ChemSpider 2D Image | trovafloxacin | C20H15F3N4O3

trovafloxacin

  • Molecular FormulaC20H15F3N4O3
  • Average mass416.353 Da
  • Monoisotopic mass416.109619 Da
  • ChemSpider ID16736478

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(1a,5a,6a)-7-(6-Amino-3-azabicyclo[3.1.0]hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
1,8-Naphthyridine-3-carboxylic acid, 7-[(1R,5S)-6-amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo- [ACD/Index Name]
147059-72-1 [RN]
7-[(1R,5S,6s)-6-Amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid [ACD/IUPAC Name]
7-[(1R,5S,6s)-6-Amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorphenyl)-6-fluor-4-oxo-1,4-dihydro-1,8-naphthyridin-3-carbonsäure [German] [ACD/IUPAC Name]
9F388J00UK
Acide 7-[(1R,5S,6s)-6-amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophényl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphtyridine-3-carboxylique [French] [ACD/IUPAC Name]
trovafloxacin [INN] [Wiki]
Trovan [Trade name]
Turvel
More...

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

7370 [DBID]
CP 99219 [DBID]
  • Miscellaneous

    • Safety:

      J01MA13 Wikidata Q544393

    • Chemical Class:

      A 1,8-naphthyridine derivative that is 4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid bearing additional 2,4-difluorophenyl, fluoro and 6-amino-3-azabicyclo[3.1.0]hex-3-yl substituents at posi tions 1, 6 and 7 respectively. A broad-spectrum antibiotic that was withdrawn from the market due to risk of liver failure. ChEBI CHEBI:9763

    • Therapeutical Effect:

      Antimalarials,Antiprotozoal Agents,Folic Acid Antagonists Sean Ekins

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

Density: 1.6±0.1 g/cm3
Boiling Point: 630.5±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 98.0±3.0 kJ/mol
Flash Point: 335.1±31.5 °C
Index of Refraction: 1.673
Molar Refractivity: 96.8±0.3 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 0.96
ACD/LogD (pH 5.5): -1.58
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.56
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 100 Å2
Polarizability: 38.4±0.5 10-24cm3
Surface Tension: 71.6±3.0 dyne/cm
Molar Volume: 258.3±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) =  1.55
    Log Kow (Exper. database match) =  0.31
       Exper. Ref:  Daylight (2002)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  618.12  (Adapted Stein & Brown method)
    Melting Pt (deg C):  324.19  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.04E-014  (Modified Grain method)
    Subcooled liquid VP: 2.48E-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):  3271
       log Kow used: 0.31 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  42028 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines-acid
       Vinyl/Allyl Ketones-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.04E-022  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.742E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.31  (exp database)
  Log Kaw used:  -20.371  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  20.681
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -2.2124
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   0.7010  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.0993  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2295
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.2773
 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):  3.31E-009 Pa (2.48E-011 mm Hg)
  Log Koa (Koawin est  ): 20.681
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  907 
       Octanol/air (Koa) model:  1.18E+008 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  43.9889 E-12 cm3/molecule-sec
      Half-Life =     0.243 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.918 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    :  1712
      Log Koc:  3.234 

 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: 0.31 (expkow database)

 Volatilization from Water:
    Henry LC:  1.04E-022 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.149E+019  hours   (4.786E+017 days)
    Half-Life from Model Lake : 1.253E+020  hours   (5.221E+018 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       8.72e-011       5.63         1000       
   Water     52.4            4.32e+003    1000       
   Soil      47.5            8.64e+003    1000       
   Sediment  0.105           3.89e+004    0          
     Persistence Time: 1.55e+003 hr

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