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Record Information
Version3.6
Creation Date2013-06-15 16:58:02 UTC
Update Date2016-02-11 08:08:30 UTC
HMDB IDHMDB60571
Secondary Accession NumbersNone
Metabolite Identification
Common NameCarboxycelecoxib
DescriptionCarboxycelecoxib is a metabolite of celecoxib. Celecoxib INN is a sulfa non-steroidal anti-inflammatory drug (NSAID) and selective COX-2 inhibitor used in the treatment of osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation and menstrual symptoms, and to reduce numbers of colon and rectum polyps in patients with familial adenomatous polyposis. It is marketed by Pfizer. It is known under the brand name Celebrex or Celebra for arthritis and Onsenal for polyps. Celecoxib is available by prescription in capsule form. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H12F3N3O4S
Average Molecular Weight411.355
Monoisotopic Molecular Weight411.050061192
IUPAC Name4-[1-(4-sulfamoylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]benzoic acid
Traditional Name4-[2-(4-sulfamoylphenyl)-5-(trifluoromethyl)pyrazol-3-yl]benzoic acid
CAS Registry NumberNot Available
SMILES
NS(=O)(=O)C1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(C=C1)C(O)=O)C(F)(F)F
InChI Identifier
InChI=1S/C17H12F3N3O4S/c18-17(19,20)15-9-14(10-1-3-11(4-2-10)16(24)25)23(22-15)12-5-7-13(8-6-12)28(21,26)27/h1-9H,(H,24,25)(H2,21,26,27)
InChI KeyInChIKey=WTHNOVFEXONZMI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassPyrazoles
Direct ParentPhenylpyrazoles
Alternative Parents
Substituents
  • Phenylpyrazole
  • Benzenesulfonamide
  • Benzoic acid
  • Benzoic acid or derivatives
  • Benzoyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0032 mg/mLALOGPS
logP3.24ALOGPS
logP3.15ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.98ChemAxon
pKa (Strongest Basic)-0.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area115.28 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.45 m3·mol-1ChemAxon
Polarizability36.17 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Celecoxib Metabolism PathwaySMP00644Not Available
Celecoxib PathwaySMP00096Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00810
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60571
Metagene LinkHMDB60571
METLIN IDNot Available
PubChem Compound10047220
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available