ChemSpider 2D Image | Valaciclovir | C13H20N6O4

Valaciclovir

  • Molecular FormulaC13H20N6O4
  • Average mass324.336 Da
  • Monoisotopic mass324.154602 Da
  • ChemSpider ID54770

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

Valaciclovir [INN] [Wiki]
124832-26-4 [RN]
2-[(2-amino-6-hydroxy-9H-purin-9-yl)methoxy]ethyl L-valinate
2-[(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl L-valinate [ACD/IUPAC Name]
2-[(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl-L-valinat [German] [ACD/IUPAC Name]
2-{[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]oxy}ethyl L-valinate
L-Valinate de 2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)méthoxy]éthyle [French] [ACD/IUPAC Name]
L-Valine 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester
L-valine ester with 9-[(2-hydroxyethoxy)methyl]guanine
L-Valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

7106 [DBID]
AIDS070982 [DBID]
AIDS-070982 [DBID]
CHEBI:35854 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Amine; Ether; Amide; Ester; Drug; Antiviral Agent; Metabolite; Prodrug; Synthetic Compound Toxin, Toxin-Target Database T3D3542

    • Safety:

      J05AB11 Wikidata Q418594

    • Bio Activity:

      Anti-infection MedChem Express HY-17425
      Anti-infection; MedChem Express HY-17425
      HSV MedChem Express HY-17425
      Valacyclovir is an antiviral drug used in the management of herpes simplex, herpes zoster, and herpes B. MedChem Express http://www.medchemexpress.com/Zidovudine.html, HY-17425
      Valacyclovir is an antiviral drug used in the management of herpes simplex, herpes zoster, and herpes B. ;IC50 Value: 2.9 microg/ml (for HSV-1 W)[4]. ;Target: HSV infection;In vitro: VACV uptake was concentration dependent and saturable with a Michaelis-Menten constant and maximum velocity of 1.64 +/- 0.06 mM and 23.34 +/- 0.36 nmol/mg protein/5 min, respectively. A very similar Km value was obtained in hPEPT1/CHO cells and in rat and rabbit tissues and Caco-2 cells, suggesting that hPEPT1 dominates the intestinal transport properties of VACV in vitro [5]. ;In vivo: For treatment of a first episode of genital herpes, a large comparative trial has shown that valacyclovir (1 g twice a day) is as effective as acyclovir (200 mg five times a day) when given for 10 days. For treating recurrences, two trials show that valacyclovir is as effective as acyclovir (200 mg five times a day) with a treatment period of 5 days. A daily dose of 1 g of valacyclovir is as effective as 2 g daily. Val MedChem Express HY-17425

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.5±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.673
Molar Refractivity: 78.4±0.5 cm3
#H bond acceptors: 10
#H bond donors: 5
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 2
ACD/LogP: -0.88
ACD/LogD (pH 5.5): -3.17
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.49
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 2.14
Polar Surface Area: 147 Å2
Polarizability: 31.1±0.5 10-24cm3
Surface Tension: 62.9±7.0 dyne/cm
Molar Volume: 209.2±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) =  -3.41

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  557.21  (Adapted Stein & Brown method)
    Melting Pt (deg C):  239.32  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.59E-012  (Modified Grain method)
    Subcooled liquid VP: 9.5E-010 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: -3.41 (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 :   6.46E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.959E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -3.41  (KowWin est)
  Log Kaw used:  -17.578  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.168
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5738
   Biowin2 (Non-Linear Model)     :   0.5407
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6384  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6423  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1859
   Biowin6 (MITI Non-Linear Model):   0.0222
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5546
 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):  1.27E-007 Pa (9.5E-010 mm Hg)
  Log Koa (Koawin est  ): 14.168
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  23.7 
       Octanol/air (Koa) model:  36.1 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 204.7997 E-12 cm3/molecule-sec
      Half-Life =     0.052 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.627 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): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  572.5
      Log Koc:  2.758 

 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: -3.41 (estimated)

 Volatilization from Water:
    Henry LC:  6.46E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.632E+016  hours   (6.801E+014 days)
    Half-Life from Model Lake : 1.781E+017  hours   (7.419E+015 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       1.35e-009       1.24         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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