ChemSpider 2D Image | Lersivirine | C17H18N4O2

Lersivirine

  • Molecular FormulaC17H18N4O2
  • Average mass310.350 Da
  • Monoisotopic mass310.142975 Da
  • ChemSpider ID10705150

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

1,3-Benzenedicarbonitrile, 5-((3,5-diethyl-1-(2- hydroxyethyl)-1H-pyrazol-4-yl)oxy)-
1,3-Benzenedicarbonitrile, 5-[[3,5-diethyl-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]oxy]- [ACD/Index Name]
473921-12-9 [RN]
5-((3,5-Diethyl-1-(2-hydroxyethyl)-1H-pyrazol-4- yl)oxy)benzene-1,3-dicarbonitrile
5-{[3,5-diethyl-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]oxy}benzene-1,3-dicarbonitrile
5-{[3,5-Diéthyl-1-(2-hydroxyéthyl)-1H-pyrazol-4-yl]oxy}isophtalonitrile [French] [ACD/IUPAC Name]
5-{[3,5-Diethyl-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]oxy}isophthalonitril [German] [ACD/IUPAC Name]
5-{[3,5-Diethyl-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]oxy}isophthalonitrile [ACD/IUPAC Name]
lersivirina [Spanish] [INN]
Lersivirine [INN] [USAN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

UK-453,061 [DBID]
UK-453061 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Bio Activity:

      Anti-infection; MedChem Express HY-14267
      HIV NNRTIs MedChem Express HY-14267
      Lersivirine(UK-453061) is a next-generation non-nucleoside reverse transcriptase inhibitor (NNRTI, IC50=119 nM) with a unique resistance profile that exhibits potent antiretroviral activity against wi ld-type human immunodeficiency virus and clinically relevant NNRTI-resistant strains. MedChem Express
      Lersivirine(UK-453061) is a next-generation non-nucleoside reverse transcriptase inhibitor (NNRTI, IC50=119 nM) with a unique resistance profile that exhibits potent antiretroviral activity against wild-type human immunodeficiency virus and clinically relevant NNRTI-resistant strains.;IC50 value: 0.119 uM [1];Target: NNRTIUK-453061(Compound 5) demonstrated excellent activity against large panels of wild type and drug-resistant HIV consistent with the encouraging profile demonstrated against the isolated RT enzymes. Compound 5 can be readily prepared in multi-gram quantities by virtue of the efficient and concise synthetic route. The compound also has good aqueous solubility and formulation characteristics which enable further in vivo evaluation. Clinical trials evaluating the potential of 5 (UK-453,061, lersivirine) to treat HIV infection are proceeding and further progress will be reported in due course [1].At clinically relevant lersivirine doses (500-1,000 mg total daily dose MedChem Express HY-14267

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

Density: 1.2±0.1 g/cm3
Boiling Point: 455.4±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 75.4±3.0 kJ/mol
Flash Point: 229.2±28.7 °C
Index of Refraction: 1.595
Molar Refractivity: 88.5±0.5 cm3
#H bond acceptors: 6
#H bond donors: 1
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 3.30
ACD/LogD (pH 5.5): 2.66
ACD/BCF (pH 5.5): 61.88
ACD/KOC (pH 5.5): 666.75
ACD/LogD (pH 7.4): 2.66
ACD/BCF (pH 7.4): 61.89
ACD/KOC (pH 7.4): 666.90
Polar Surface Area: 95 Å2
Polarizability: 35.1±0.5 10-24cm3
Surface Tension: 46.3±7.0 dyne/cm
Molar Volume: 260.3±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) =  2.02

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  485.48  (Adapted Stein & Brown method)
    Melting Pt (deg C):  205.82  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.29E-012  (Modified Grain method)
    Subcooled liquid VP: 5.17E-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):  109.3
       log Kow used: 2.02 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  25.46 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.68E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.350E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.02  (KowWin est)
  Log Kaw used:  -12.163  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.183
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.6138
   Biowin2 (Non-Linear Model)     :   1.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3007  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3391  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3014
   Biowin6 (MITI Non-Linear Model):   0.0672
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5098
 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):  6.89E-008 Pa (5.17E-010 mm Hg)
  Log Koa (Koawin est  ): 14.183
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  43.5 
       Octanol/air (Koa) model:  37.4 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  43.5966 E-12 cm3/molecule-sec
      Half-Life =     0.245 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.944 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    :  509.7
      Log Koc:  2.707 

 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 = 0.205 (BCF = 1.604)
       log Kow used: 2.02 (estimated)

 Volatilization from Water:
    Henry LC:  1.68E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  6.14E+010  hours   (2.558E+009 days)
    Half-Life from Model Lake : 6.698E+011  hours   (2.791E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               2.26  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.17  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       0.000373        5.89         1000       
   Water     22.7            900          1000       
   Soil      77.2            1.8e+003     1000       
   Sediment  0.0896          8.1e+003     0          
     Persistence Time: 1.43e+003 hr

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