ChemSpider 2D Image | Clevudine | C10H13FN2O5

Clevudine

  • Molecular FormulaC10H13FN2O5
  • Average mass260.219 Da
  • Monoisotopic mass260.080841 Da
  • ChemSpider ID65894
  • defined stereocentres - 4 of 4 defined stereocentres


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1-(2-Deoxy-2-fluoro-b-L-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione
1-(2-Deoxy-2-fluoro-β-L-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione [ACD/IUPAC Name]
1-(2-Deoxy-2-fluoro-β-L-arabinofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione
1-(2-Désoxy-2-fluoro-β-L-arabinofuranosyl)-5-méthyl-2,4(1H,3H)-pyrimidinedione [French] [ACD/IUPAC Name]
1-(2-Desoxy-2-fluor-β-L-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidindion [German] [ACD/IUPAC Name]
163252-36-6 [RN]
2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-methyl- [ACD/Index Name]
2'-Fluoro-5-methyl-b-L-arabinofuranosyluracil
7684
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS047722 [DBID]
AIDS-047722 [DBID]
AIDS097993 [DBID]
AIDS-097993 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 097557
    • Bio Activity:

      Anti-infection MedChem Express HY-13859
      Anti-infection; MedChem Express HY-13859
      Clevudine is an antiviral drug for the treatment of hepatitis B. MedChem Express http://www.medchemexpress.com/AZD1080.html, HY-13859
      Clevudine is an antiviral drug for the treatment of hepatitis B. ;Target: HBVClevudine is a nucleoside analog with an unnatural beta-L configuration. Clevudine showed potent antiviral activity during therapy and induced a sustained posttreatment antiviral effect for 6 months after a 12-week treatment period, and this was associated with a sustained normalization of ALT levels [1]. Clevudine showed a potent antiviral response, and its effect was higher in HBeAg-negative patients, with rapid viral load reduction after therapy. However, long-term therapy for more than 1 year resulted in the development of considerable resistance and myopathy. Therefore, we should consider alternative antiviral agents if clevudine resistance or clevudine-induced myopathy is developed in patients on clevudine for the treatment of CHB [2]. MedChem Express HY-13859
      HBV MedChem Express HY-13859

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

Density: 1.6±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.593
Molar Refractivity: 56.5±0.4 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: -0.72
ACD/LogD (pH 5.5): -1.27
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 4.84
ACD/LogD (pH 7.4): -1.27
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 4.81
Polar Surface Area: 99 Å2
Polarizability: 22.4±0.5 10-24cm3
Surface Tension: 65.9±5.0 dyne/cm
Molar Volume: 167.0±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) =  -0.78

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  527.78  (Adapted Stein & Brown method)
    Melting Pt (deg C):  225.58  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.53E-014  (Modified Grain method)
    Subcooled liquid VP: 7.82E-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):  4668
       log Kow used: -0.78 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  6.447e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.41E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.056E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.78  (KowWin est)
  Log Kaw used:  -15.006  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.226
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5938
   Biowin2 (Non-Linear Model)     :   0.1324
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9354  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7215  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3849
   Biowin6 (MITI Non-Linear Model):   0.0008
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.8751
 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):  1.04E-009 Pa (7.82E-012 mm Hg)
  Log Koa (Koawin est  ): 14.226
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.88E+003 
       Octanol/air (Koa) model:  41.3 
   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 =  32.9147 E-12 cm3/molecule-sec
      Half-Life =     0.325 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.900 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Hrs
   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: -0.78 (estimated)

 Volatilization from Water:
    Henry LC:  2.41E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.919E+013  hours   (1.633E+012 days)
    Half-Life from Model Lake : 4.275E+014  hours   (1.781E+013 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       9.59e-005       5.9          1000       
   Water     38.9            360          1000       
   Soil      61              720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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