ChemSpider 2D Image | Finafloxacin | C20H19FN4O4

Finafloxacin

  • Molecular FormulaC20H19FN4O4
  • Average mass398.388 Da
  • Monoisotopic mass398.139038 Da
  • ChemSpider ID9742243
  • defined stereocentres - 2 of 2 defined stereocentres


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209342-40-5 [RN]
3-Quinolinecarboxylic acid, 8-cyano-1-cyclopropyl-6-fluoro-7-[(4aS,7aS)-hexahydropyrrolo[3,4-b]-1,4-oxazin-6(2H)-yl]-1,4-dihydro-4-oxo- [ACD/Index Name]
8-Cyan-1-cyclopropyl-6-fluor-7-[(4aS,7aS)-hexahydropyrrolo[3,4-b][1,4]oxazin-6(2H)-yl]-4-oxo-1,4-dihydro-3-chinolincarbonsäure [German] [ACD/IUPAC Name]
8-Cyano-1-cyclopropyl-6-fluoro-7-[(4aS,7aS)-hexahydropyrrolo[3,4-b][1,4]oxazin-6(2H)-yl]-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid [ACD/IUPAC Name]
Acide 8-cyano-1-cyclopropyl-6-fluoro-7-[(4aS,7aS)-hexahydropyrrolo[3,4-b][1,4]oxazin-6(2H)-yl]-4-oxo-1,4-dihydro-3-quinoléinecarboxylique [French] [ACD/IUPAC Name]
Finafloxacin [INN] [USAN]
finafloxacine [French] [INN]
finafloxacino [Spanish] [INN]
finafloxacinum [Latin] [INN]
Xtoro [Trade name]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A quinolone that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted at positions 1, 6, 7 and 8 by cyclopropyl, fluoro, hexahydropyrrolo[3,4-<ital>b</ital>][1,4]oxazin-6-yl and cyano groups respectively; an antibiotic used for treatment of acute otitis externa (swimmer's ear) caused by the bacteria <ital>Pseudomonas aeruginosa</ital> and <ital>Staphylococcus aureus</ital>. ChEBI CHEBI:85176
      A quinolone that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted at positions 1, 6, 7 and 8 by cyclopropyl, fluoro, hexahydropyrrolo[3,4-b][1,4]oxazin-6-yl and cyano ; groups resp ectively; an antibiotic used for treatment of acute otitis externa (swimmer's ear) caused by the bacteria Pseudomonas aeruginosa and Staphylococcus aureus. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:85176
    • Bio Activity:

      Antibacterial MedChem Express HY-13451
      Anti-infection; MedChem Express HY-13451
      Finafloxacin is a fluoroquinolone antimicrobial agent that exhibits optimum efficacy in slightly acidic environments. ;Target: AntibacterialFinafloxacin is a pH-activated fluoroquinolone (belonging to a new 8-cyano subclass) to treat serious bacterial infections associated with an acidic environment, including urinary tract infections (UTIs) and Helicobacter pylori infections. Finafloxacin exhibits optimal efficacy in slightly acidic environments (pH 5.0-6.0), under which other fluoroquinolones lose activity. Finafloxacin is highly selective for bacterial type II topoisomerases, including DNA gyrase and DNA topoisomerase IV. [1] MedChem Express HY-13451

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

Density: 1.6±0.1 g/cm3
Boiling Point: 686.2±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 105.7±3.0 kJ/mol
Flash Point: 368.8±31.5 °C
Index of Refraction: 1.700
Molar Refractivity: 98.0±0.4 cm3
#H bond acceptors: 8
#H bond donors: 2
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: -0.85
ACD/LogD (pH 5.5): -2.70
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.92
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 106 Å2
Polarizability: 38.8±0.5 10-24cm3
Surface Tension: 82.7±5.0 dyne/cm
Molar Volume: 253.4±5.0 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) =  -1.33

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  649.90  (Adapted Stein & Brown method)
    Melting Pt (deg C):  328.83  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.31E-015  (Modified Grain method)
    Subcooled liquid VP: 3.6E-012 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):  5.775e+004
       log Kow used: -1.33 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  11395 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 :   3.37E-023  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.189E-020 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.33  (KowWin est)
  Log Kaw used:  -20.861  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.531
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.4696
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.6777  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.0421  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0500
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.3694
 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):  4.8E-010 Pa (3.6E-012 mm Hg)
  Log Koa (Koawin est  ): 19.531
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6.25E+003 
       Octanol/air (Koa) model:  8.34E+006 
   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 = 150.6378 E-12 cm3/molecule-sec
      Half-Life =     0.071 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.852 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: -1.33 (estimated)

 Volatilization from Water:
    Henry LC:  3.37E-023 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.468E+019  hours   (1.445E+018 days)
    Half-Life from Model Lake : 3.783E+020  hours   (1.576E+019 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       2.07e-010       1.69         1000       
   Water     53.9            4.32e+003    1000       
   Soil      46              8.64e+003    1000       
   Sediment  0.106           3.89e+004    0          
     Persistence Time: 1.51e+003 hr




                    

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