ChemSpider 2D Image | Levofloxacin | C18H20FN3O4

Levofloxacin

  • Molecular FormulaC18H20FN3O4
  • Average mass361.367 Da
  • Monoisotopic mass361.143799 Da
  • ChemSpider ID131410

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

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

(3S)-9-Fluor-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]chinolin-6-carbonsäure [German] [ACD/IUPAC Name]
(3S)-9-Fluor-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]chinolin-6-carbonsäure [German]
(3S)-9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid [ACD/IUPAC Name]
(3S)-9-Fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid
100986-85-4 [RN]
7H-1,4-Oxazino[2,3,4-ij]quinoline-6-carboxylic acid, 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-, (3S)- [ACD/Index Name]
Acide (3S)-9-fluoro-3-méthyl-10-(4-méthyl-1-pipérazinyl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoléine-6-carboxylique [French] [ACD/IUPAC Name]
acide (3S)-9-fluoro-3-méthyl-10-(4-méthylpipérazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoléine-6-carboxylique [French]
Levaquin [Trade name]
levoflaxacin
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

6708 [DBID]
CHEBI:63598 [DBID]
DR 3355 [DBID]
DRG 0129 [DBID]
28266_FLUKA [DBID]
AIDS002307 [DBID]
AIDS-002307 [DBID]
AIDS002308 [DBID]
AIDS-002308 [DBID]
C07660 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Amine; Organofluoride; Ether; Amide; Ester; Drug; Food Toxin; Anti-Infective Agent, Urinary; Nucleic Acid Synthesis Inhibitor; Quinolone; Anti-Bacterial Agent; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D2478

    • Safety:

      J01MA12 Wikidata Q424193
      S01AE05 Wikidata Q424193

    • Chemical Class:

      An optically active form of ofloxacin having (<stereo>S</stereo>)-configuration; an inhibitor of bacterial topoisomerase IV and DNA gyrase ChEBI CHEBI:63598
      An optically active form of ofloxacin having (S)-configuration; an inhibitor of bacterial topoisomerase IV and DNA gyrase ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63598
      An optically active form of ofloxacin having (S)-configuration; an inhibitor of bacterial topoisomerase IV and DNA gyrase. ChEBI CHEBI:63598

    • Bio Activity:

      Antibacterial MedChem Express HY-B0330
      Anti-infection MedChem Express HY-B0330
      Anti-infection; MedChem Express HY-B0330
      Levofloxacin, a synthetic fluoroquinolone, is an antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication. MedChem Express
      Levofloxacin, a synthetic fluoroquinolone, is an antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication.; Target: Antibacterial; Levofloxacin reduced bacterial load compared with placebo by 4.9-fold (95% confidence interval, 1.4-25.7; P=0.02) at day 7 but had no effect at any point on any marker of neutrophilic airway inflammation. MedChem Express HY-B0330
      Levofloxacin, a synthetic fluoroquinolone, is an antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication.;Target: AntibacterialLevofloxacin reduced bacterial load compared with placebo by 4.9-fold (95% confidence interval, 1.4-25.7; P=0.02) at day 7 but had no effect at any point on any marker of neutrophilic airway inflammation. In patients with a baseline bacterial load of more than 10(6) cfu/mL, levofloxacin treatment was associated with a 26.5% (95% confidence interval, 1.8%-51.3%; P=0.04) greater reduction in the percentage neutrophil count compared with placebo at day 7 [1]. Levofloxacin was found to significantly improve the clinical and microbiological parameters in CP individuals [2]. A 30-day course of levofloxacin does not significantly improve BK viral load reduction or allograft function when used in addition to overall reduction of immunosuppression [3]. MedChem Express HY-B0330

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

Density: 1.5±0.1 g/cm3
Boiling Point: 571.5±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 90.1±3.0 kJ/mol
Flash Point: 299.4±30.1 °C
Index of Refraction: 1.670
Molar Refractivity: 91.1±0.4 cm3
#H bond acceptors: 7
#H bond donors: 1
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 0.84
ACD/LogD (pH 5.5): -1.84
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -2.08
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 73 Å2
Polarizability: 36.1±0.5 10-24cm3
Surface Tension: 70.3±5.0 dyne/cm
Molar Volume: 244.0±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) =  -2.00

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  573.54  (Adapted Stein & Brown method)
    Melting Pt (deg C):  317.69  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.82E-013  (Modified Grain method)
    Subcooled liquid VP: 3.6E-010 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):  6.762e+005
       log Kow used: -2.00 (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:
       Aliphatic Amines-acid
       Vinyl/Allyl Ketones-acid
       Vinyl/Allyl Ethers-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.16E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.280E-019 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.00  (KowWin est)
  Log Kaw used:  -19.324  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.324
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.3081
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9696  (months      )
   Biowin4 (Primary Survey Model) :   2.8160  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1754
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -3.7177
 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-008 Pa (3.6E-010 mm Hg)
  Log Koa (Koawin est  ): 17.324
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  62.5 
       Octanol/air (Koa) model:  5.18E+004 
   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 = 330.3014 E-12 cm3/molecule-sec
      Half-Life =     0.032 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    23.315 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.374000 E-17 cm3/molecule-sec
      Half-Life =     0.834 Days (at 7E11 mol/cm3)
      Half-Life =     20.017 Hrs
   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    :  44.44
      Log Koc:  1.648 

 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: -2.00 (estimated)

 Volatilization from Water:
    Henry LC:  1.16E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.595E+017  hours   (3.998E+016 days)
    Half-Life from Model Lake : 1.047E+019  hours   (4.361E+017 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       8.52e-011       0.748        1000       
   Water     49.5            1.44e+003    1000       
   Soil      50.4            2.88e+003    1000       
   Sediment  0.0962          1.3e+004     0          
     Persistence Time: 1.17e+003 hr

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