ChemSpider 2D Image | Leflunomide | C12H9F3N2O2

Leflunomide

  • Molecular FormulaC12H9F3N2O2
  • Average mass270.207 Da
  • Monoisotopic mass270.061615 Da
  • ChemSpider ID3762

More details:



Featured data source



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

4-Isoxazolecarboxamide, 5-methyl-N-[4-(trifluoromethyl)phenyl]- [ACD/Index Name]
5079
5-Methyl-N-[4-(trifluormethyl)phenyl]-1,2-oxazol-4-carboxamid [German] [ACD/IUPAC Name]
5-Methyl-N-[4-(trifluormethyl)phenyl]isoxazol-4-carboxamid
5-Methyl-N-[4-(trifluoromethyl)phenyl]-1,2-oxazole-4-carboxamide [ACD/IUPAC Name]
5-Méthyl-N-[4-(trifluorométhyl)phényl]-1,2-oxazole-4-carboxamide [French] [ACD/IUPAC Name]
5-methyl-N-[4-(trifluoromethyl)phenyl]isoxazole-4-carboxamide
5-méthyl-N-[4-(trifluorométhyl)phényl]isoxazole-4-carboxamide
75706-12-6 [RN]
G162GK9U4W
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

A 771726 [DBID]
AIDS009747 [DBID]
AIDS-009747 [DBID]
AP-501/42475599 [DBID]
C07905 [DBID]
CHEBI:6402 [DBID]
D00749 [DBID]
DivK1c_000916 [DBID]
EU-0100649 [DBID]
HSDB 7289 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      22-36/37/38 LKT Labs [L1817]
      Danger Biosynth Q-201289
      GHS06 Biosynth Q-201289
      H301; H315; H319; H335 Biosynth Q-201289
      H302 H315 H335 H319 LKT Labs [L1817]
      IRRITANT Matrix Scientific 078298
      L04AA13 Wikidata Q248550
      P261; P301+P310; P305+P351+P338 Biosynth Q-201289
      Xn, Xi LKT Labs [L1817]
    • Target Organs:

      Protein-tyrosine kinase 2 antagonist;AhR agonist;Dehydrogenase inhibitor TargetMol T1159
    • Chemical Class:

      A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 5-methyl-1,2-oxazole-4-carboxylic acid with the anilino group of 4-(trifluoromethyl)aniline. The prodrug of teriflun omide. ChEBI CHEBI:6402
    • Drug Status:

      approved BIONET-Key Organics KS-1076
    • Compound Source:

      synthetic Microsource [01503927]
      synthetic; SU-101; HWA-486 Microsource [01503927]
    • Bio Activity:

      Dehydrogenases Tocris Bioscience 2228
      Dihydroorotate dehydrogenase inhibitor Tocris Bioscience 2228
      Dihyroorotate Dehydrogenase Tocris Bioscience 2228
      Enzyme TargetMol T1159
      Enzymes Tocris Bioscience 2228
      Inhibitor of DHODH Tocris Bioscience 2228
      Inhibitor of dihydroorotate dehydrogenase (IC50 = 2.5 ?M). Inhibits de novo pyrimidine synthesis in human T cells in vitro; also inhibits lymphocyte proliferation. Exhibits efficacy in several animal models of autoimmune disease, arthritis and graft rejection. Active metabolite, teriflunomide (A77 1726, Cat. No. 5069), also available. Tocris Bioscience 2228
      Inhibitor of dihydroorotate dehydrogenase (IC50 = 2.5 ?M). Inhibits de novo pyrimidine synthesis in human T cells in vitro; also inhibits lymphocyte proliferation. Exhibits efficacy in several animal models of autoimmune disease, arthritis and graft rejection. Active metabolite, teriflunomide (A77 1726, Cat. No. 5069), also available. Tocris Bioscience 2228
      Inhibitor of dihydroorotate dehydrogenase (IC50 = 2.5 muM). Inhibits de novo pyrimidine synthesis in human T cells in vitro; also inhibits lymphocyte proliferation. Exhibits efficacy in several animal models of autoimmune disease, arthritis and graft rejection. Active metabolite, teriflunomide (A77 1726, Cat. No. 5069), also available. Tocris Bioscience 2228
      Leflunomide(SU101; HWA486; RS-34821) is a disease-modifying antirheumatic drug, which is a pyrimidine synthesis inhibitor. MedChem Express
      Leflunomide(SU101; HWA486; RS-34821) is a disease-modifying antirheumatic drug, which is a pyrimidine synthesis inhibitor.; IC50 Value: ; Target: pyrimidine synthesis; Leflunomide is a pyrimidine synthesis inhibitor belonging to the DMARD (disease-modifying antirheumatic drug) class of drugs. MedChem Express HY-B0083
      Other Dehydrogenases Tocris Bioscience 2228
      Others MedChem Express HY-B0083
      Protein-tyrosine kinase 2;AhR;DHODH TargetMol T1159

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

Density: 1.4±0.1 g/cm3
Boiling Point: 289.3±40.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.6 mmHg at 25°C
Enthalpy of Vaporization: 52.9±3.0 kJ/mol
Flash Point: 128.8±27.3 °C
Index of Refraction: 1.541
Molar Refractivity: 61.0±0.3 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 1.95
ACD/LogD (pH 5.5): 2.20
ACD/BCF (pH 5.5): 27.82
ACD/KOC (pH 5.5): 376.21
ACD/LogD (pH 7.4): 2.20
ACD/BCF (pH 7.4): 27.81
ACD/KOC (pH 7.4): 376.18
Polar Surface Area: 55 Å2
Polarizability: 24.2±0.5 10-24cm3
Surface Tension: 40.6±3.0 dyne/cm
Molar Volume: 194.1±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) =  2.43

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  378.79  (Adapted Stein & Brown method)
    Melting Pt (deg C):  155.71  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.25E-006  (Modified Grain method)
    Subcooled liquid VP: 2.71E-005 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):  152.7
       log Kow used: 2.43 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  23.356 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.23E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.910E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.43  (KowWin est)
  Log Kaw used:  -8.299  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.729
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3633
   Biowin2 (Non-Linear Model)     :   0.0381
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9600  (months      )
   Biowin4 (Primary Survey Model) :   3.3204  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1696
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5807
 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):  0.00361 Pa (2.71E-005 mm Hg)
  Log Koa (Koawin est  ): 10.729
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00083 
       Octanol/air (Koa) model:  0.0132 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0291 
       Mackay model           :  0.0623 
       Octanol/air (Koa) model:  0.513 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   7.3337 E-12 cm3/molecule-sec
      Half-Life =     1.458 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    17.502 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.0457 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2323
      Log Koc:  3.366 

 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 = 1.172 (BCF = 14.88)
       log Kow used: 2.43 (estimated)

 Volatilization from Water:
    Henry LC:  1.23E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.825E+006  hours   (3.26E+005 days)
    Half-Life from Model Lake : 8.536E+007  hours   (3.557E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               2.91  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.81  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       0.000753        35           1000       
   Water     15.6            1.44e+003    1000       
   Soil      84.3            2.88e+003    1000       
   Sediment  0.117           1.3e+004     0          
     Persistence Time: 2.31e+003 hr




                    

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