ChemSpider 2D Image | valganciclovir | C14H22N6O5

valganciclovir

  • Molecular FormulaC14H22N6O5
  • Average mass354.362 Da
  • Monoisotopic mass354.165161 Da
  • ChemSpider ID57721
  • defined stereocentres - 1 of 2 defined stereocentres


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175865-60-8 [RN]
2-((2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy)-3-hydroxypropyl L-Valinate
2-[(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]-3-hydroxypropyl L-valinate [ACD/IUPAC Name]
2-[(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]-3-hydroxypropyl-L-valinat [German] [ACD/IUPAC Name]
Cymeval [Trade name]
L-Valinate de 2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)méthoxy]-3-hydroxypropyle [French] [ACD/IUPAC Name]
L-Valine 2-[(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl Ester
L-Valine, 2-[(2-amino-3,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester [ACD/Index Name]
Valcyte [Trade name]
valganciclovir [INN] [Wiki]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:63635 [DBID]
AIDS032967 [DBID]
AIDS-032967 [DBID]
RS 79070 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      J05AB14 Wikidata Q423384
    • Chemical Class:

      The <stereo>L</stereo>-valinyl ester of ganciclovir, into which it is rapidly converted by intestinal and hepatic esterases. It is a synthetic analogue of 2'-deoxyguanosine. ChEBI CHEBI:63635
    • Bio Activity:

      Anti-infection MedChem Express HY-A0032
      Anti-infection; MedChem Express HY-A0032
      CMV MedChem Express HY-A0032
      Valganciclovir, the L-valyl ester of ganciclovir, is actually a prodrug for ganciclovir. MedChem Express http://www.medchemexpress.com/bazedoxifene-acetate.html, HY-A0032
      Valganciclovir, the L-valyl ester of ganciclovir, is actually a prodrug for ganciclovir. Valganciclovir is an antiviral medication used to treat cytomegalovirus infections.;IC50 Value: ;Target: CMV;In vitro: In cell culture model systems using Caco-2 cells for PEPT1 and SKPT cells for PEPT2, valganciclovir inhibited glycylsarcosine transport mediated by PEPT1 and PEPT2 with K(i) values (inhibition constant) of 1.68+/-0.30 and 0.043+/- 0.005 mM, respectively. The inhibition by valganciclovir was competitive in both cases [1].;In vivo: 37 patients were enrolled; 19 patients received treatment with VGV and 18 patients received treatment with GCV. The VGV was not inferior in efficacy to GCV as pre-emptive therapy, with rates of viral clearance at 28 days of 89.5% and 83%, respectively (P-value for non-inferiority = 0.030). Toxicities were similar between the 2 arms. No patients developed CMV disease [2]. Patients being treated with an alemtuzumab-containing regimen received prophylaxi MedChem Express HY-A0032

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

Density: 1.6±0.1 g/cm3
Boiling Point: 629.1±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 97.8±3.0 kJ/mol
Flash Point: 334.3±34.3 °C
Index of Refraction: 1.678
Molar Refractivity: 83.9±0.5 cm3
#H bond acceptors: 11
#H bond donors: 6
#Freely Rotating Bonds: 9
#Rule of 5 Violations: 2
ACD/LogP: -1.28
ACD/LogD (pH 5.5): -3.14
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.45
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 2.28
Polar Surface Area: 167 Å2
Polarizability: 33.3±0.5 10-24cm3
Surface Tension: 65.6±7.0 dyne/cm
Molar Volume: 222.5±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) =  -3.61

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  605.27  (Adapted Stein & Brown method)
    Melting Pt (deg C):  261.77  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.57E-016  (Modified Grain method)
    Subcooled liquid VP: 1E-013 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):  1e+006
       log Kow used: -3.61 (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:
       Aliphatic Amines
       Esters

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.14E-024  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.198E-022 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -3.61  (KowWin est)
  Log Kaw used:  -21.892  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.282
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7182
   Biowin2 (Non-Linear Model)     :   0.7015
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7320  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7284  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2070
   Biowin6 (MITI Non-Linear Model):   0.0230
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5215
 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):  1.33E-011 Pa (1E-013 mm Hg)
  Log Koa (Koawin est  ): 18.282
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.25E+005 
       Octanol/air (Koa) model:  4.7E+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 = 219.8564 E-12 cm3/molecule-sec
      Half-Life =     0.049 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.584 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.175000 E-17 cm3/molecule-sec
      Half-Life =     6.549 Days (at 7E11 mol/cm3)
   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    :  54.19
      Log Koc:  1.734 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  7.078E-005  L/mol-sec
  Kb Half-Life at pH 8:     310.307  years  
  Kb Half-Life at pH 7:    3103.073  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -3.61 (estimated)

 Volatilization from Water:
    Henry LC:  3.14E-024 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  3.51E+020  hours   (1.463E+019 days)
    Half-Life from Model Lake : 3.829E+021  hours   (1.595E+020 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       7.02e-010       1.16         1000       
   Water     46.5            900          1000       
   Soil      53.5            1.8e+003     1000       
   Sediment  0.0892          8.1e+003     0          
     Persistence Time: 973 hr




                    

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