Valdecoxib (CED0006212)

Record Information
Version1.0
Creation Date2016-05-22 04:43:30 UTC
Update Date2026-08-19 14:47:00 UTC
Accession NumberCHEM017900
Identification
Common NameValdecoxib
ClassSmall Molecule
Description
Valdecoxib is an organic compound with the formula C16H14N2O3S and an average molecular weight of 314.36 g/mol. Valdecoxib belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. It is recorded as being found in or released from six sources: household cleaning and consumer products such as other smoking requisites; healthcare, pharmaceuticals and veterinary products, including gynecologicals and antiinflammatory and antirheumatic products; and electrical and electronic equipment, specifically magnets, radio transmission systems, and television systems. The recorded exposure route for this compound is oral. In terms of biological activity, valdecoxib acts on three recorded protein targets, serving as an inhibitor of carbonic anhydrase 2 (CA2), carbonic anhydrase 3 (CA3), and prostaglandin G/H synthase 2 (PTGS2). Regarding its health effects, the compound is used as a treatment for inflammation (PMC11226812).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamideChEBI
BextraChEBI
p-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamideChEBI
ValdecoxibumChEBI
4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulphonamideGenerator
p-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulphonamideGenerator
COXHMDB
KudeqHMDB
ValdynHMDB
ValecoxibHMDB
Pfizer brand OF valdecoxibHMDB
Chemical FormulaC16H14N2O3S
Average Molecular Mass314.359 g/mol
Monoisotopic Mass314.073 g/mol
CAS Registry Number181695-72-7
IUPAC Name4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzene-1-sulfonamide
Traditional Namevaldecoxib
SMILESCC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)S(N)(=O)=O
InChI IdentifierInChI=1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20)16(18-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H2,17,19,20)
InChI KeyLNPDTQAFDNKSHK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Organosulfonic acid amide
  • Azole
  • Isoxazole
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.035 g/LALOGPS
logP3.32ALOGPS
logP2.82ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)10.06ChemAxon
pKa (Strongest Basic)0.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area86.19 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity84.71 m³·mol⁻¹ChemAxon
Polarizability31.76 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-01qa-0290000000-adad99d8d7c023e6f63bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0089-2930000000-dac70ddadd2ffd150b22Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0439000000-984ffa23e74fb8949b56Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0439000000-8928b5e8f850f43f1430Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0089-2930000000-dac70ddadd2ffd150b22Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0941000000-0931692fec04d3e19f52Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0689000000-764e252bae3ae694704aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0019000000-596b73746ee066f35968Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0049000000-818c4a70e42df2b88f8aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pbi-0390000000-13714d8251c6a02a4053Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0009000000-a2f711c3743b82164d6dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0029000000-2ac37e780c7fe646fc3eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9460000000-fb4b9f778483757805eaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0009000000-fa0317e9dc89d23da23aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0009000000-fa0317e9dc89d23da23aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9611000000-28d2f85d0f3c715b52faNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-bba9fedad3067bb6377eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0039000000-4c17bb46a939879efeeaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6r-2960000000-ea456b0a645f35565a29Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2668.0Log mg/kg[1500:4700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
inflammationis_treatment_forNot AvailablePMC11226812
Exposure Sources
Source IDSourceSectorReference
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
363Antiinflammatory and antirheumatic productsHealthcare, pharmaceuticals & veterinary productsNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
630ToysRecreation & sports surfacesNot Available
Pathways
5 pathways
Valdecoxib Action Pathway
Valdecoxib Action Pathway
Valdecoxib Action Pathway (New)
Valdecoxib Action Pathway (New)
Parecoxib Action Pathway
Parecoxib Action Pathway
Valdecoxib Drug Metabolism Action Pathway
Valdecoxib Drug Metabolism Action Pathway
Valdecoxib Predicted Metabolism Pathway
Valdecoxib Predicted Metabolism Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)2.56902
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)8.95266
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)7.39568
Cytochrome c oxidase subunit 2 structureClick to view 3D structureCytochrome c oxidase subunit 2P00403HumansPredicted (SEA)0.0778492
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)2.33548
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)2.17978
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)7.70707
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)2.80257
Carbonic anhydrase 13 structureClick to view 3D structureCarbonic anhydrase 13Q8N1Q1HumansPredicted (SEA)0.778492
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)6.61718
Click to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)1.08989
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)3.19182
Click to view 3D structureCarbonic anhydraseQ5AJ71Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)Predicted (SEA)1.24559
Click to view 3D structureCarbonic anhydraseQ6FTL6Candida glabrata CBS 138Predicted (SEA)1.79053
Click to view 3D structureDelta carbonic anhydraseQ5U9J1Conticribra weissflogiiPredicted (SEA)0.856341
Click to view 3D structureCarbonate dehydrataseB2V8E3Sulfurihydrogenibium sp. (strain YO3AOP1)Predicted (SEA)1.08989
Click to view 3D structureAstrosclerin-3A6YCJ1Astrosclera willeyanaPredicted (SEA)1.55698
Click to view 3D structureAlpha carbonic anhydraseB5SU02Stylophora pistillataPredicted (SEA)0.934191
Click to view 3D structureCarbonic anhydrase, alpha familyQ31FD6Thiomicrospira crunogenaPredicted (SEA)1.08989
Click to view 3D structureCarbonic anhydraseC0IX24Stylophora pistillataPredicted (SEA)0.934191
Click to view 3D structureCarbonic anhydrase 15Q99N23Mus musculusPredicted (SEA)1.94623
Click to view 3D structureCarbonic anhydrase 4Q95323Bos taurusPredicted (SEA)3.89246
Click to view 3D structurePROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)P96878Mycobacterium tuberculosisPredicted (SEA)2.80257
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)6.15009
Click to view 3D structureAGAP002992-PAQ5TU56Anopheles gambiaePredicted (SEA)0.544945
Concentrations
Not Available
External Links
DrugBank IDDB00580
HMDB IDHMDB0005033
FooDB IDFDB023600
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDCOX
Wikipedia LinkValdecoxib
Chemspider ID106796
ChEBI ID63634
PubChem Compound ID119607
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Rogers, Roland S.; Talley, John J.; Brown, David L.; Nagarajan, Srinivasan; Carter, Jeffery S.; Weier, Richard M.; Stealey, Michael A.; Collins, Paul W.; Seibert, Karen; et al. Substituted isoxazoles for the treatment of inflammation. PCT Int. Appl. (1996), 171 pp. CODEN: PIXXD2 WO 9625405 A1 19960822 CAN 125:247800 AN 1996:601794
2. Rogers, Roland S.; Talley, John J.; Brown, David L.; Nagarajan, Srinivasan; Carter, Jeffery S.; Weier, Richard M.; Stealey, Michael A.; Collins, Paul W.; Seibert, Karen; et al. Substituted isoxazoles for the treatment of inflammation. PCT Int. Appl. (1996), 171 pp. CODEN: PIXXD2 WO 9625405 A1 19960822 CAN 125:247800 AN 1996:601794
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20467258
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20717044
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21073910
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21720517
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21769548