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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-10-17 10:02:55 UTC
Update Date2019-07-23 05:46:40 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. Valdecoxib is a drug which is used for the treatment of osteoarthritis and dysmenorrhoea. Unlike celecoxib, valdecoxib lacks a sulfonamide chain and does not require CYP450 enzymes for metabolism. Valdecoxib is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, valdecoxib is involved in valdecoxib action pathway. Valdecoxib was removed from the Canadian, U.S., and E.U. markets in 2005 due to concerns about possible increased risk of heart attack and stroke. Valdecoxib selectively inhibits the cyclooxygenase-2 (COX-2) enzyme, important for the mediation of inflammation and pain. Symptoms following acute NSAID overdoses are usually limited to lethargy, drowsiness, nausea, vomiting, and epigastric pain, which are generally reversible with supportive care. Hypertension, acute renal failure, respiratory depression and coma may occur, but are rare. Valdecoxib, a selective cyclooxygenase-2 (COX-2) inhibitor, is classified as a nonsteroidal anti-inflammatory drug (NSAID). Valdecoxib is a prescription drug used in the treatment of osteoarthritis, rheumatoid arthritis, and painful menstruation and menstrual symptoms.
Structure
Data?1563860800
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:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point160 - 162 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01qa-0290000000-adad99d8d7c023e6f63bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0089-2930000000-dac70ddadd2ffd150b22Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0439000000-984ffa23e74fb8949b56Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0439000000-8928b5e8f850f43f1430Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0089-2930000000-dac70ddadd2ffd150b22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0019000000-596b73746ee066f35968Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0049000000-818c4a70e42df2b88f8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-0390000000-13714d8251c6a02a4053Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-a2f711c3743b82164d6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0029000000-2ac37e780c7fe646fc3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9460000000-fb4b9f778483757805eaSpectrum
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
FoodDB 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
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