ChemSpider 2D Image | Emtricitabine | C8H10FN3O3S

Emtricitabine

  • Molecular FormulaC8H10FN3O3S
  • Average mass247.247 Da
  • Monoisotopic mass247.042694 Da
  • ChemSpider ID54859
  • defined stereocentres - 2 of 2 defined stereocentres


More details:



Featured data source



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

(-)-FTC
(-)-β-L-FTC
143491-57-0 [RN]
2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]- [ACD/Index Name]
2'-deoxy-5-fluoro-3'-thiacytidine
4-Amino-5-fluor-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinon [German] [ACD/IUPAC Name]
4-Amino-5-fluor-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-on
4-Amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone [ACD/IUPAC Name]
4-Amino-5-fluoro-1-[(2R,5S)-2-(hydroxyméthyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone [French] [ACD/IUPAC Name]
4-Amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

DRG 0208 [DBID]
AIDS004782 [DBID]
AIDS-004782 [DBID]
BW 1592 [DBID]
C12599 [DBID]
D01199 [DBID]
DRG-0208 [DBID]
LS-135838 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 093781
      J05AF09 Wikidata Q422604
      TBC SynQuest 8H70-3-03
    • Chemical Class:

      An organofluorine compound that is 5-fluorocytosine substituted at the 1 position by a 2-(hydroxymethyl)-1,3-oxathiolan-5-yl group (2<stereo>R</stereo>,5<stereo>S</stereo> configuration). It is used in combination therapy for the treatment of HIV-1 infection. ChEBI CHEBI:31536
    • Bio Activity:

      Anti-infection MedChem Express HY-17427
      Anti-infection; MedChem Express HY-17427
      Emtricitabine(BW1592) is a nucleoside reverse transcriptase inhibitor (NRTI) for the treatment of HIV infection. MedChem Express
      Emtricitabine(BW1592) is a nucleoside reverse transcriptase inhibitor (NRTI) for the treatment of HIV infection.; IC50 Value: 1.01uM (EC50 values obtained for FTC against the NL4-3 reference laboratory strain of HIV) [1]; Target: NRTI; in vitro: Mean EC50 values obtained for FTC and 3TC against the NL4-3 reference laboratory strain of HIV were 1.01 and 2.79 uM, respectively. MedChem Express HY-17427
      Emtricitabine(BW1592) is a nucleoside reverse transcriptase inhibitor (NRTI) for the treatment of HIV infection.;IC50 Value: 1.01uM (EC50 values obtained for FTC against the NL4-3 reference laboratory strain of HIV) [1];Target: NRTI;In vitro: Mean EC50 values obtained for FTC and 3TC against the NL4-3 reference laboratory strain of HIV were 1.01 and 2.79 uM, respectively. When tested against a panel of 100 WT clinical isolates, FTC and 3TC had identical mean FC values when compared with NL4-3 of 0.9 [1]. In CEM cells, there was a statistically significant increase in the levels of TFV diphosphate (P=0.047) and FTC triphosphate (P=0.0069) following a 24 h incubation with the combination compared with the levels seen with the individual drugs [2].;In vivo: Oral doses up to 1000 mg/kg/day provided daily area under the curve (AUC(0-->24)) exposure to pregnant animals approximately 60- (mice) to 120-fold (rabbits) higher than that in humans at the recommended dose of 200 mg given once MedChem Express HY-17427
      HIV MedChem Express HY-17427
      HIV NRTIs MedChem Express HY-17427

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

Density: 1.8±0.1 g/cm3
Boiling Point: 443.3±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.4 mmHg at 25°C
Enthalpy of Vaporization: 80.9±6.0 kJ/mol
Flash Point: 221.9±31.5 °C
Index of Refraction: 1.731
Molar Refractivity: 54.0±0.5 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: -0.41
ACD/LogD (pH 5.5): -0.73
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 9.53
ACD/LogD (pH 7.4): -0.73
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 9.54
Polar Surface Area: 113 Å2
Polarizability: 21.4±0.5 10-24cm3
Surface Tension: 72.8±7.0 dyne/cm
Molar Volume: 135.2±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) =  -2.56

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  397.29  (Adapted Stein & Brown method)
    Melting Pt (deg C):  164.62  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.13E-009  (Modified Grain method)
    Subcooled liquid VP: 2.22E-007 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):  1.857e+005
       log Kow used: -2.56 (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:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.08E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.424E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.56  (KowWin est)
  Log Kaw used:  -15.355  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.795
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4412
   Biowin2 (Non-Linear Model)     :   0.0566
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8041  (weeks       )
   Biowin4 (Primary Survey Model) :   3.6107  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2568
   Biowin6 (MITI Non-Linear Model):   0.0007
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6230
 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):  2.96E-005 Pa (2.22E-007 mm Hg)
  Log Koa (Koawin est  ): 12.795
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.101 
       Octanol/air (Koa) model:  1.53 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.785 
       Mackay model           :  0.89 
       Octanol/air (Koa) model:  0.992 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 134.4023 E-12 cm3/molecule-sec
      Half-Life =     0.080 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.955 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.070000 E-17 cm3/molecule-sec
      Half-Life =    16.371 Days (at 7E11 mol/cm3)
   Fraction sorbed to airborne particulates (phi): 0.838 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  32.77
      Log Koc:  1.515 

 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: -2.56 (estimated)

 Volatilization from Water:
    Henry LC:  1.08E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.524E+013  hours   (3.552E+012 days)
    Half-Life from Model Lake : 9.299E+014  hours   (3.875E+013 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       1.43e-009       1.9          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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