ChemSpider 2D Image | Eltrombopag | C25H22N4O4

Eltrombopag

  • Molecular FormulaC25H22N4O4
  • Average mass442.467 Da
  • Monoisotopic mass442.164093 Da
  • ChemSpider ID19879943
  • Double-bond stereo - Double-bond stereo


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

(Z)-Eltrombopag
[1,1'-Biphenyl]-3-carboxylic acid, 3'-[(2Z)-2-[1-(3,4-dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4H-pyrazol-4-ylidene]hydrazinyl]-2'-hydroxy- [ACD/Index Name]
3'-{(2Z)-2-[1-(3,4-Dimethylphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-yliden]hydrazino}-2'-hydroxy-3-biphenylcarbonsäure [German] [ACD/IUPAC Name]
3'-{(2Z)-2-[1-(3,4-Dimethylphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene]hydrazino}-2'-hydroxy-3-biphenylcarboxylic acid [ACD/IUPAC Name]
496775-61-2 [RN]
8655
Acide 3'-{(2Z)-2-[1-(3,4-diméthylphényl)-3-méthyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidène]hydrazino}-2'-hydroxy-3-biphénylcarboxylique [French] [ACD/IUPAC Name]
eltrombopag [Spanish] [INN]
eltrombopag [French] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

SB-497115 [DBID]
SB-497115-GR [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1872
      B02BX05 Wikidata Q411588
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1872
      IRRITANT Matrix Scientific 090195
      no pictogram Axon Medchem 1872
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1872
      Warning Axon Medchem 1872
    • Chemical Class:

      A hydrazine in which each nitrogen atom is substituted, one by a 3'-carboxy-2-hydroxy[1,1'-biphenyl]-3-yl group and the other by a 1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1,5-dihydro-4<element>H</elemen t>-pyrazol-4-ylidene group. A small molecule agonist of the c-mpl (TpoR) receptor (the physiological target of the hormone thrombopoietin), it has been developed as a medication for conditions that l ead to thrombocytopenia (abnormally low platelet counts). ChEBI CHEBI:85010
    • Bio Activity:

      Eltrombopag(SB-497115) is a new, orally active thrombopoietin-receptor (c-mpl) agonist that stimulates thrombopoiesis. MedChem Express
      Eltrombopag(SB-497115) is a new, orally active thrombopoietin-receptor (c-mpl) agonist that stimulates thrombopoiesis.; IC50 Value: 0.27 uM (EC50 in murine BAF3 cells) [1]; Target: thrombopoietin-receptor (c-mpl); Potential advantages of eltrombopag may include a sustained platelet response and a good tolerability profile.; in vitro: Eltrombopag demonstrated a half maximal effective concentration (EC50) of 0.27 uM in murine BAF3 cells transfected with the luciferase reporter gene under direction of the STAT-activated IRF-1 promoter and human TpoR (BAF3/IRF-1/hTpoR) [1]. MedChem Express HY-15306
      Eltrombopag(SB-497115) is a new, orally active thrombopoietin-receptor (c-mpl) agonist that stimulates thrombopoiesis.;IC50 Value: 0.27 uM (EC50 in murine BAF3 cells) [1];Target: thrombopoietin-receptor (c-mpl)Potential advantages of eltrombopag may include a sustained platelet response and a good tolerability profile.;In vitro: Eltrombopag demonstrated a half maximal effective concentration (EC50) of 0.27 uM in murine BAF3 cells transfected with the luciferase reporter gene under direction of the STAT-activated IRF-1 promoter and human TpoR (BAF3/IRF-1/hTpoR) [1]. Eltrombopag stimulates the growth of TPO-dependent cell lines via JAK2 and STAT signaling pathways and stimulates isolated human CD34+ cells to become megakaryocytes and produce platelets [2].;In vivo: Twelve weeks of antiviral therapy, with concurrent receipt of eltrombopag or placebo, were completed by 36%, 53%, and 65% of patients receiving 30 mg, 50 mg, and 75 mg of eltrombopag, respectively, and by 6% of patients MedChem Express HY-15306
      Others MedChem Express HY-15306
      Thrombopoietin Receptor MedChem Express HY-15306

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

Density: 1.3±0.1 g/cm3
Boiling Point: 656.8±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 101.6±3.0 kJ/mol
Flash Point: 351.0±34.3 °C
Index of Refraction: 1.667
Molar Refractivity: 123.5±0.5 cm3
#H bond acceptors: 8
#H bond donors: 3
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 3.70
ACD/LogD (pH 5.5): 2.48
ACD/BCF (pH 5.5): 20.08
ACD/KOC (pH 5.5): 114.19
ACD/LogD (pH 7.4): 0.64
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.66
Polar Surface Area: 115 Å2
Polarizability: 49.0±0.5 10-24cm3
Surface Tension: 52.5±7.0 dyne/cm
Molar Volume: 332.0±7.0 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) =  6.15

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  690.80  (Adapted Stein & Brown method)
    Melting Pt (deg C):  301.72  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.17E-017  (Modified Grain method)
    Subcooled liquid VP: 1.45E-014 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):  0.03543
       log Kow used: 6.15 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.023749 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Hydrazines-acid
       Phenols-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.44E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.923E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.15  (KowWin est)
  Log Kaw used:  -18.001  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  24.151
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9389
   Biowin2 (Non-Linear Model)     :   0.7704
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2159  (months      )
   Biowin4 (Primary Survey Model) :   3.1197  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0025
   Biowin6 (MITI Non-Linear Model):   0.0042
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5950
 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):  1.93E-012 Pa (1.45E-014 mm Hg)
  Log Koa (Koawin est  ): 24.151
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.55E+006 
       Octanol/air (Koa) model:  3.48E+011 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  92.7766 E-12 cm3/molecule-sec
      Half-Life =     0.115 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.383 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4.594E+005
      Log Koc:  5.662 

 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 = 1.750 (BCF = 56.23)
       log Kow used: 6.15 (estimated)

 Volatilization from Water:
    Henry LC:  2.44E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.047E+016  hours   (2.103E+015 days)
    Half-Life from Model Lake : 5.506E+017  hours   (2.294E+016 days)

 Removal In Wastewater Treatment:
    Total removal:              92.70  percent
    Total biodegradation:        0.77  percent
    Total sludge adsorption:    91.93  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       8.6e-006        2.77         1000       
   Water     2.08            1.44e+003    1000       
   Soil      48.2            2.88e+003    1000       
   Sediment  49.7            1.3e+004     0          
     Persistence Time: 5.46e+003 hr




                    

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