ChemSpider 2D Image | Teriflunomide | C12H9F3N2O2

Teriflunomide

  • Molecular FormulaC12H9F3N2O2
  • Average mass270.207 Da
  • Monoisotopic mass270.061615 Da
  • ChemSpider ID16737143
  • Double-bond stereo - Double-bond stereo


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(2Z)-2-Cyan-3-hydroxy-N-[4-(trifluormethyl)phenyl]-2-butenamid [German] [ACD/IUPAC Name]
(2Z)-2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-2-butenamide [ACD/IUPAC Name]
(2Z)-2-Cyano-3-hydroxy-N-[4-(trifluorométhyl)phényl]-2-buténamide [French] [ACD/IUPAC Name]
(2Z)-2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
(Z)-2-Cyano-3-hydroxy-but-2-enoic acid (4-trifluoromethyl-phenyl)-amide
(Z)-2-Cyano-a',a',a'-trifluoro-3-hydroxy-p-crotonotoluidide
163451-81-8 [RN]
2-Butenamide, 2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-, (2Z)- [ACD/Index Name]
A77 1726
Aubagio
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

HMR1726 [DBID]
A 771726 [DBID]
A-771726 [DBID]
HMR-1726 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Bio Activity:

      Dihydroorotate dehydrogenase inhibitor Tocris Bioscience 5069
      Inhibitor of dihydroorotate dehydrogenase (Kd = 12 nM; Ki = 179 nM). Inhibits proliferation of mitogen- or cytokine-stimulated lymphoid cells in vitro by inhibiting cell cycle progression from G1 to S . Imunosuppressive agent. Active metabolite of leflunomide (Cat. No. 2228). Tocris Bioscience 5069
      Teriflunomide (A77 1726), the active metabolite of an approved antirheumatic drug Leflunomide, is an emerging oral therapy for multiple sclerosis (MS). MedChem Express http://www.medchemexpress.com/Frentizole.html
      Teriflunomide (A77 1726), the active metabolite of an approved antirheumatic drug Leflunomide, is an emerging oral therapy for multiple sclerosis (MS). ;IC50 value:;Target: ;Teriflunomide has demonstrated anti-inflammatory, antiproliferative and immunosuppressive effects. Teriflunomide is an immunomodulator with a unique mechanism of action. Although the mechanism of action for Teriflunomide is not fully understood, research supports that Teriflunomide inhibits the proliferation of stimulated T and B lymphocytes in the periphery thought to be responsible for the damaging inflammatory process in MS, while generally maintaining normal immune function. Teriflunomide selectively and reversibly inhibits DHODH, a key enzyme in de novo pyrimidine synthesis required by rapidly dividing lymphocytes. Through this effect, it limits the expansion of stimulated T- and B-cells in the periphery and diminishes the numbers of activated T- and B-cells available to migrate into the central nervous sy MedChem Express HY-15405

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

Density: 1.4±0.1 g/cm3
Boiling Point: 410.8±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 69.9±3.0 kJ/mol
Flash Point: 202.3±28.7 °C
Index of Refraction: 1.552
Molar Refractivity: 60.6±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 2.51
ACD/LogD (pH 5.5): 1.38
ACD/BCF (pH 5.5): 4.59
ACD/KOC (pH 5.5): 66.87
ACD/LogD (pH 7.4): -0.37
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.16
Polar Surface Area: 73 Å2
Polarizability: 24.0±0.5 10-24cm3
Surface Tension: 45.4±3.0 dyne/cm
Molar Volume: 189.7±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) =  2.25

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  439.95  (Adapted Stein & Brown method)
    Melting Pt (deg C):  174.88  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.4E-010  (Modified Grain method)
    Subcooled liquid VP: 1.22E-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):  118.1
       log Kow used: 2.25 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  331.18 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Allylic/Vinyl Nitriles
       Acrylamides
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.87E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.024E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.25  (KowWin est)
  Log Kaw used:  -11.931  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.181
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7744
   Biowin2 (Non-Linear Model)     :   0.8760
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1125  (months      )
   Biowin4 (Primary Survey Model) :   3.4532  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3531
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0603
 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):  1.63E-006 Pa (1.22E-008 mm Hg)
  Log Koa (Koawin est  ): 14.181
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.84 
       Octanol/air (Koa) model:  37.2 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.985 
       Mackay model           :  0.993 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  15.0103 E-12 cm3/molecule-sec
      Half-Life =     0.713 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     8.551 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.056875 E-17 cm3/molecule-sec
      Half-Life =    20.149 Days (at 7E11 mol/cm3)
   Fraction sorbed to airborne particulates (phi): 0.989 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  28.01
      Log Koc:  1.447 

 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 = 1.034 (BCF = 10.82)
       log Kow used: 2.25 (estimated)

 Volatilization from Water:
    Henry LC:  2.87E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.353E+010  hours   (1.397E+009 days)
    Half-Life from Model Lake : 3.658E+011  hours   (1.524E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               2.55  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.46  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       1.61e-005       16.5         1000       
   Water     18.3            1.44e+003    1000       
   Soil      81.6            2.88e+003    1000       
   Sediment  0.102           1.3e+004     0          
     Persistence Time: 2.14e+003 hr




                    

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