ChemSpider 2D Image | nalidixic acid | C12H12N2O3

nalidixic acid

  • Molecular FormulaC12H12N2O3
  • Average mass232.235 Da
  • Monoisotopic mass232.084793 Da
  • ChemSpider ID4268

More details:

Featured data source
The Merck Index Online

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

1,4-Dihydro-1-ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic acid
1,8-Naphthyridine-3-carboxylic acid, 1-ethyl-1,4-dihydro-7-methyl-4-oxo- [ACD/Index Name]
1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure [German]
1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridin-3-carbonsäure [German] [ACD/IUPAC Name]
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid [ACD/IUPAC Name]
222-159-7 [EINECS]
389-08-2 [RN]
Acide 1-éthyl-7-méthyl-4-oxo-1,4-dihydro-1,8-naphtyridine-3-carboxylique [French] [ACD/IUPAC Name]
Acide 1-etil-7-metil-1,8-naftiridin-4-one-3-carbossilico [Italian]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

1450 [DBID]
3B91HWA56M [DBID]
MFCD00006884 [DBID]
75015 [DBID]
AIDS001989 [DBID]
AIDS-001989 [DBID]
AIDS032293 [DBID]
AIDS-032293 [DBID]
BRN 0750515 [DBID]
C05079 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous

    • Appearance:

      cream-coloured powder OU Chemical Safety Data (No longer updated) More details

    • Stability:

      Stable. Incompatible with strong oxidizing agents. OU Chemical Safety Data (No longer updated) More details

    • Toxicity:

      ORL-RAT LD50 2040 mg kg-1, ORL-MUS LD50 572 mg kg-1, IVN-MUS LD50 180 mg kg-1, IPR-RAT LD50 319 mg kg-1 OU Chemical Safety Data (No longer updated) More details

    • Safety:

      22 Alfa Aesar B25096
      36 Alfa Aesar B25096
      H302 Alfa Aesar B25096
      J01MB02 Wikidata Q281082
      P264-P270-P301+P312-P330-P501a Alfa Aesar B25096
      Safety glasses, adequate ventilation. OU Chemical Safety Data (No longer updated) More details
      Warning Alfa Aesar B25096

    • Target Organs:

      Topoisomerase inhibitor TargetMol T0909

    • Chemical Class:

      A monocarboxylic acid comprising 1,8-naphthyridin-4-one substituted by carboxylic acid, ethyl and methyl groups at positions 3, 1, and 7, respectively. An orally administered antibacterial, it is used in the treatment of lower urinary-tract infections due to Gram-negative bacteria, including the majority of <ital>E. coli</ital>, <ital>Enterobacter</ital>, <ital>Klebsiella</ital>, and <ital>Proteus </ital> species. ChEBI CHEBI:100147

    • Bio Activity:

      Antibacterial MedChem Express HY-B0398
      Anti-infection MedChem Express HY-B0398
      Anti-infection; MedChem Express HY-B0398
      DNA Damage/DNA Repair TargetMol T0909
      Nalidixic acid is a synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. MedChem Express
      Nalidixic acid is a synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum.; Target: Antibacterial; Nalidixic acid is the first of the synthetic quinolone antibiotics. MedChem Express HY-B0398
      Nalidixic acid is a synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum.;Target: AntibacterialNalidixic acid is the first of the synthetic quinolone antibiotics. Nalidixic acid is effective against both gram-positive and gram-negative bacteria. In lower concentrations, it acts in a bacteriostatic manner; that is, it inhibits growth and reproduction. In higher concentrations, it is bactericidal, meaning that it kills bacteria instead of merely inhibiting their growth. Nalidixic selectively and reversibly blocks DNA replication in susceptible bacteria. Nalidixic acid and related antibiotics inhibit a subunit of DNA gyrase and topoisomerase IV and induce formation of cleavage complexes. It also inhibits the nicking-closing activity on the subunit of DNA gyrase that releases the positive binding stress on the supercoiled DNA. From Wikipedia. MedChem Express HY-B0398
      Topoisomerase II TargetMol T0909
  • Gas Chromatography

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

Density: 1.3±0.1 g/cm3
Boiling Point: 413.1±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 70.2±3.0 kJ/mol
Flash Point: 203.6±28.7 °C
Index of Refraction: 1.605
Molar Refractivity: 60.1±0.3 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 1.19
ACD/LogD (pH 5.5): 0.63
ACD/BCF (pH 5.5): 1.27
ACD/KOC (pH 5.5): 27.90
ACD/LogD (pH 7.4): -0.32
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 3.08
Polar Surface Area: 71 Å2
Polarizability: 23.8±0.5 10-24cm3
Surface Tension: 59.3±3.0 dyne/cm
Molar Volume: 174.4±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) =  1.64
    Log Kow (Exper. database match) =  1.59
       Exper. Ref:  BioByte (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  397.21  (Adapted Stein & Brown method)
    Melting Pt (deg C):  164.58  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.17E-008  (Modified Grain method)
    MP  (exp database):  229.5 deg C
    Subcooled liquid VP: 9.72E-006 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):  3224
       log Kow used: 1.59 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  100 mg/L (23 deg C)
        Exper. Ref:  MERCK INDEX (1996)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.5005e+005 mg/L
    Wat Sol (Exper. database match) =  100.00
       Exper. Ref:  MERCK INDEX (1996)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.12E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.848E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.59  (exp database)
  Log Kaw used:  -13.679  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.269
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4113
   Biowin2 (Non-Linear Model)     :   0.0328
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4843  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5008  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3157
   Biowin6 (MITI Non-Linear Model):   0.0769
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4926
 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):  0.0013 Pa (9.72E-006 mm Hg)
  Log Koa (Koawin est  ): 15.269
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00231 
       Octanol/air (Koa) model:  456 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0772 
       Mackay model           :  0.156 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  21.5038 E-12 cm3/molecule-sec
      Half-Life =     0.497 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     5.969 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): 0.117 (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: 1.59 (expkow database)

 Volatilization from Water:
    Henry LC:  5.12E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.743E+012  hours   (7.261E+010 days)
    Half-Life from Model Lake : 1.901E+013  hours   (7.921E+011 days)

 Removal In Wastewater Treatment:
    Total removal:               2.00  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.91  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       9.16e-009       11.1         1000       
   Water     31.1            900          1000       
   Soil      68.8            1.8e+003     1000       
   Sediment  0.083           8.1e+003     0          
     Persistence Time: 1.23e+003 hr

Click to predict properties on the Chemicalize site


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