ChemSpider 2D Image | Clofarabine | C10H11ClFN5O3

Clofarabine

  • Molecular FormulaC10H11ClFN5O3
  • Average mass303.677 Da
  • Monoisotopic mass303.053436 Da
  • ChemSpider ID106472
  • defined stereocentres - 4 of 4 defined stereocentres


More details:



Featured data source



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

(2R,3R,4S,5R)-5-(6-Amino-2-chlor-9H-purin-9-yl)-4-fluor-2-(hydroxymethyl)tetrahydrofuran-3-ol
(2R,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol
(2R,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxyméthyl)tétrahydrofuran-3-ol
123318-82-1 [RN]
2-Chlor-9-(2-desoxy-2-fluor-β-D-arabinofuranosyl)-9H-purin-6-amin [German] [ACD/IUPAC Name]
2-Chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purin-6-amine [ACD/IUPAC Name]
2-Chloro-9-(2-désoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purin-6-amine [French] [ACD/IUPAC Name]
762RDY0Y2H
8422
9H-Purin-6-amine, 2-chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)- [ACD/Index Name]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      Danger Biosynth Q-101871
      GHS06 Biosynth Q-101871
      H301 Biosynth Q-101871
      L01BB06 Wikidata Q5134875
      P264; P301+P310 Biosynth Q-101871
    • Target Organs:

      RNA Synthesis TargetMol T0297
    • Chemical Class:

      A purine nucleoside analogue consisting of a 6-amino-2-chloropurin-9-yl group attached to the 1<stereo>beta</stereo> position of 2'-deoxy-2'-fluoro-<stereo>D</stereo>-arabinofuranose. It is metabolize d intracellularly to the active 5'-triphosphate metabolite, which inhibits DNA synthesisis and so stops the growth of cancer cells. Clofarabine is used as an antimetabolite antineoplastic agent in the treatment of relapsed or refractory acute lymphoblastic leukaemia. ChEBI CHEBI:681569
    • Bio Activity:

      . Zerenex Molecular [ZBioX-0114]
      Cell Cycle/DNA Damage MedChem Express HY-A0005
      Cell Cycle/DNA Damage; MedChem Express HY-A0005
      Clofarabine(Clolar; Clofarex) inhibits the enzymatic activities of ribonucleotide reductase (IC50 = 65 nM) and DNA polymerase. MedChem Express
      Clofarabine(Clolar; Clofarex) inhibits the enzymatic activities of ribonucleotide reductase (IC50 = 65 nM) and DNA polymerase.; IC50 Value: 65 nM; Target: ; in vitro: Clofarabine is a second generation purine nucleoside analog with antineoplastic activity. MedChem Express HY-A0005
      Clofarabine(Clolar; Clofarex) inhibits the enzymatic activities of ribonucleotide reductase (IC50 = 65 nM) and DNA polymerase.;IC50 Value: 65 nM;Target: ;In vitro: Clofarabine is a second generation purine nucleoside analog with antineoplastic activity. It is phosphorylated intracellularly, which inhibits the enzymatic activities of ribonucleotide reductase (IC50 = 65 nM) and DNA polymerase, resulting in inhibition of DNA repair and synthesis of DNA and RNA. This nucleoside analog also disrupts mitochondrial function and membrane integrity, resulting in the release of pre-apoptotic factors, including cytochrome C and apoptotic-inducing factor, which activate apoptosis.;In vivo: Clofarabine is used for treating relapsed or refractory acute lymphoblastic leukaemia (ALL) in children, after at least two other types of treatment have failed. MedChem Express HY-A0005
      Deoxycytidine kinase (dCK) substrate Tocris Bioscience 2600
      Deoxycytidine kinase (dCK) substrate. Phosphorylated to form clofarabine triphosphate, which competes with dATP for DNA polymerase-? and -? and potently inhibits ribonucleotide reductase (IC50 = 65 nM ). Induces apoptosis by directly altering mitochondrial transmembrane potential. Demonstrates growth inhibition and cytotoxic activity in a variety of leukemias and solid tumors. Tocris Bioscience 2600
      Deoxycytidine kinase (dCK) substrate. Phosphorylated to form clofarabine triphosphate, which competes with dATP for DNA polymerase-? and -? and potently inhibits ribonucleotide reductase (IC50 = 65 nM). Induces apoptosis by directly altering mitochondrial transmembrane potential. Demonstrates growth inhibition and cytotoxic activity in a variety of leukemias and solid tumors. Tocris Bioscience 2600
      Deoxycytidine kinase (dCK) substrate. Phosphorylated to form clofarabine triphosphate, which competes with dATP for DNA polymerase-alpha and -epsilon and potently inhibits ribonucleotide reductase (IC50 = 65 nM). Induces apoptosis by directly altering mitochondrial transmembrane potential. Demonstrates growth inhibition and cytotoxic activity in a variety of leukemias and solid tumors. Tocris Bioscience 2600
      DNA Damage/DNA Repair TargetMol T0297
      Enzymes Tocris Bioscience 2600
      Kinases Tocris Bioscience 2600
      Nucleoside antimetabolite/analog MedChem Express HY-A0005
      Other Kinases Tocris Bioscience 2600
      Ribonucleotide reductase TargetMol T0297

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

Density: 2.1±0.1 g/cm3
Boiling Point: 599.5±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 93.9±3.0 kJ/mol
Flash Point: 316.4±32.9 °C
Index of Refraction: 1.844
Molar Refractivity: 63.6±0.5 cm3
#H bond acceptors: 8
#H bond donors: 4
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 0.24
ACD/LogD (pH 5.5): -0.17
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 19.28
ACD/LogD (pH 7.4): -0.17
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 19.28
Polar Surface Area: 119 Å2
Polarizability: 25.2±0.5 10-24cm3
Surface Tension: 86.3±7.0 dyne/cm
Molar Volume: 143.1±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) =  -0.20

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  517.46  (Adapted Stein & Brown method)
    Melting Pt (deg C):  220.75  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.35E-013  (Modified Grain method)
    Subcooled liquid VP: 1.67E-011 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):  849.5
       log Kow used: -0.20 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aromatic Amines
       Imidazoles

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.49E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.350E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.20  (KowWin est)
  Log Kaw used:  -18.736  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.536
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1569
   Biowin2 (Non-Linear Model)     :   0.0016
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4978  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3850  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1057
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2526
 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):  2.23E-009 Pa (1.67E-011 mm Hg)
  Log Koa (Koawin est  ): 18.536
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.35E+003 
       Octanol/air (Koa) model:  8.43E+005 
   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 = 163.7637 E-12 cm3/molecule-sec
      Half-Life =     0.065 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.784 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  10
      Log Koc:  1.000 

 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: -0.20 (estimated)

 Volatilization from Water:
    Henry LC:  4.49E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.272E+017  hours   (9.468E+015 days)
    Half-Life from Model Lake : 2.479E+018  hours   (1.033E+017 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       4.84e-009       1.57         1000       
   Water     46              900          1000       
   Soil      53.9            1.8e+003     1000       
   Sediment  0.0889          8.1e+003     0          
     Persistence Time: 978 hr




                    

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