS,isomer #1CC1=CC=C(NC2=C(F)C=CC=C2Cl)C(CC(=O)O[Si](C)(C)C)=C12266.5Semi standard non polar33892256
Lumiracoxib,1TMS,isomer #2CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C)C(CC(=O)O)=C12276.7Semi standard non polar33892256
Lumiracoxib,2TMS,isomer #1CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C12253.8Semi standard non polar33892256
Lumiracoxib,2TMS,isomer #1CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C12227.9Standard non polar33892256
Lumiracoxib,2TMS,isomer #1CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C12624.5Standard polar33892256
Lumiracoxib,1TBDMS,isomer #1CC1=CC=C(NC2=C(F)C=CC=C2Cl)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C12518.4Semi standard non polar33892256
Lumiracoxib,1TBDMS,isomer #2CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C(C)(C)C)C(CC(=O)O)=C12509.2Semi standard non polar33892256
Lumiracoxib,2TBDMS,isomer #1CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C12733.6Semi standard non polar33892256
Lumiracoxib,2TBDMS,isomer #1CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C12629.8Standard non polar33892256
Lumiracoxib,2TBDMS,isomer #1CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C12848.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lumiracoxib GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-2290000000-3dc98edbc540838a75482017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lumiracoxib GC-MS (1 TMS) - 70eV, Positivesplash10-00g1-9152000000-5997fd55576c52d1c4b42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lumiracoxib GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumiracoxib 10V, Positive-QTOFsplash10-002f-0090000000-df6ae4f2e3e5251bab0d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumiracoxib 20V, Positive-QTOFsplash10-0002-0090000000-4e4dbea4d96e0566d9892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumiracoxib 40V, Positive-QTOFsplash10-001j-2190000000-a2a86d3a4122bc5a87562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumiracoxib 10V, Negative-QTOFsplash10-0007-0090000000-e36154890c850cdb99182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumiracoxib 20V, Negative-QTOFsplash10-0007-0090000000-554e0c5cc5da60a0d0b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumiracoxib 40V, Negative-QTOFsplash10-05cv-3390000000-1fff2d7114e1511e7bb02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumiracoxib 10V, Positive-QTOFsplash10-0059-0090000000-15adaa3f8cb7a5dad42c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumiracoxib 20V, Positive-QTOFsplash10-000t-0090000000-954aa7c9b32169c171662021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumiracoxib 40V, Positive-QTOFsplash10-0a5a-0970000000-6662a5b1b7750d52f2c02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumiracoxib 10V, Negative-QTOFsplash10-0006-0090000000-57cb6b0c2531295b071d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumiracoxib 20V, Negative-QTOFsplash10-00e9-2090000000-6ff6b3cb100db6c9f3252021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumiracoxib 40V, Negative-QTOFsplash10-001i-9050000000-93dedc8134cc64db3e8d2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01283 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01283 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01283
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID133236
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLumiracoxib
METLIN IDNot Available
PubChem Compound151166
PDB IDNot Available
ChEBI ID73044
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. [PubMed:19515014 ]
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Capone ML, Tacconelli S, Sciulli MG, Patrignani P: Clinical pharmacology of selective COX-2 inhibitors. Int J Immunopathol Pharmacol. 2003 May-Aug;16(2 Suppl):49-58. [PubMed:14552704 ]
  2. Tacconelli S, Capone ML, Patrignani P: Clinical pharmacology of novel selective COX-2 inhibitors. Curr Pharm Des. 2004;10(6):589-601. [PubMed:14965322 ]
  3. Atherton C, Jones J, McKaig B, Bebb J, Cunliffe R, Burdsall J, Brough J, Stevenson D, Bonner J, Rordorf C, Scott G, Branson J, Hawkey CJ: Pharmacology and gastrointestinal safety of lumiracoxib, a novel cyclooxygenase-2 selective inhibitor: An integrated study. Clin Gastroenterol Hepatol. 2004 Feb;2(2):113-20. [PubMed:15017615 ]
  4. Kalbag J, Yeh CM, Milosavljev S, Lasseter K, Oberstein S, Rordorf C: No influence of moderate hepatic impairment on the pharmacokinetics of lumiracoxib, an oral COX-2 selective inhibitor. Pharmacol Res. 2004 Aug;50(2):181-6. [PubMed:15177307 ]
  5. Esser R, Berry C, Du Z, Dawson J, Fox A, Fujimoto RA, Haston W, Kimble EF, Koehler J, Peppard J, Quadros E, Quintavalla J, Toscano K, Urban L, van Duzer J, Zhang X, Zhou S, Marshall PJ: Preclinical pharmacology of lumiracoxib: a novel selective inhibitor of cyclooxygenase-2. Br J Pharmacol. 2005 Feb;144(4):538-50. [PubMed:15655513 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Capone ML, Tacconelli S, Sciulli MG, Patrignani P: Clinical pharmacology of selective COX-2 inhibitors. Int J Immunopathol Pharmacol. 2003 May-Aug;16(2 Suppl):49-58. [PubMed:14552704 ]
  2. Esser R, Berry C, Du Z, Dawson J, Fox A, Fujimoto RA, Haston W, Kimble EF, Koehler J, Peppard J, Quadros E, Quintavalla J, Toscano K, Urban L, van Duzer J, Zhang X, Zhou S, Marshall PJ: Preclinical pharmacology of lumiracoxib: a novel selective inhibitor of cyclooxygenase-2. Br J Pharmacol. 2005 Feb;144(4):538-50. [PubMed:15655513 ]
  3. Jermany J, Branson J, Schmouder R, Guillaume M, Rordorf C: Lumiracoxib does not affect the ex vivo antiplatelet aggregation activity of low-dose aspirin in healthy subjects. J Clin Pharmacol. 2005 Oct;45(10):1172-8. [PubMed:16172182 ]
  4. Warner TD, Vojnovic I, Bishop-Bailey D, Mitchell JA: Influence of plasma protein on the potencies of inhibitors of cyclooxygenase-1 and -2. FASEB J. 2006 Mar;20(3):542-4. Epub 2006 Jan 10. [PubMed:16403783 ]
  5. Blobaum AL, Marnett LJ: Molecular determinants for the selective inhibition of cyclooxygenase-2 by lumiracoxib. J Biol Chem. 2007 Jun 1;282(22):16379-90. Epub 2007 Apr 12. [PubMed:17434872 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]