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ChemSpider 2D Image | Penciclovir | C10H15N5O3

Penciclovir

  • Molecular FormulaC10H15N5O3
  • Average mass253.258 Da
  • Monoisotopic mass253.117493 Da
  • ChemSpider ID4563

More details:



Featured data source



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

2-Amino-1,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)butyl]-6H-purin-6-one
2-Amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-1,9-dihydro-6H-purin-6-one [ACD/IUPAC Name]
2-Amino-9-[4-hydroxy-3-(hydroxyméthyl)butyl]-1,9-dihydro-6H-purin-6-one [French] [ACD/IUPAC Name]
39809-25-1 [RN]
6437
6H-Purin-6-one, 2-amino-3,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)butyl]- [ACD/Index Name]
9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]guanine
Denavir [Trade name]
Fenistil
MFCD15142866
More...

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

359HUE8FJC [DBID]
BRL-39123 [DBID]
AIDS070978 [DBID]
AIDS-070978 [DBID]
AIDS093112 [DBID]
AIDS-093112 [DBID]
AIDS093113 [DBID]
AIDS-093113 [DBID]
AIDS093114 [DBID]
AIDS-093114 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      36 LKT Labs [P1754]
      D06BB06 Wikidata Q420364
      H319 LKT Labs [P1754]
      J05AB13 Wikidata Q420364
      None LKT Labs [P1754]
      Xi LKT Labs [P1754]
    • Target Organs:

      DNA synthesis inhibitor;Thymidine kinase inducer TargetMol T1643
    • Chemical Class:

      A member of the class of 2-aminopurines that is guanine in which the hydrogen at position 9 is substituted by a 4-hydroxy-3-(hydroxymethyl)but-1-yl group. An antiviral drug, it is administered topical ly for treatment of herpes labialis. A prodrug, famciclovir, is used for oral administration. ChEBI CHEBI:7956
    • Bio Activity:

      Anti-infection MedChem Express HY-17424
      Anti-infection; MedChem Express HY-17424
      DNA Damage/DNA Repair TargetMol T1643
      DNA polymerase;Thymidine kinase TargetMol T1643
      HSV MedChem Express HY-17424
      Penciclovir, a novel acyclic nucleoside analogue, has demonstrated efficacy against HSV types 1 and 2 and seems to have a pharmacological advantage due to a prolonged half-life of its active form in H SV-infected cells. MedChem Express
      Penciclovir, a novel acyclic nucleoside analogue, has demonstrated efficacy against HSV types 1 and 2 and seems to have a pharmacological advantage due to a prolonged half-life of its active form in HSV-infected cells.; IC50 Value: 2.3?0.8 mg/ml(EC50, inhibition EBV DNA synthesis); >100mg/ml(50% cell growth inhibitory concentration of both P3HR-1 and Raji cells) [1]; Target: HSV; in vitro: Treatment with GCV or PCV induced rapid accumulation of cells in S-phase and apoptotic death, GCV (and to a lesser extent PCV) increased phosphatidyl serine translocation, induced positive TUNEL results with alterations in cell morphology, caused marked propidium iodide staining and induced DNA laddering. MedChem Express HY-17424
      Penciclovir, a novel acyclic nucleoside analogue, has demonstrated efficacy against HSV types 1 and 2 and seems to have a pharmacological advantage due to a prolonged half-life of its active form in HSV-infected cells.;IC50 Value: 2.3?0.8 mg/ml(EC50, inhibition EBV DNA synthesis); >100mg/ml(50% cell growth inhibitory concentration of both P3HR-1 and Raji cells) [1];Target: HSV;In vitro: Treatment with GCV or PCV induced rapid accumulation of cells in S-phase and apoptotic death, GCV (and to a lesser extent PCV) increased phosphatidyl serine translocation, induced positive TUNEL results with alterations in cell morphology, caused marked propidium iodide staining and induced DNA laddering. [2]. B-95-8 cells were treated with penciclovir or aciclovir at 1 and 10 ug/ml for 7 days, At 1 ug/ml, both compounds were inactive, but at 10 ug/ml, the virus yield relative to that of untreated virus controls was reduced by 94 and 86% by penciclovir and aciclovir, respectively[5].;In vivo: Penci MedChem Express HY-17424

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

Density: 1.7±0.1 g/cm3
Boiling Point: 653.4±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 101.1±3.0 kJ/mol
Flash Point: 348.9±34.3 °C
Index of Refraction: 1.749
Molar Refractivity: 61.1±0.5 cm3
#H bond acceptors: 8
#H bond donors: 5
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 1
ACD/LogP: -2.03
ACD/LogD (pH 5.5): -1.50
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 3.60
ACD/LogD (pH 7.4): -1.50
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 3.65
Polar Surface Area: 126 Å2
Polarizability: 24.2±0.5 10-24cm3
Surface Tension: 79.5±7.0 dyne/cm
Molar Volume: 150.2±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) =  -3.71

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  547.31  (Adapted Stein & Brown method)
    Melting Pt (deg C):  234.70  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.01E-014  (Modified Grain method)
    Subcooled liquid VP: 1.84E-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):  1e+006
       log Kow used: -3.71 (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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.57E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.366E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -3.71  (KowWin est)
  Log Kaw used:  -17.509  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.799
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9444
   Biowin2 (Non-Linear Model)     :   0.8386
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9594  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7412  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4404
   Biowin6 (MITI Non-Linear Model):   0.2161
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.0792
 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):  2.45E-010 Pa (1.84E-012 mm Hg)
  Log Koa (Koawin est  ): 13.799
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.22E+004 
       Octanol/air (Koa) model:  15.5 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 136.3967 E-12 cm3/molecule-sec
      Half-Life =     0.078 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.941 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    :  16.7
      Log Koc:  1.223 

 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: -3.71 (estimated)

 Volatilization from Water:
    Henry LC:  7.57E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.231E+016  hours   (5.128E+014 days)
    Half-Life from Model Lake : 1.343E+017  hours   (5.595E+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       1.34e-006       1.86         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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