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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-17 10:02:55 UTC
Update Date2020-02-26 21:25:41 UTC
HMDB IDHMDB0005033
Secondary Accession Numbers
  • HMDB05033
Metabolite Identification
Common NameValdecoxib
DescriptionValdecoxib, also known as bextra or kudeq, 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. A former Pfizer district sales manager was indicted and sentenced to home confinement for destroying documents regarding the illegal promotion of Bextra. Valdecoxib is a drug which is used for the treatment of osteoarthritis and dysmenorrhoea. Valdecoxib is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, valdecoxib is involved in valdecoxib action pathway. Valdecoxib has analytical methods for bioequivalence studies, metabolite determination, estimation of formulation, and an HPTLC method for simultaneous estimation in tablet dosage form. Pfizer first acknowledged cardiovascular risks associated with Bextra in October 2004. and was available by prescription in tablet form until 2005 when the FDA requested that Pfizer withdraw Bextra from the American market. In the United States, the Food and Drug Administration (FDA) approved valdecoxib for the treatment of osteoarthritis, adult rheumatoid arthritis, and primary dysmenorrhea. Six whistle-blowers were awarded more than $102 million for their role in the investigation.
Structure
Data?1582752341
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 Weight314.359
Monoisotopic Molecular Weight314.072513014
IUPAC Name4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzene-1-sulfonamide
Traditional Namevaldecoxib
CAS Registry Number181695-72-7
SMILES
CC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)S(N)(=O)=O
InChI Identifier
InChI=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
Ontology
Disposition

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point160 - 162 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.10231661259
DarkChem[M-H]-169.58331661259
DeepCCS[M+H]+172.65130932474
DeepCCS[M-H]-170.29330932474
DeepCCS[M-2H]-203.68930932474
DeepCCS[M+Na]+178.91530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ValdecoxibCC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)S(N)(=O)=O4513.1Standard polar33892256
ValdecoxibCC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)S(N)(=O)=O2894.1Standard non polar33892256
ValdecoxibCC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)S(N)(=O)=O2954.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Valdecoxib,1TMS,isomer #1CC1=C(C2=CC=C(S(=O)(=O)N[Si](C)(C)C)C=C2)C(C2=CC=CC=C2)=NO12953.0Semi standard non polar33892256
Valdecoxib,1TMS,isomer #1CC1=C(C2=CC=C(S(=O)(=O)N[Si](C)(C)C)C=C2)C(C2=CC=CC=C2)=NO12784.6Standard non polar33892256
Valdecoxib,1TMS,isomer #1CC1=C(C2=CC=C(S(=O)(=O)N[Si](C)(C)C)C=C2)C(C2=CC=CC=C2)=NO13954.0Standard polar33892256
Valdecoxib,2TMS,isomer #1CC1=C(C2=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2)C(C2=CC=CC=C2)=NO12875.2Semi standard non polar33892256
Valdecoxib,2TMS,isomer #1CC1=C(C2=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2)C(C2=CC=CC=C2)=NO12961.2Standard non polar33892256
Valdecoxib,2TMS,isomer #1CC1=C(C2=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2)C(C2=CC=CC=C2)=NO13830.3Standard polar33892256
Valdecoxib,1TBDMS,isomer #1CC1=C(C2=CC=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)C=C2)C(C2=CC=CC=C2)=NO13165.0Semi standard non polar33892256
Valdecoxib,1TBDMS,isomer #1CC1=C(C2=CC=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)C=C2)C(C2=CC=CC=C2)=NO13024.5Standard non polar33892256
Valdecoxib,1TBDMS,isomer #1CC1=C(C2=CC=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)C=C2)C(C2=CC=CC=C2)=NO13903.9Standard polar33892256
Valdecoxib,2TBDMS,isomer #1CC1=C(C2=CC=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C(C2=CC=CC=C2)=NO13362.3Semi standard non polar33892256
Valdecoxib,2TBDMS,isomer #1CC1=C(C2=CC=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C(C2=CC=CC=C2)=NO13406.3Standard non polar33892256
Valdecoxib,2TBDMS,isomer #1CC1=C(C2=CC=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C(C2=CC=CC=C2)=NO13789.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Valdecoxib GC-MS (Non-derivatized) - 70eV, Positivesplash10-01qa-0290000000-adad99d8d7c023e6f63b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Valdecoxib GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Valdecoxib LC-ESI-qTof , Positive-QTOFsplash10-0089-2930000000-dac70ddadd2ffd150b222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valdecoxib , positive-QTOFsplash10-014i-0439000000-984ffa23e74fb8949b562017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valdecoxib , positive-QTOFsplash10-014i-0439000000-8928b5e8f850f43f14302017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valdecoxib , positive-QTOFsplash10-0089-2930000000-dac70ddadd2ffd150b222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valdecoxib 35V, Positive-QTOFsplash10-001i-0941000000-0931692fec04d3e19f522021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valdecoxib 35V, Negative-QTOFsplash10-03di-0689000000-764e252bae3ae694704a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valdecoxib 10V, Positive-QTOFsplash10-014i-0019000000-596b73746ee066f359682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valdecoxib 20V, Positive-QTOFsplash10-014i-0049000000-818c4a70e42df2b88f8a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valdecoxib 40V, Positive-QTOFsplash10-0pbi-0390000000-13714d8251c6a02a40532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valdecoxib 10V, Negative-QTOFsplash10-03di-0009000000-a2f711c3743b82164d6d2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valdecoxib 20V, Negative-QTOFsplash10-03di-0029000000-2ac37e780c7fe646fc3e2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valdecoxib 40V, Negative-QTOFsplash10-004i-9460000000-fb4b9f778483757805ea2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valdecoxib 10V, Negative-QTOFsplash10-03di-0009000000-fa0317e9dc89d23da23a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valdecoxib 20V, Negative-QTOFsplash10-03di-0009000000-fa0317e9dc89d23da23a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valdecoxib 40V, Negative-QTOFsplash10-004i-9611000000-28d2f85d0f3c715b52fa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valdecoxib 10V, Positive-QTOFsplash10-014i-0009000000-bba9fedad3067bb6377e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valdecoxib 20V, Positive-QTOFsplash10-014i-0039000000-4c17bb46a939879efeea2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valdecoxib 40V, Positive-QTOFsplash10-0a6r-2960000000-ea456b0a645f35565a292021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00580
Phenol Explorer Compound IDNot Available
FooDB IDFDB023600
KNApSAcK IDNot Available
Chemspider ID106796
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkValdecoxib
METLIN IDNot Available
PubChem Compound119607
PDB IDCOX
ChEBI ID63634
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceRogers, 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
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

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
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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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