ChemSpider 2D Image | Rofecoxib | C17H14O4S


  • Molecular FormulaC17H14O4S
  • Average mass314.356 Da
  • Monoisotopic mass314.061279 Da
  • ChemSpider ID4911

More details:

Featured data source

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

2(5H)-Furanone, 4-(4-(methylsulfonyl)phenyl)-3-phenyl-
2(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- [ACD/Index Name]
2(5H)-Furanone, 4-[4-(methyl-sulfonyl)phenyl]-3-phenyl-
4-[4-(Methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanon [German] [ACD/IUPAC Name]
4-[4-(Methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanone [ACD/IUPAC Name]
4-[4-(Méthylsulfonyl)phényl]-3-phényl-2(5H)-furanone [French] [ACD/IUPAC Name]
Ceeoxx [Trade name]
Ceoxx [Trade name]

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

MK 996 [DBID]
C07590 [DBID]
D00568 [DBID]
DivK1c_006765 [DBID]
HSDB 7262 [DBID]
KBio1_001709 [DBID]
KBio2_000559 [DBID]
KBio2_002345 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 097025
      P261; P262 Biosynth Q-201676
    • Target Organs:

      COX inhibitor;Elastin;MRP inhibitor TargetMol T1185
    • Drug Status:

      INN, BAN Microsource [01504235]
      USAN, INN, BAN Microsource [01504235]
    • Compound Source:

      synthetic Microsource [01504235]
    • Bio Activity:

      COX MedChem Express HY-17372
      Immunology/Inflammation; MedChem Express HY-17372
      Neuroscience TargetMol T1185
      Nonsteroidal anti-inflammatory drug (NSAID) Zerenex Molecular [ZBioX-0087]
      Prostaglandin G/H synthase 2;Elastin;MRAP4 TargetMol T1185
      Rofecoxib(MK 966) is a potent inhibitor of the COX-2-dependent production of PGE2 in human osteosarcoma cells (IC50= 26?10 nM) and Chinese hamster ovary cells expressing human COX-2 (IC50=18?7 nM).;IC50 value: 26 nM (cell assay);Target: COX2Rofecoxib is a synthetic, nonsteroidal derivative of phenyl-furanone with antiinflammatory, antipyretic and analgesic properties and potential antineoplastic properties. Rofecoxib binds to and inhibits the enzyme cyclooxygenase-2 (COX-2), resulting in an inhibition of the conversion of arachidonic acid to prostaglandins. COX-related metabolic pathways may represent key regulators of cell proliferation and neo-angiogenesis. Some epithelial tumor cell types overexpress pro-angiogenic COX-2. Rofecoxib was used as an anti-inflammatory analgesic which has now been withdrawn from the market because of its association with cardiovascular problems. MedChem Express HY-17372
      Rofecoxib(MK 966) is a potent inhibitor of the COX-2-dependent production of PGE2 in human osteosarcoma cells (IC50= 26±10 nM) and Chinese hamster ovary cells expressing human COX-2 (IC50=18±7 nM). MedChem Express
  • Gas Chromatography

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.3±0.1 g/cm3
Boiling Point: 577.6±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 86.5±3.0 kJ/mol
Flash Point: 303.1±30.1 °C
Index of Refraction: 1.619
Molar Refractivity: 82.7±0.4 cm3
#H bond acceptors: 4
#H bond donors: 0
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 1.34
ACD/LogD (pH 5.5): 2.07
ACD/BCF (pH 5.5): 22.17
ACD/KOC (pH 5.5): 319.84
ACD/LogD (pH 7.4): 2.07
ACD/BCF (pH 7.4): 22.17
ACD/KOC (pH 7.4): 319.84
Polar Surface Area: 69 Å2
Polarizability: 32.8±0.5 10-24cm3
Surface Tension: 51.7±3.0 dyne/cm
Molar Volume: 235.7±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) =  1.58

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  486.77  (Adapted Stein & Brown method)
    Melting Pt (deg C):  199.22  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.62E-010  (Modified Grain method)
    Subcooled liquid VP: 5.92E-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):  455.2
       log Kow used: 1.58 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  53.58 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.23E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.833E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.58  (KowWin est)
  Log Kaw used:  -9.040  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.620
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9002
   Biowin2 (Non-Linear Model)     :   0.9881
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6667  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6280  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2148
   Biowin6 (MITI Non-Linear Model):   0.0592
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1677
 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):  7.89E-006 Pa (5.92E-008 mm Hg)
  Log Koa (Koawin est  ): 10.620
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.38 
       Octanol/air (Koa) model:  0.0102 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.932 
       Mackay model           :  0.968 
       Octanol/air (Koa) model:  0.45 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  42.7423 E-12 cm3/molecule-sec
      Half-Life =     0.250 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.003 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =   163.799988 E-17 cm3/molecule-sec
      Half-Life =     0.007 Days (at 7E11 mol/cm3)
      Half-Life =     10.075 Min
   Fraction sorbed to airborne particulates (phi): 0.95 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  7667
      Log Koc:  3.885 

 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 = 0.514 (BCF = 3.267)
       log Kow used: 1.58 (estimated)

 Volatilization from Water:
    Henry LC:  2.23E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.655E+007  hours   (1.94E+006 days)
    Half-Life from Model Lake : 5.078E+008  hours   (2.116E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               2.00  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.91  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       0.00349         0.163        1000       
   Water     33.7            900          1000       
   Soil      66.2            1.8e+003     1000       
   Sediment  0.0895          8.1e+003     0          
     Persistence Time: 1e+003 hr


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