ChemSpider 2D Image | Valdecoxib | C16H14N2O3S

Valdecoxib

  • Molecular FormulaC16H14N2O3S
  • Average mass314.359 Da
  • Monoisotopic mass314.072510 Da
  • ChemSpider ID106796

More details:

Featured data source
The Merck Index Online

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

181695-72-7 [RN]
2919279Q3W
4-(5-Methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide [ACD/IUPAC Name]
4-(5-Méthyl-3-phényl-1,2-oxazol-4-yl)benzènesulfonamide [French] [ACD/IUPAC Name]
4-(5-Methyl-3-phenyl-1,2-oxazol-4-yl)benzolsulfonamid [German] [ACD/IUPAC Name]
4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide
4-(5-Methyl-3-phenylisoxazol-4-yl)benzenesulfonamide
4-(5-Méthyl-3-phénylisoxazol-4-yl)benzènesulfonamide [French]
4-(5-Methyl-3-phenylisoxazol-4-yl)benzolsulfonamid
Benzenesulfonamide, 4-(5-methyl-3-phenyl-4-isoxazolyl)- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

7815 [DBID]
CHEBI:63634 [DBID]
D02709 [DBID]
EPA Pesticide Chemical Code 079011 [DBID]
HSDB 7302 [DBID]
KBio2_002227 [DBID]
KBio2_004795 [DBID]
KBio2_007363 [DBID]
KBio3_001941 [DBID]
KBioGR_001617 [DBID]
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  • Experimental Physico-chemical Properties

    • Experimental Solubility:

      DMSO 124 mg/mL (199 mM); Water <1 mg/mL (<1 mM) MedChem Express HY-15762
      DMSO 63 mg/mL; Water <1 mg/mL; Ethanol 18 mg/mL MedChem Express HY-15762
      Soluble to 100 mM in DMSO Tocris Bioscience 4206
  • Miscellaneous

    • Safety:

      M01AH03 Wikidata Q347613
      Sold for research purposes under agreement from Pfizer Inc. Tocris Bioscience 4206

    • Target Organs:

      COX inhibitor TargetMol T0219

    • Chemical Class:

      A member of the class of isoxazoles that is isoxazole which is substituted at positions 3, 4 and 5 by phenyl, <ital>p</ital>-sulfamoylphenyl and methyl groups, respectively. A selective cyclooxygenase 2-inhibitor, it used as a nonsteroidal anti-inflammatory drug (NSAID) for the treatment of arthritis from 2001 until 2005, when it was withdrawn following concerns of an associated increased risk of heart attack and stroke. ChEBI CHEBI:63634
      A member of the class of isoxazoles that is isoxazole which is substituted at positions 3, 4 and 5 by phenyl, p-sulfamoylphenyl and methyl groups, respectively. A selective cyclooxygenase 2-inhibitor, it used as a nonsteroidal anti-inflammatory drug (NSAID) for the treatment of arthritis from 2001 until 2005, when it was withdrawn following concerns of an associated increased risk of heart attack and stroke. ChEBI CHEBI:63634

    • Bio Activity:

      COX MedChem Express HY-15762
      Cyclooxygenase Tocris Bioscience 4206
      Enzymes Tocris Bioscience 4206
      Immunology/Inflammation MedChem Express HY-15762
      Immunology/Inflammation; MedChem Express HY-15762
      Neuroscience TargetMol T0219
      Oxygenases/Oxidases Tocris Bioscience 4206
      Prostaglandin G/H synthase TargetMol T0219
      Selective and potent COX-2 inhibitor Tocris Bioscience 4206
      Selective and potent COX-2 inhibitor (in vitro IC50 values are 0.005 and 140 ?M for human recombinant COX-2 and COX-1 respectively). Displays potent anti-inflammatory activity in vivo. Tocris Bioscience 4206
      Selective and potent COX-2 inhibitor (in vitro IC50 values are 0.005 and 140 muM for human recombinant COX-2 and COX-1 respectively). Displays potent anti-inflammatory activity in vivo. Tocris Bioscience 4206
      Valdecoxib (SC 65872) is a COX-2 selective inhibitor with an IC50 value of 5 nM. MedChem Express
      Valdecoxib (SC 65872) is a COX-2 selective inhibitor with an IC50 value of 5 nM.; IC50 Value: 5 nM (COX-2) [1]; Target: COX-2; Valdecoxib is a non-steroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, and painful menstruation and menstrual symptoms. MedChem Express HY-15762
      Valdecoxib (SC 65872) is a COX-2 selective inhibitor with an IC50 value of 5 nM.;IC50 Value: 5 nM (COX-2) [1];Target: COX-2Valdecoxib is a non-steroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, and painful menstruation and menstrual symptoms. ;In vitro: The overall saturation binding affinity for COX-2 of valdecoxib is 2.6 nM (compared with 1.6 nM for celecoxib, 51 nM for rofecoxib, and 260 nM for etoricoxib), with a slow off-rate (t(1/2) approximately 98 min). Valdecoxib inhibits COX-1 in a competitive fashion only at very high concentrations (IC(50) = 150 microM). Collectively, these data provide a mechanistic basis for the potency and in vitro selectivity of valdecoxib for COX-2. Valdecoxib showed similar activity in the human whole-blood COX assay (COX-2 IC(50) = 0.24 microM; COX-1 IC(50) = 21.9 microM) [1]. The affinity of [(3)H]celecoxib for COX-2 (K(D) = 2.3 nM) was similar to the affinity of [(3)H]valdecoxib (K(D) = 3.2 MedChem Express HY-15762
  • Gas Chromatography

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.3±0.1 g/cm3
Boiling Point: 481.2±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 74.6±3.0 kJ/mol
Flash Point: 244.8±31.5 °C
Index of Refraction: 1.609
Molar Refractivity: 83.5±0.4 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 1.71
ACD/LogD (pH 5.5): 2.54
ACD/BCF (pH 5.5): 50.37
ACD/KOC (pH 5.5): 575.45
ACD/LogD (pH 7.4): 2.54
ACD/BCF (pH 7.4): 50.19
ACD/KOC (pH 7.4): 573.38
Polar Surface Area: 95 Å2
Polarizability: 33.1±0.5 10-24cm3
Surface Tension: 51.5±3.0 dyne/cm
Molar Volume: 241.2±3.0 cm3

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™ 

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  2.67

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  492.82  (Adapted Stein & Brown method)
    Melting Pt (deg C):  209.25  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.62E-010  (Modified Grain method)
    Subcooled liquid VP: 4.17E-008 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  53.34
       log Kow used: 2.67 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  6.6285 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.22E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.583E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.67  (KowWin est)
  Log Kaw used:  -9.042  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.712
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7806
   Biowin2 (Non-Linear Model)     :   0.7152
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4516  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3306  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1077
   Biowin6 (MITI Non-Linear Model):   0.0057
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1764
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  5.56E-006 Pa (4.17E-008 mm Hg)
  Log Koa (Koawin est  ): 11.712
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.54 
       Octanol/air (Koa) model:  0.126 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.951 
       Mackay model           :  0.977 
       Octanol/air (Koa) model:  0.91 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  13.3476 E-12 cm3/molecule-sec
      Half-Life =     0.801 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     9.616 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.964 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.941E+005
      Log Koc:  5.288 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.354 (BCF = 22.58)
       log Kow used: 2.67 (estimated)

 Volatilization from Water:
    Henry LC:  2.22E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.676E+007  hours   (1.948E+006 days)
    Half-Life from Model Lake : 5.101E+008  hours   (2.125E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               3.68  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.58  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.00531         19.2         1000       
   Water     14.7            900          1000       
   Soil      85.2            1.8e+003     1000       
   Sediment  0.166           8.1e+003     0          
     Persistence Time: 1.7e+003 hr

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