ChemSpider 2D Image | Rofecoxib | C17H14O4S

Rofecoxib

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

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Featured data source



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

0QTW8Z7MCR
162011-90-7 [RN]
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-(p-(Methylsulfonyl)phenyl)-3-phenyl-2(5H)-furanone
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]
4-[4-(methylsulfonyl)phenyl]-3-phenylfuran-2(5H)-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

MK 996 [DBID]
C07590 [DBID]
CCRIS 8967 [DBID]
CHEBI:8887 [DBID]
D00568 [DBID]
DivK1c_006765 [DBID]
HSDB 7262 [DBID]
KBio1_001709 [DBID]
KBio2_000559 [DBID]
KBio2_002345 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

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

      COX inhibitor;Elastin;MRP inhibitor TargetMol T1185
    • Chemical Class:

      A butenolide that is furan-2(5<element>H</element>)-one substituted by a phenyl group at position 3 and by a <ital>p</ital>-(methylsulfonyl)phenyl group at position 4. A selective cyclooxygenase 2 inh ibitor, it was used from 1999 to 2004 for the treatment of ostoarthritis, but was withdrawn following concerns about an associated increased risk of heart attack and stroke. ChEBI CHEBI:8887
    • Drug Status:

      INN, BAN Microsource [01504235]
      USAN, INN, BAN Microsource [01504235]
      withdrawn BIONET-Key Organics KS-1107
    • 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:
       Acrylates

 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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