ChemSpider 2D Image | Tenofovir alafenamide | C21H29N6O5P

Tenofovir alafenamide

  • Molecular FormulaC21H29N6O5P
  • Average mass476.466 Da
  • Monoisotopic mass476.193695 Da
  • ChemSpider ID7849225
  • defined stereocentres - 3 of 3 defined stereocentres


More details:






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

379270-37-8 [RN]
383365-04-6 [RN]
Isopropyl N-[(S)-({[(2R)-1-(6-amino-9H-purin-9-yl)-2-propanyl]oxy}methyl)(phenoxy)phosphoryl]-L-alaninate [ACD/IUPAC Name]
Isopropyl-N-[(S)-({[(2R)-1-(6-amino-9H-purin-9-yl)-2-propanyl]oxy}methyl)(phenoxy)phosphoryl]-L-alaninat [German] [ACD/IUPAC Name]
J4414G3BUK
L-Alanine, N-[(S)-[(1S)-[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]phenoxyphosphinyl]-, 1-methylethyl ester [ACD/Index Name]
N-[(S)-({[(2R)-1-(6-Amino-9H-purin-9-yl)-2-propanyl]oxy}méthyl)(phénoxy)phosphoryl]-L-alaninate d'isopropyle [French] [ACD/IUPAC Name]
tenofovir alafenamida [Spanish] [INN]
Tenofovir alafenamide [USAN]
ténofovir alafénamide [French] [INN]
More...

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

GS-7340 [DBID]
AIDS046774 [DBID]
AIDS-046774 [DBID]
GS-7339 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 098051
    • Chemical Class:

      An <stereo>L</stereo>-alanine derivative that is isopropyl <stereo>L</stereo>-alaninate in which one of the amino hydrogens is replaced by an (<stereo>S</stereo>)-({[(2<stereo>R</stereo>)-1-(6-amino-9 <element>H</element>-purin-9-yl)propan-2-yl]oxy}methyl)(phenoxy)phosphoryl group. A prodrug for tenofovir, it is used (as the fumarate salt) in combination therapy for the treatment of HIV-1 infection . ChEBI CHEBI:90926
    • Bio Activity:

      Anti-infection MedChem Express HY-15232
      Anti-infection; MedChem Express HY-15232
      GS-7340(Tenofovir alafenamide) is a prodrug of tenofovir (TFV) that more efficiently delivers TFV into lymphoid cells and tissues than TFV disoproxil fumarate. MedChem Express
      GS-7340(Tenofovir alafenamide) is a prodrug of tenofovir (TFV) that more efficiently delivers TFV into lymphoid cells and tissues than TFV disoproxil fumarate.; IC50 value:; Target: NRTI; HIV reverse transcriptase inhibitor; GS-7340 reduces first-pass clearance to be an effective oral prodrug, its permeability and stability were characterized in vitro and detailed pharmacokinetic studies were completed in dogs. MedChem Express HY-15232
      GS-7340(Tenofovir alafenamide) is a prodrug of tenofovir (TFV) that more efficiently delivers TFV into lymphoid cells and tissues than TFV disoproxil fumarate.;IC50 value:;Target: NRTI; HIV reverse transcriptase inhibitorGS-7340 reduces first-pass clearance to be an effective oral prodrug, its permeability and stability were characterized in vitro and detailed pharmacokinetic studies were completed in dogs. GS-7340 showed concentration-dependent permeability through monolayers of caco-2 cells and dose-dependent oral bioavailability in dogs, increasing from 1.7% at 2 mg/kg to 24.7% at 20 mg/kg, suggesting saturable intestinal efflux transport [1]. Significant reductions in plasma HIV-1 RNA from baseline to day 11 were observed for all TAF dose groups compared with placebo (P < 0.01), with a median decrease of 1.08-1.73 log10 copies per milliliter, including a dose-response relationship for viral load decrease up to 25 mg [2]. MedChem Express HY-15232
      HIV MedChem Express HY-15232
      HIV NRTIs MedChem Express HY-15232

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

Density: 1.4±0.1 g/cm3
Boiling Point: 640.4±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 94.5±3.0 kJ/mol
Flash Point: 341.1±34.3 °C
Index of Refraction: 1.630
Molar Refractivity: 121.8±0.5 cm3
#H bond acceptors: 11
#H bond donors: 3
#Freely Rotating Bonds: 12
#Rule of 5 Violations: 1
ACD/LogP: 2.20
ACD/LogD (pH 5.5): 2.21
ACD/BCF (pH 5.5): 27.46
ACD/KOC (pH 5.5): 364.28
ACD/LogD (pH 7.4): 2.24
ACD/BCF (pH 7.4): 29.74
ACD/KOC (pH 7.4): 394.55
Polar Surface Area: 153 Å2
Polarizability: 48.3±0.5 10-24cm3
Surface Tension: 55.1±7.0 dyne/cm
Molar Volume: 342.2±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) =  0.76

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  480.00  (Adapted Stein & Brown method)
    Melting Pt (deg C):  90.27  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.06E-008  (Modified Grain method)
    Subcooled liquid VP: 8.76E-008 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):  226.9
       log Kow used: 0.76 (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:
       Aromatic Amines
       Esters
       Esters (phosphate)
       Imidazoles

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.00E-022  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.692E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.76  (KowWin est)
  Log Kaw used:  -19.911  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  20.671
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2419
   Biowin2 (Non-Linear Model)     :   0.0386
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1648  (months      )
   Biowin4 (Primary Survey Model) :   3.2760  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.5119
   Biowin6 (MITI Non-Linear Model):   0.0002
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.7408
 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):  1.17E-005 Pa (8.76E-008 mm Hg)
  Log Koa (Koawin est  ): 20.671
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.257 
       Octanol/air (Koa) model:  1.15E+008 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.903 
       Mackay model           :  0.954 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 261.8823 E-12 cm3/molecule-sec
      Half-Life =     0.041 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    29.407 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.928 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  28.01
      Log Koc:  1.447 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  3.285E-002  L/mol-sec
  Kb Half-Life at pH 8:     244.164  days   
  Kb Half-Life at pH 7:       6.685  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 0.76 (estimated)

 Volatilization from Water:
    Henry LC:  3E-022 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  4.26E+018  hours   (1.775E+017 days)
    Half-Life from Model Lake : 4.647E+019  hours   (1.936E+018 days)

 Removal In Wastewater Treatment:
    Total removal:               1.87  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.78  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       3.59e-014       0.98         1000       
   Water     45.6            1.44e+003    1000       
   Soil      54.3            2.88e+003    1000       
   Sediment  0.0938          1.3e+004     0          
     Persistence Time: 1.24e+003 hr




                    

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