ChemSpider 2D Image | Deferasirox | C21H15N3O4

Deferasirox

  • Molecular FormulaC21H15N3O4
  • Average mass373.362 Da
  • Monoisotopic mass373.106262 Da
  • ChemSpider ID10770206

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201530-41-8 [RN]
4-[3,5-Bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzoesäure [German] [ACD/IUPAC Name]
4-[3,5-Bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzoic acid [ACD/IUPAC Name]
4-[3,5-Bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzolcarbonsäure [German]
8193
Acide 4-[3,5-bis(2-hydroxyphényl)-1H-1,2,4-triazol-1-yl]benzoïque [French] [ACD/IUPAC Name]
Benzoic acid, 4-[3,5-bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]- [ACD/Index Name]
deferasiroxum [Latin] [INN]
Exjade [Trade name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

ICL670A [DBID]
ICL 670 [DBID]
ICL 670A [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      V03AC03 Wikidata Q5251502
    • Chemical Class:

      A member of the class of triazoles, deferasirox is 1,2,4-triazole substituted by a 4-carboxyphenyl group at position 1 and by 2-hydroxyphenyl groups at positions 3 and 5. An orally active iron chelato r, it is used to manage chronic iron overload in patients receiving long-term blood transfusions. ChEBI CHEBI:49005
    • Drug Status:

      approved BIONET-Key Organics KE-0220
    • Bio Activity:

      Deferasirox (marketed as Exjade) is a rationally-designed oral iron chelator. MedChem Express http://www.medchemexpress.com/BIBR-1532.html, HY-17359
      Deferasirox (marketed as Exjade) is a rationally-designed oral iron chelator. ;IC50 value:;Target: Deferasirox's main use is to reduce chronic iron overload in patients who are receiving long-term blood transfusions for conditions such as beta-thalassemia and other chronic anemias. Deferasirox is the first oral medication approved in the USA for this purpose. The half-life of deferasirox is between 8 and 16 hours allowing once a day dosing. Two molecules of deferasirox are capable of binding to 1 atom of iron which are subsequently eliminated by fecal excretion. Its low molecular weight and high lipophilicity allows the drug to be taken orally unlike desferoxamine which has to be administered by IV route (intravenous infusion). Together with deferiprone, deferasirox seems to be capable of removing iron from cells (cardiac myocytes and hepatocytes) as well as removing iron from the blood. (From Wikipedia) MedChem Express HY-17359
      Others MedChem Express HY-17359

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

Density: 1.4±0.1 g/cm3
Boiling Point: 672.1±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 103.7±3.0 kJ/mol
Flash Point: 360.3±34.3 °C
Index of Refraction: 1.699
Molar Refractivity: 102.6±0.5 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 1
ACD/LogP: 6.43
ACD/LogD (pH 5.5): 2.29
ACD/BCF (pH 5.5): 10.98
ACD/KOC (pH 5.5): 53.34
ACD/LogD (pH 7.4): 0.83
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.85
Polar Surface Area: 108 Å2
Polarizability: 40.7±0.5 10-24cm3
Surface Tension: 60.8±7.0 dyne/cm
Molar Volume: 265.8±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) =  3.45

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  627.84  (Adapted Stein & Brown method)
    Melting Pt (deg C):  272.32  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.63E-016  (Modified Grain method)
    Subcooled liquid VP: 8.6E-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):  19.16
       log Kow used: 3.45 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  53.872 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.14E-024  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.179E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.45  (KowWin est)
  Log Kaw used:  -21.535  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  24.985
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9783
   Biowin2 (Non-Linear Model)     :   0.8751
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5747  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3962  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2054
   Biowin6 (MITI Non-Linear Model):   0.0326
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1179
 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):  1.15E-011 Pa (8.6E-014 mm Hg)
  Log Koa (Koawin est  ): 24.985
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.62E+005 
       Octanol/air (Koa) model:  2.37E+012 
   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 =  49.7721 E-12 cm3/molecule-sec
      Half-Life =     0.215 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.579 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    :  1.182E+006
      Log Koc:  6.073 

 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: 3.45 (estimated)

 Volatilization from Water:
    Henry LC:  7.14E-024 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.584E+020  hours   (6.602E+018 days)
    Half-Life from Model Lake : 1.729E+021  hours   (7.202E+019 days)

 Removal In Wastewater Treatment:
    Total removal:              11.94  percent
    Total biodegradation:        0.17  percent
    Total sludge adsorption:    11.77  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       1.05e-009       5.16         1000       
   Water     11.7            900          1000       
   Soil      87.6            1.8e+003     1000       
   Sediment  0.752           8.1e+003     0          
     Persistence Time: 1.84e+003 hr




                    

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