ChemSpider 2D Image | Trifluridine | C10H11F3N2O5

Trifluridine

  • Molecular FormulaC10H11F3N2O5
  • Average mass296.200 Da
  • Monoisotopic mass296.062012 Da
  • ChemSpider ID6020
  • defined stereocentres - 3 of 3 defined stereocentres


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Featured data source



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

1-(2-Deoxy-β-D-glycero-pentofuranosyl)-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-(trifluormethyl)pyrimidin-2,4(1H,3H)-dion
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxyméthyl)tétrahydrofuran-2-yl]-5-(trifluorométhyl)pyrimidine-2,4(1H,3H)-dione
2,4(1H,3H)-pyrimidinedione, 1-(2-deoxy-β-D-glycero-pentofuranosyl)-5-(trifluoromethyl)-
2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-β-D-ribofuranosyl)-5-(trifluoromethyl)-
200-722-8 [EINECS]
2'-Deoxy-5-(trifluoromethyl)uridine [ACD/IUPAC Name]
2'-Deoxy-5-trifluoromethyluridine
2'-Desoxy-5-(trifluormethyl)uridin [German] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS070980 [DBID]
AIDS-070980 [DBID]
BRN 0568095 [DBID]
CCRIS 2348 [DBID]
D00391 [DBID]
DRG-0120 [DBID]
MLS000028361 [DBID]
NSC 529182 [DBID]
NSC 75520 [DBID]
NSC529182 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      GHS07; GHS08 Biosynth W-104576
      H302; H312; H332; H351 Biosynth W-104576
      Harmful/Carcinogenic/Store at -20??C SynQuest 7809
      Harmful/Carcinogenic/Store at -20?C SynQuest 4H59-3-02
      Harmful/Carcinogenic/Store at -20°C SynQuest 4H59-3-02, 7809
      IRRITANT Matrix Scientific 072538
      P280 Biosynth W-104576
      R20/21/22,R40 SynQuest 4H59-3-02, 7809
      S01AD02 Wikidata Q2359590
      S22,S24/25,S26,S36/37/39,S45 SynQuest 4H59-3-02, 7809
      Warning Biosynth W-104576
    • Chemical Class:

      A pyrimidine 2'-deoxyribonucleoside compound having 5-trifluoromethyluracil as the nucleobase. An antiviral drug used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial k eratitis. ChEBI CHEBI:75179
    • Drug Status:

      approved BIONET-Key Organics HS-0007
    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-A0061
      Cell Cycle/DNA Damage; MedChem Express HY-A0061
      Nucleoside antimetabolite/analog MedChem Express HY-A0061
      Trifluorothymidine (TFT) and is an inhibitor of thymidine phosphorylase. MedChem Express http://www.medchemexpress.com/Verapamil-hydrochloride.html, HY-A0061
      Trifluorothymidine (TFT) and is an inhibitor of thymidine phosphorylase. TFT also inhibits thymidylate synthase (TS), a rate-limiting enzyme of DNA biosynthesis, and is incorporated into DNA.;IC50 Value: 1 uM ( Hela cell) [1];Target: thymidylate synthase; Nucleoside antimetabolite/analog;Trifluorothymidine (TFT) is well known to be converted to TFT-monophosphate by thymidine kinase and to inhibit thymidylate synthase;In vitro: When HeLa cells were treated with TFT at a concentration of 1 uM (IC50 value), the concentration of TFT in the DNA was calculated as 62.2?0.9 pmol/1x106 cells for 4 h [1]. Unlike FdUrd and 5FU, TFT resulted in an earlier phosphorylation of ATR and chk1 proteins after only 24 h of exposure, while phosphorylated ATM, BRCA2 and chk2 proteins were detected after more than 48 h of exposure to TFT [2]. SN38 and TFT induced most DNA damage in H630 and Colo320 cells, which was increased in combination. TFT pre-incubation further enhanced SN38-induced DNA strand brea MedChem Express HY-A0061

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

Density: 1.6±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.534
Molar Refractivity: 55.9±0.3 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 0.07
ACD/LogD (pH 5.5): -0.46
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 13.44
ACD/LogD (pH 7.4): -0.62
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 9.10
Polar Surface Area: 99 Å2
Polarizability: 22.2±0.5 10-24cm3
Surface Tension: 56.1±3.0 dyne/cm
Molar Volume: 179.9±3.0 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) =  -0.23
    Log Kow (Exper. database match) =  -0.46
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  521.82  (Adapted Stein & Brown method)
    Melting Pt (deg C):  222.79  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.52E-013  (Modified Grain method)
    MP  (exp database):  186-189 deg C
    Subcooled liquid VP: 1.21E-011 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):  1563
       log Kow used: -0.46 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.0397e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.53E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.284E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.46  (exp database)
  Log Kaw used:  -14.409  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.949
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.0562
   Biowin2 (Non-Linear Model)     :   0.0003
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3429  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3951  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3195
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.7952
 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):  1.61E-009 Pa (1.21E-011 mm Hg)
  Log Koa (Koawin est  ): 13.949
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.86E+003 
       Octanol/air (Koa) model:  21.8 
   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 =  75.3017 E-12 cm3/molecule-sec
      Half-Life =     0.142 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.705 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    :  10
      Log Koc:  1.000 

 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: -0.46 (expkow database)

 Volatilization from Water:
    Henry LC:  9.53E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.057E+013  hours   (4.406E+011 days)
    Half-Life from Model Lake : 1.153E+014  hours   (4.806E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       5.26e-005       3.34         1000       
   Water     46.2            900          1000       
   Soil      53.7            1.8e+003     1000       
   Sediment  0.089           8.1e+003     0          
     Persistence Time: 976 hr




                    

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