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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2019-01-11 19:36:03 UTC
HMDB IDHMDB0015565
Secondary Accession Numbers
  • HMDB15565
Metabolite Identification
Common NameEtoricoxib
DescriptionEtoricoxib is a new COX-2 selective inhibitor. Current therapeutic indications are: treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, chronic low back pain, acute pain and gout. Like any other COX-2 selective inhibitor, Etoricoxib selectively inhibits isoform 2 of cyclo-oxigenase enzyme (COX-2). This reduces the generation of prostaglandins (PGs) from arachidonic acid.
Structure
Data?1547235363
Synonyms
ValueSource
5-chloro-2-(6-Methylpyridin-3-yl)-3-(4-(methylsulfonyl)phenyl)pyridineChEBI
5-chloro-3-(4-Methanesulfonyl-phenyl)-6'-methyl-[2,3']bipyridinylChEBI
5-chloro-6'-Methyl-3-(P-(methylsulfonyl)phenyl)-2,3'-bipyridineChEBI
EtoricoxibumChEBI
L791456ChEBI
5-chloro-2-(6-Methylpyridin-3-yl)-3-(4-(methylsulphonyl)phenyl)pyridineGenerator
5-chloro-3-(4-Methanesulphonyl-phenyl)-6'-methyl-[2,3']bipyridinylGenerator
5-chloro-6'-Methyl-3-(P-(methylsulphonyl)phenyl)-2,3'-bipyridineGenerator
MK-663HMDB
ArcoxiaMeSH
Chemical FormulaC18H15ClN2O2S
Average Molecular Weight358.842
Monoisotopic Molecular Weight358.054276131
IUPAC Name5-chloro-3-(4-methanesulfonylphenyl)-2-(6-methylpyridin-3-yl)pyridine
Traditional Nameetoricoxib
CAS Registry Number202409-33-4
SMILES
CC1=NC=C(C=C1)C1=C(C=C(Cl)C=N1)C1=CC=C(C=C1)S(C)(=O)=O
InChI Identifier
InChI=1S/C18H15ClN2O2S/c1-12-3-4-14(10-20-12)18-17(9-15(19)11-21-18)13-5-7-16(8-6-13)24(2,22)23/h3-11H,1-2H3
InChI KeyMNJVRJDLRVPLFE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassBipyridines and oligopyridines
Direct ParentBipyridines and oligopyridines
Alternative Parents
Substituents
  • Bipyridine
  • 3-phenylpyridine
  • Benzenesulfonyl group
  • Methylpyridine
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Sulfone
  • Sulfonyl
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0033 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0033 g/LALOGPS
logP3.7ALOGPS
logP2.79ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)19.69ChemAxon
pKa (Strongest Basic)4.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.04 m³·mol⁻¹ChemAxon
Polarizability36.42 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00c3-1195000000-a6512b3342a7ab34b539JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-f7a7b2b391bf2c553beeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0019000000-ee3806388a3685ebb2eaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-1093000000-f6befa9e036305228b8aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-50b1220eaafc5cd21ae9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0019000000-7f9d7c868b2e84a344d8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-7193000000-02c1e0800c4c34dc4627JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01628 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01628 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01628
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID110209
KEGG Compound IDC11718
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEtoricoxib
METLIN IDNot Available
PubChem Compound123619
PDB ID5CH
ChEBI ID6339
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available