ChemSpider 2D Image | (+/-)-Gatifloxacin | C19H22FN3O4

(±)-Gatifloxacin

  • Molecular FormulaC19H22FN3O4
  • Average mass375.394 Da
  • Monoisotopic mass375.159424 Da
  • ChemSpider ID5186

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(±)-Gatifloxacin
112811-59-3 [RN]
1-Cyclopropyl-6-fluor-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-3-chinolincarbonsäure [German] [ACD/IUPAC Name]
1-Cyclopropyl-6-fluor-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydrochinolin-3-carbonsäure [German]
1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid [ACD/IUPAC Name]
1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo- [ACD/Index Name]
7423
81485Y3A9A
Acide 1-cyclopropyl-6-fluoro-8-méthoxy-7-(3-méthyl-1-pipérazinyl)-4-oxo-1,4-dihydro-3-quinoléinecarboxylique [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS044913 [DBID]
AIDS-044913 [DBID]
AIDS104746 [DBID]
AIDS-104746 [DBID]
AM 1155 [DBID]
AM-1155 [DBID]
BMS-206584 [DBID]
C07661 [DBID]
CG 5501 [DBID]
CG-5501 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      WHITE POWDER NIH Clinical Collection [SMR000043336]
    • Safety:

      0 SynQuest 4H29-3-39
      20/21/22 LKT Labs [G0278]
      H302 H312 H332 LKT Labs [G0278]
      J01MA16 Wikidata Q2365016
      None LKT Labs [G0278]
      S01AE06 Wikidata Q2365016
      Xn LKT Labs [G0278]
    • Target Organs:

      Topoisomerase inhibitor TargetMol T1293
    • Chemical Class:

      A monocarboxylic acid that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted on the nitrogen by a cyclopropyl group and at positions 6, 7, and 8 by fluoro, 3-methylpiperazin-1-yl, a nd methoxy groups, respectively. Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial topoisomerase type-II enz ymes. ChEBI CHEBI:5280
    • Drug Status:

      approved BIONET-Key Organics KS-1066
    • Compound Source:

      synthetic; BMS-206584-01, AM-1155 Microsource [01504272]
    • Bio Activity:

      Antibacterial MedChem Express HY-10581
      Antibacterial; Zerenex Molecular [ZBioX-0419]
      Antibiotic; inhibits bacterial type II topoisomerase Tocris Bioscience 3849
      Anti-infection MedChem Express HY-10581
      Anti-infection; MedChem Express HY-10581
      Cell Biology Tocris Bioscience 3849
      Cell Metabolism Tocris Bioscience 3849
      DNA Damage/DNA Repair TargetMol T1293
      DNA, RNA and Protein Synthesis Tocris Bioscience 3849
      Fluoroquinolone antibiotic. Inhibits bacterial type II topoisomerases (IC50 values are 0.109 and 13.8 ?g/ml for E.coli DNA gyrase and S.aureus topoisomerase IV respectively). Displays potent activity against gram-positive and gram-negative bacteria. Stimulates short-term self-renewal in both human and mouse embryonic stem cells in vitro. Tocris Bioscience 3849
      Fluoroquinolone antibiotic. Inhibits bacterial type II topoisomerases (IC50 values are 0.109 and 13.8 ?g/ml for E.coli DNA gyrase and S.aureus topoisomerase IV respectively). Displays potent activity against gram-positive and gram-negative bacteria. Stimulates short-term self-renewal in both human and mouse embryonic stem cells in vitro. Tocris Bioscience 3849
      Fluoroquinolone antibiotic. Inhibits bacterial type II topoisomerases (IC50 values are 0.109 and 13.8 mug/ml for E.coli DNA gyrase and S.aureus topoisomerase IV respectively). Displays potent activity against gram-positive and gram-negative bacteria. Stimulates short-term self-renewal in both human and mouse embryonic stem cells in vitro. Tocris Bioscience 3849
      Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, it inhibits the bacterial enzymes DNA gyrase and topoisomerase IV. MedChem Express
      Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, it inhibits the bacterial enzymes DNA gyrase and topoisomerase IV.; Target: Antibacterial; Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial enzymes DNA gyrase and topoisomerase IV. MedChem Express HY-10581
      Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, it inhibits the bacterial enzymes DNA gyrase and topoisomerase IV.;Target: AntibacterialGatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial enzymes DNA gyrase and topoisomerase IV. Gatifloxacin had activity equal to that of tosufloxacin and activity more potent than those of norfloxacin, ofloxacin, ciprofloxacin, and sparfloxacin against the second-step mutants (grlA gyrA; gatifloxacin MIC range, 1.56 to 3.13 microg/ml) and had the most potent activity against the third-step mutants (grlA gyrA grlA; gatifloxacin MIC range, 1.56 to 6.25 microg/ml), suggesting that gatifloxacin possesses the most potent inhibitory activity against singly mutated topo IV and singly mutated DNA gyrase among the quinolones tested [1].Ophthalmic gatifloxacin 0.3% is at least as effective as ciprofloxacin at healing corneal ulcers infect MedChem Express HY-10581
      Topoisomerase IV TargetMol T1293

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

Density: 1.4±0.1 g/cm3
Boiling Point: 607.8±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 95.0±3.0 kJ/mol
Flash Point: 321.4±31.5 °C
Index of Refraction: 1.616
Molar Refractivity: 94.6±0.3 cm3
#H bond acceptors: 7
#H bond donors: 2
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 1.21
ACD/LogD (pH 5.5): -2.62
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -2.13
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 82 Å2
Polarizability: 37.5±0.5 10-24cm3
Surface Tension: 57.8±3.0 dyne/cm
Molar Volume: 270.8±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) =  0.50

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  598.44  (Adapted Stein & Brown method)
    Melting Pt (deg C):  321.32  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.69E-014  (Modified Grain method)
    Subcooled liquid VP: 8.1E-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):  4051
       log Kow used: 0.50 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3137.3 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 :   4.00E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.499E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.50  (KowWin est)
  Log Kaw used:  -17.786  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.286
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.2864
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7615  (months      )
   Biowin4 (Primary Survey Model) :   3.2273  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1092
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.0127
 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):  1.08E-008 Pa (8.1E-011 mm Hg)
  Log Koa (Koawin est  ): 18.286
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  278 
       Octanol/air (Koa) model:  4.74E+005 
   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 = 135.4808 E-12 cm3/molecule-sec
      Half-Life =     0.079 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.947 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    :  42.66
      Log Koc:  1.630 

 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: 0.50 (estimated)

 Volatilization from Water:
    Henry LC:  4E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.836E+016  hours   (1.182E+015 days)
    Half-Life from Model Lake : 3.094E+017  hours   (1.289E+016 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       1.29e-008       1.87         1000       
   Water     47.3            1.44e+003    1000       
   Soil      52.6            2.88e+003    1000       
   Sediment  0.0948          1.3e+004     0          
     Persistence Time: 1.21e+003 hr




                    

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