ChemSpider 2D Image | Febuxostat | C16H16N2O3S


  • Molecular FormulaC16H16N2O3S
  • Average mass316.375 Da
  • Monoisotopic mass316.088165 Da
  • ChemSpider ID118173

More details:

Featured data source

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

144060-53-7 [RN]
2-(3-Cyan-4-isobutoxyphenyl)-4-methyl-1,3-thiazol-5-carbonsäure [German] [ACD/IUPAC Name]
2-(3-Cyano-4-(2-methylpropoxy)phenyl)-4-methylthiazole-5-carboxylic acid
2-(3-Cyano-4-isobutoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylic acid [ACD/IUPAC Name]
2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylic acid
2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid
5-Thiazolecarboxylic acid, 2-(3-cyano-4-(2-methylpropoxy)phenyl)-4-methyl-
5-Thiazolecarboxylic acid, 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl- [ACD/Index Name]
Acide 2-(3-cyano-4-isobutoxyphényl)-4-méthyl-1,3-thiazole-5-carboxylique [French] [ACD/IUPAC Name]
febuxostat [Spanish] [INN]

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

D01206 [DBID]
TEI 6720 [DBID]
TEI-6720 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1175
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1175
      no pictogram Axon Medchem 1175
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1175
      P261; P262 Biosynth Q-100164
      R22 LKT Labs [F1607]
      Warning Axon Medchem 1175
      Xn LKT Labs [F1607]
    • Target Organs:

      Xanthine Oxidase inhibitor TargetMol T0773
    • Bio Activity:

      Enzymes Tocris Bioscience 4427
      Febuxostat(TEI 6720;TMX 67 ) is selective xanthine oxidase inhibitor with Ki of 0.6 nM. MedChem Express
      Febuxostat(TEI 6720;TMX 67 ) is selective xanthine oxidase inhibitor with Ki of 0.6 nM.;IC50 value: 0.6 nM (Ki) [1];Target: xanthine oxidase;In vitro: Febuxostat displays potent mixed-type inhibition of the activity of purified bovine milk xanthine oxidase, with Ki and Ki' values of 0.6 nM and 3.1 nM respectively, indicating inhibition of both the oxidized and reduced forms of xanthine oxidase [1]. ;In vivo: Febuxostat (5?6 mg/kg/day) combined with fructose significantly lowers blood pressure, UA, triglycerides, and insulin in rats compared with fructose alone. Febuxostat (5?6 mg/kg/day) combined with fructose also reduces glomerular pressure, renal vasoconstriction, and afferent arteriolar area in rats compared with fructose alone [2]. Febuxostat prevents hyperuricemia in 5/6 nephrectomy (5/6 Nx)+oxonic acid (OA)+Febuxostat(Fx) rats and ameliorates proteinuria, preserves renal function and prevents glomerular hypertension in both 5/6 nephrectomy (5/6 Nx)+vehicle (V)+Febuxostat(Fx MedChem Express HY-14268
      Metabolism TargetMol T0773
      Metabolism/Protease; MedChem Express HY-14268
      Non-purine inhibitor of xanthine oxidase (Ki = 1.2 nM). Binds to a channel leading to the enzyme active site; obstructs substrate binding. Tocris Bioscience 4427
      Other Oxygenases/Oxidases Tocris Bioscience 4427
      Oxygenases/Oxidases Tocris Bioscience 4427
      Reduces the production of uric acid;; Used in the treatment of chronic gout and hyperuricemia InterBioScreen [Bio-0984]
      Xanthine oxidase MedChem Express HY-14268
      Xanthine oxidase TargetMol T0773
      Xanthine oxidase inhibitor Tocris Bioscience 4427
      Xanthine oxidase/xanthine dehydrogenase inhibitor InterBioScreen [Bio-0984]

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

Density: 1.3±0.1 g/cm3
Boiling Point: 536.6±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 85.6±3.0 kJ/mol
Flash Point: 278.3±32.9 °C
Index of Refraction: 1.606
Molar Refractivity: 83.1±0.4 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 4.87
ACD/LogD (pH 5.5): 1.02
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 4.51
ACD/LogD (pH 7.4): 0.69
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 2.07
Polar Surface Area: 111 Å2
Polarizability: 32.9±0.5 10-24cm3
Surface Tension: 63.8±5.0 dyne/cm
Molar Volume: 241.0±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) =  4.21

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  488.18  (Adapted Stein & Brown method)
    Melting Pt (deg C):  207.08  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.41E-010  (Modified Grain method)
    Subcooled liquid VP: 5.45E-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):  1.348
       log Kow used: 4.21 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.45109 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.74E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.980E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.21  (KowWin est)
  Log Kaw used:  -12.447  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.657
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2674
   Biowin2 (Non-Linear Model)     :   0.9998
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3725  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3424  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4805
   Biowin6 (MITI Non-Linear Model):   0.1722
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.3226
 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):  7.27E-006 Pa (5.45E-008 mm Hg)
  Log Koa (Koawin est  ): 16.657
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.413 
       Octanol/air (Koa) model:  1.11E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.937 
       Mackay model           :  0.971 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  18.9009 E-12 cm3/molecule-sec
      Half-Life =     0.566 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     6.791 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.954 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1112
      Log Koc:  3.046 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 4.21 (estimated)

 Volatilization from Water:
    Henry LC:  8.74E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.192E+011  hours   (4.965E+009 days)
    Half-Life from Model Lake :   1.3E+012  hours   (5.416E+010 days)

 Removal In Wastewater Treatment:
    Total removal:              40.46  percent
    Total biodegradation:        0.40  percent
    Total sludge adsorption:    40.06  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       1.44e-006       13.6         1000       
   Water     10.6            900          1000       
   Soil      85.3            1.8e+003     1000       
   Sediment  4.09            8.1e+003     0          
     Persistence Time: 1.92e+003 hr


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