ChemSpider 2D Image | Cladribine | C10H12ClN5O3

Cladribine

  • Molecular FormulaC10H12ClN5O3
  • Average mass285.687 Da
  • Monoisotopic mass285.062866 Da
  • ChemSpider ID19105
  • defined stereocentres - 3 of 3 defined stereocentres


More details:



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

(2R,3S,5R)-5-(6-Amino-2-chlor-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol
(2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol
(2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-2-(hydroxyméthyl)tétrahydrofuran-3-ol
2-Chlor-2'-desoxyadenosin [German] [ACD/IUPAC Name]
2-Chloro-2'-deoxyadenosine
2-Chloro-2'-deoxy-adenosine
2-CHLORO-2'-DEOXYADENOSINE [ACD/IUPAC Name]
2-Chloro-2'-deoxy-b-adenosine
2-Chloro-2'-deoxy-β-adenosine
2-Chloro-2'-désoxyadénosine [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

47M74X9YT5 [DBID]
AIDS022294 [DBID]
AIDS-022294 [DBID]
BRN 0624220 [DBID]
D01370 [DBID]
MLS000028377 [DBID]
MLS000028484 [DBID]
NSC 105014 [DBID]
NSC 105014-F [DBID]
NSC105014 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 075196
      L01BB04 Wikidata Q414030
    • Target Organs:

      DNA/RNA Synthesis inhibitor TargetMol T2558
    • Chemical Class:

      2'-Deoxyadenosine in which the hydrogen at position 2 on the purine ring has been substituted by chlorine. It inhibits the synthesis and repair of DNA, particularly in lymphocytes and monocytes, and is used as an antimetabolite antineoplastic drug for the treatment of lymphoid malignancies including hairy-cell leukaemia and chronic lymphocytic leukaemia. ChEBI CHEBI:567361
    • Therapeutical Effect:

      Antineoplastic Agents,Immunosuppressive Agents Sean Ekins
    • Bio Activity:

      Adenosine Deaminase MedChem Express HY-13599
      Adenosine deaminase TargetMol T2558
      Adenosine deaminase (ADA)-resistant analog of deoxyadenosine. Exhibits anti-leukemic activity; Inhibits cell growth of lymphoid and myeloid neoplasm (IC50 = 20 - 87 nM). Pro-apoptotic; induces DNA dou ble-strand breaks. Also inhibits ribonuclease reductase (IC50 = 0.11 - 0.28 ?M). Displays activity in vitro and in vivo. Orally bioavailable. Tocris Bioscience 5292
      Adenosine deaminase (ADA)-resistant analog of deoxyadenosine. Exhibits anti-leukemic activity; Inhibits cell growth of lymphoid and myeloid neoplasm (IC50 = 20 - 87 nM). Pro-apoptotic; induces DNA double-strand breaks. Also inhibits ribonuclease reductase (IC50 = 0.11 - 0.28 ?M). Displays activity in vitro and in vivo. Orally bioavailable. Tocris Bioscience 5292
      Adenosine deaminase (ADA)-resistant analog of deoxyadenosine. Exhibits anti-leukemic activity; Inhibits cell growth of lymphoid and myeloid neoplasm (IC50 = 20 - 87 nM). Pro-apoptotic; induces DNA double-strand breaks. Also inhibits ribonuclease reductase (IC50 = 0.11 - 0.28 muM). Displays activity in vitro and in vivo. Orally bioavailable. Tocris Bioscience 5292
      Apoptosis Tocris Bioscience 5292
      Apoptosis Inducers Tocris Bioscience 5292
      Cell Biology Tocris Bioscience 5292
      Cladribine is an adenosine deaminase inhibitor used to treat hairy cell leukemia and multiple sclerosis. MedChem Express http://www.medchemexpress.com/cladribine.html, HY-13599
      Cladribine is an adenosine deaminase inhibitor used to treat hairy cell leukemia and multiple sclerosis. ;Target: Adenosine DeaminaseCladribine possesses concentration-dependent apoptosis-inducing potential in the HSB2 cells. Cladribine inhibits growth of primary mast cell (MC) and the MC line HMC-1 in a dose-dependent manner, with lower IC50 values recorded in HMC-1.2 cells harboring KIT D816V compared to HMC-1.1 cells lacking KIT D816V. Cladribine (0.7-3.5 mM) and/or diltiazem (2.4 mM), is injected intraperitoneally into adult zebrafish and red blood cell (RBC) lysates are assayed by HPLC for levels of purine nucleotides (e.g. ATP), potential biomarkers of cardiovascular health. Diltiazem increased RBC ATP concentrations, which are inhibited by co-injection of cladribine. MedChem Express HY-13599
      Deoxyadenosine analog; pro-apoptotic Tocris Bioscience 5292
      DNA Damage/DNA Repair TargetMol T2558
      Metabolism/Protease MedChem Express HY-13599
      Metabolism/Protease; MedChem Express HY-13599

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

Density: 2.0±0.1 g/cm3
Boiling Point: 547.6±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 87.0±3.0 kJ/mol
Flash Point: 285.0±32.9 °C
Index of Refraction: 1.871
Molar Refractivity: 63.7±0.5 cm3
#H bond acceptors: 8
#H bond donors: 4
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 0.02
ACD/LogD (pH 5.5): 0.01
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 24.17
ACD/LogD (pH 7.4): 0.01
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 24.17
Polar Surface Area: 119 Å2
Polarizability: 25.3±0.5 10-24cm3
Surface Tension: 93.5±7.0 dyne/cm
Molar Volume: 140.2±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) =  -0.07
    Log Kow (Exper. database match) =  0.02
       Exper. Ref:  BioByte (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  519.69  (Adapted Stein & Brown method)
    Melting Pt (deg C):  221.79  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.11E-013  (Modified Grain method)
    Subcooled liquid VP: 1.42E-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):  699.8
       log Kow used: 0.02 (expkow database)
       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 :   2.25E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.963E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.02  (exp database)
  Log Kaw used:  -19.036  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.056
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1655
   Biowin2 (Non-Linear Model)     :   0.0021
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5375  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4110  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1491
   Biowin6 (MITI Non-Linear Model):   0.0076
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0932
 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):  1.89E-009 Pa (1.42E-011 mm Hg)
  Log Koa (Koawin est  ): 19.056
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.58E+003 
       Octanol/air (Koa) model:  2.79E+006 
   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 = 187.7183 E-12 cm3/molecule-sec
      Half-Life =     0.057 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.684 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: 0.02 (expkow database)

 Volatilization from Water:
    Henry LC:  2.25E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.398E+017  hours   (1.833E+016 days)
    Half-Life from Model Lake : 4.798E+018  hours   (1.999E+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       2.87e-009       1.37         1000       
   Water     45.7            900          1000       
   Soil      54.2            1.8e+003     1000       
   Sediment  0.0887          8.1e+003     0          
     Persistence Time: 982 hr




                    

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