ChemSpider 2D Image | Firocoxib | C17H20O5S

Firocoxib

  • Molecular FormulaC17H20O5S
  • Average mass336.403 Da
  • Monoisotopic mass336.103149 Da
  • ChemSpider ID181008

More details:

Featured data source
The Merck Index Online

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

189954-96-9 [RN]
2(5H)-Furanone, 3-(cyclopropylmethoxy)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)-
2(5H)-Furanone, 3-(cyclopropylmethoxy)-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]- [ACD/Index Name]
3-(Cyclopropylmethoxy)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)furan-2(5H)-one
3-(Cyclopropylmethoxy)-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanon [German] [ACD/IUPAC Name]
3-(Cyclopropylmethoxy)-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanone [ACD/IUPAC Name]
3-(Cyclopropylméthoxy)-5,5-diméthyl-4-[4-(méthylsulfonyl)phényl]-2(5H)-furanone [French] [ACD/IUPAC Name]
3-(cyclopropylmethoxy)-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]furan-2(5H)-one
3-Cyclopropylmethoxy-4-(4-methanesulfonylphenyl)-5,5-dimethyl-5H-furan-2-one
Equioxx [Trade name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

8335837 [DBID]
8359 [DBID]
ML-1,785,713 [DBID]
D03712 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      An enol ether that is the cyclopropylmethyl ether of 3-hydroxy-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]furan-2-one. A selective cyclooxygenase 2 inhibitor, it is used in veterinary medicine for the c ontrol of pain and inflammation associated with osteoarthritis in horses and dogs. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:76136, CHEBI:76136

    • Bio Activity:

      COX MedChem Express HY-14670
      Firocoxib(ML 1785713) is a potent and selective cyclooxygenase (COX)-2 inhibitor with IC50 of 0.13 uM, 58 fold sensitivity for COX2 VSCOX1. MedChem Express
      Firocoxib(ML 1785713) is a potent and selective cyclooxygenase (COX)-2 inhibitor with IC50 of 0.13 uM, 58 fold sensitivity for COX2 VSCOX1.; IC50 value: 0.13 uM [1]; Target: COX2 inhibitor; in vitro: Blood concentrations resulting in 50% inhibition of COX-1 and COX-2 activity in vitro were 75 +/- 2 microM and 0.13 +/- 0.03 microM, respectively, and selectivity for inhibiting COX-2 relative to COX-1 was 58. MedChem Express HY-14670
      Firocoxib(ML 1785713) is a potent and selective cyclooxygenase (COX)-2 inhibitor with IC50 of 0.13 uM, 58 fold sensitivity for COX2 VSCOX1.;IC50 value: 0.13 uM [1];Target: COX2 inhibitor;In vitro: Blood concentrations resulting in 50% inhibition of COX-1 and COX-2 activity in vitro were 75 +/- 2 microM and 0.13 +/- 0.03 microM, respectively, and selectivity for inhibiting COX-2 relative to COX-1 was 58. Firocoxib had moderate to high oral bioavailability (54% to 70%), low plasma clearance (4.7 to 5.8 mL/min/kg), and an elimination half-life of 8.7 to 12.2 hours [1]. ;In vivo: Administration of firocoxib did not cause any adverse effects on GI, or hematological or serum biochemical variables and appears to have been well tolerated by dogs [2]. Firocoxib (0.5 mg/kg) was initially administered i.v. to calves, and following a 14-day washout period, animals received firocoxib orally prior to cautery dehorning. Firocoxib concentrations were determined by liquid chromatography-tandem mas MedChem Express HY-14670
      Immunology/Inflammation MedChem Express HY-14670
      Immunology/Inflammation; MedChem Express HY-14670

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

Density: 1.3±0.1 g/cm3
Boiling Point: 563.9±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 84.7±3.0 kJ/mol
Flash Point: 294.8±30.1 °C
Index of Refraction: 1.584
Molar Refractivity: 85.5±0.4 cm3
#H bond acceptors: 5
#H bond donors: 0
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 1.23
ACD/LogD (pH 5.5): 1.76
ACD/BCF (pH 5.5): 12.80
ACD/KOC (pH 5.5): 215.84
ACD/LogD (pH 7.4): 1.76
ACD/BCF (pH 7.4): 12.80
ACD/KOC (pH 7.4): 215.84
Polar Surface Area: 78 Å2
Polarizability: 33.9±0.5 10-24cm3
Surface Tension: 51.5±5.0 dyne/cm
Molar Volume: 255.2±5.0 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) =  1.26

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  476.78  (Adapted Stein & Brown method)
    Melting Pt (deg C):  201.24  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.45E-009  (Modified Grain method)
    Subcooled liquid VP: 1.06E-007 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):  625.2
       log Kow used: 1.26 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  432.56 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.43E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.027E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.26  (KowWin est)
  Log Kaw used:  -8.463  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.723
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2303
   Biowin2 (Non-Linear Model)     :   0.0551
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3752  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4282  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2596
   Biowin6 (MITI Non-Linear Model):   0.0416
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3786
 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):  1.41E-005 Pa (1.06E-007 mm Hg)
  Log Koa (Koawin est  ): 9.723
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.212 
       Octanol/air (Koa) model:  0.0013 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.885 
       Mackay model           :  0.944 
       Octanol/air (Koa) model:  0.094 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  47.5571 E-12 cm3/molecule-sec
      Half-Life =     0.225 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.699 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    25.199999 E-17 cm3/molecule-sec
      Half-Life =     0.045 Days (at 7E11 mol/cm3)
      Half-Life =      1.091 Hrs
   Fraction sorbed to airborne particulates (phi): 0.915 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  330.2
      Log Koc:  2.519 

 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 = 0.272 (BCF = 1.87)
       log Kow used: 1.26 (estimated)

 Volatilization from Water:
    Henry LC:  8.43E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.274E+007  hours   (5.308E+005 days)
    Half-Life from Model Lake :  1.39E+008  hours   (5.79E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               1.92  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.83  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       0.0105          0.908        1000       
   Water     38.3            900          1000       
   Soil      61.6            1.8e+003     1000       
   Sediment  0.087           8.1e+003     0          
     Persistence Time: 1e+003 hr

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