ChemSpider 2D Image | Axitinib | C22H18N4OS

Axitinib

  • Molecular FormulaC22H18N4OS
  • Average mass386.470 Da
  • Monoisotopic mass386.120117 Da
  • ChemSpider ID4953153
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

319460-85-0 [RN]
8720
axitinib [Spanish] [INN]
axitinib [French] [INN]
axitinibum [Latin] [INN]
Benzamide, N-methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1H-indazol-6-yl]thio]-
Benzamide, N-methyl-2-[[3-[(E)-2-(2-pyridinyl)ethenyl]-1H-indazol-6-yl]thio]- [ACD/Index Name]
C9LVQ0YUXG
N-Methyl-2-({3-[(E)-2-(2-pyridinyl)vinyl]-1H-indazol-6-yl}sulfanyl)benzamid [German] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AG-13736 [DBID]
AG 013736 [DBID]
AG-013736 [DBID]
D03218 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1414
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1414
      IRRITANT Matrix Scientific 095403
      L01XE17 Wikidata Q4830631
      no pictogram Axon Medchem 1414
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1414
      Sold for research purposes under agreement from Pfizer Inc. Tocris Bioscience 4350
      Warning Axon Medchem 1414
    • Target Organs:

      c-Kit inhibitor; PDGFR inhibitor; VEGFR inhibitor TargetMol T1452
    • Chemical Class:

      An indazole substituted at position 3 by a 2-(pyridin-2-yl)vinyl group and at position 6 by a 2-(<element>N</element>-methylaminocarboxy)phenylsulfanyl group. Used for the treatment of advanced renal cell carcinoma after failure of a first line systemic treatment. ChEBI CHEBI:66910
    • Bio Activity:

      Axitinib(AG013736) blocked phosphorylation of VEGFR-2 and VEGFR-3 with average IC50s of 0.2 and 0.1 to 0.3 nM.; IC50 value:; Target: VEGFR2/3 MedChem Express HY-10065
      Axitinib(AG013736) blocked phosphorylation of VEGFR-2 and VEGFR-3 with average IC50s of 0.2 and 0.1 to 0.3 nM.;IC50 value:;Target: VEGFR2/3 MedChem Express HY-10065
      c-Kit;PDGFR??;VEGFR1, VEGFR2, VEGFR3 TargetMol T1452
      Enzyme-Linked Receptors Tocris Bioscience 4350
      Potent inhibitor of VEGFR-2, -3, and -1 (IC50 values are 0.2, 0.1-0.3, and 1.2 nM respectively). Exhibits minimal activity against a panel of ~100 protein kinase. Inhibits angiogenesis and vascular pe rmeability. Also a high affinity BCR-ABL1 (T315I) inhibitor (Ki = 149 pM for autophosphorylated ABL1 (T315I)). Blocks proliferation of Ba/F3 cells expressing BCR-ABL1 (T315I). Orally available. Tocris Bioscience 4350
      Potent inhibitor of VEGFR-2, -3, and -1 (IC50 values are 0.2, 0.1-0.3, and 1.2 nM respectively). Exhibits minimal activity against a panel of ~100 protein kinase. Inhibits angiogenesis and vascular permeability. Also a high affinity BCR-ABL1 (T315I) inhibitor (Ki = 149 pM for autophosphorylated ABL1 (T315I)). Blocks proliferation of Ba/F3 cells expressing BCR-ABL1 (T315I). Orally available. Tocris Bioscience 4350
      Potent VEGFR-1, -2 and -3 inhibitor Tocris Bioscience 4350
      Protein Tyrosine Kinase/RTK MedChem Express HY-10065
      Protein Tyrosine Kinase/RTK; MedChem Express HY-10065
      Receptor Tyrosine Kinases (RTKs) Tocris Bioscience 4350
      Tyrosine Kinase/Adaptors TargetMol T1452
      VEGFR Tocris Bioscience 4350
      VEGFR MedChem Express HY-10065

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

Density: 1.4±0.1 g/cm3
Boiling Point: 668.9±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.0 mmHg at 25°C
Enthalpy of Vaporization: 98.3±3.0 kJ/mol
Flash Point: 358.3±31.5 °C
Index of Refraction: 1.728
Molar Refractivity: 113.5±0.4 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 4.15
ACD/LogD (pH 5.5): 3.63
ACD/BCF (pH 5.5): 334.58
ACD/KOC (pH 5.5): 2203.52
ACD/LogD (pH 7.4): 3.65
ACD/BCF (pH 7.4): 349.68
ACD/KOC (pH 7.4): 2303.01
Polar Surface Area: 96 Å2
Polarizability: 45.0±0.5 10-24cm3
Surface Tension: 75.2±5.0 dyne/cm
Molar Volume: 284.8±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) =  4.09

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  648.54  (Adapted Stein & Brown method)
    Melting Pt (deg C):  281.99  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.62E-015  (Modified Grain method)
    Subcooled liquid VP: 3.91E-012 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):  1.203
       log Kow used: 4.09 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  22.188 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.70E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.376E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.09  (KowWin est)
  Log Kaw used:  -17.633  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  21.723
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6191
   Biowin2 (Non-Linear Model)     :   0.1937
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0767  (months      )
   Biowin4 (Primary Survey Model) :   3.4768  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2413
   Biowin6 (MITI Non-Linear Model):   0.0011
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3671
 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):  5.21E-010 Pa (3.91E-012 mm Hg)
  Log Koa (Koawin est  ): 21.723
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.75E+003 
       Octanol/air (Koa) model:  1.3E+009 
   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 = 141.6125 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 149.2125 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.906 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.860 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    12.599999 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    25.199999 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     2.183 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     1.091 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   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    :  4.373E+005
      Log Koc:  5.641 

 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 = 2.446 (BCF = 279.3)
       log Kow used: 4.09 (estimated)

 Volatilization from Water:
    Henry LC:  5.7E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.019E+016  hours   (8.414E+014 days)
    Half-Life from Model Lake : 2.203E+017  hours   (9.179E+015 days)

 Removal In Wastewater Treatment:
    Total removal:              34.34  percent
    Total biodegradation:        0.35  percent
    Total sludge adsorption:    33.98  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       1.21e-007       0.99         1000       
   Water     8.37            1.44e+003    1000       
   Soil      88.5            2.88e+003    1000       
   Sediment  3.13            1.3e+004     0          
     Persistence Time: 2.95e+003 hr




                    

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