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ChemSpider 2D Image | Linezolid | C16H20FN3O4

Linezolid

  • Molecular FormulaC16H20FN3O4
  • Average mass337.346 Da
  • Monoisotopic mass337.143799 Da
  • ChemSpider ID390139
  • defined stereocentres - 1 of 1 defined stereocentres


More details:



Featured data source



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

165800-03-3 [RN]
7584
AC2720000
Acetamide, N-(((5S)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)-
Acetamide, N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]- [ACD/Index Name]
linezolid [Spanish] [INN]
linézolide [French] [INN]
linezolidum [Latin] [INN]
MFCD00937825 [MDL number]
More...

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

CHEBI:63607 [DBID]
ISQ9I6J12J [DBID]
PNU-100766 [DBID]
U-100766 [DBID]
AIDS070944 [DBID]
AIDS-070944 [DBID]
AIDS110813 [DBID]
AIDS-110813 [DBID]
C08146 [DBID]
D00947 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Toxicity:

      Organic Compound; Amine; Organofluoride; Ether; Amide; Ester; Drug; Anti-Infective Agent; Anti-Bacterial Agent; Protein Synthesis Inhibitor; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D2675
    • Safety:

      5 Axon Medchem 2048
      GHS07 Biosynth Q-201308
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 2048
      H373 Biosynth Q-201308
      IRRITANT Matrix Scientific 095383
      J01XX08 Wikidata Q411377
      no pictogram Axon Medchem 2048
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 2048
      P261; P305+P351+P338 Biosynth Q-201308
      Sold for research purposes under agreement from Pfizer Inc. Tocris Bioscience 3765
      Warning Biosynth Q-201308
      Warning Axon Medchem 2048
    • Target Organs:

      Antibiotic; AO inhibitor TargetMol T0391
    • Chemical Class:

      An organofluorine compound that consists of 1,3-oxazolidin-2-one bearing an <element>N</element>-3-fluoro-4-(morpholin-4-yl)phenyl group as well as an acetamidomethyl group at position 5. A synthetic antibacterial agent that inhibits bacterial protein synthesis by binding to a site on 23S ribosomal RNA of the 50S subunit and prevents further formation of a functional 70S initiation complex. ChEBI CHEBI:63607
      An organofluorine compound that consists of 1,3-oxazolidin-2-one bearing an N-3-fluoro-4-(morpholin-4-yl)phenyl group as well as an acetamidomethyl group at position 5. A synthetic ; antibacterial age nt that inhibits bacterial protein synthesis by binding to a site on 23S ribosomal RNA of the 50S subunit and prevents further formation of a functional 70S initiation complex. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63607
    • Bio Activity:

      Antibacterial MedChem Express HY-10394
      Antibiotic; inhibits protein synthesis in gram-positive bacteria Tocris Bioscience 3765
      Anti-infection MedChem Express HY-10394
      Anti-infection; MedChem Express HY-10394
      AOA, AOB TargetMol T0391
      Cell Biology Tocris Bioscience 3765
      Cell Metabolism Tocris Bioscience 3765
      DNA, RNA and Protein Synthesis Tocris Bioscience 3765
      Linezolid(Zyvoxid) is a synthetic antibiotic used for the treatment of serious infections caused by Gram-positive bacteria that are resistant to several other antibiotics. MedChem Express HY-10394
      Linezolid(Zyvoxid) is a synthetic antibiotic used for the treatment of serious infections caused by Gram-positive bacteria that are resistant to several other antibiotics. ;IC50 value:;Target: AntibioticA member of the oxazolidinone class of drugs, linezolid is active against most Gram-positive bacteria that cause disease, including streptococci, vancomycin-resistant enterococci (VRE), and methicillin-resistant Staphylococcus aureus (MRSA). MedChem Express HY-10394
      Microbiology & Virology; Enzyme TargetMol T0391
      Oxazolidinone antibiotic. Inhibits bacterial protein synthesis prior to chain initiation. Displays potent antibacterial activity against a variety of multidrug-resistant gram-positive microbes in vitr o and in vivo. Tocris Bioscience 3765
      Oxazolidinone antibiotic. Inhibits bacterial protein synthesis prior to chain initiation. Displays potent antibacterial activity against a variety of multidrug-resistant gram-positive microbes in vitro and in vivo. Tocris Bioscience 3765

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

Density: 1.3±0.1 g/cm3
Boiling Point: 585.5±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 87.5±3.0 kJ/mol
Flash Point: 307.9±30.1 °C
Index of Refraction: 1.554
Molar Refractivity: 83.0±0.3 cm3
#H bond acceptors: 7
#H bond donors: 1
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 0.30
ACD/LogD (pH 5.5): 0.37
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 23.55
ACD/LogD (pH 7.4): 0.82
ACD/BCF (pH 7.4): 2.46
ACD/KOC (pH 7.4): 65.89
Polar Surface Area: 71 Å2
Polarizability: 32.9±0.5 10-24cm3
Surface Tension: 47.7±3.0 dyne/cm
Molar Volume: 259.0±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) =  1.26

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  519.49  (Adapted Stein & Brown method)
    Melting Pt (deg C):  221.70  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.92E-011  (Modified Grain method)
    Subcooled liquid VP: 8.79E-009 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):  613.5
       log Kow used: 1.27 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  12372 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.76E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.007E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.26  (KowWin est)
  Log Kaw used:  -12.143  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.403
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.4860
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.6823  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.4758  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0888
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.9644
 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):  1.17E-006 Pa (8.79E-009 mm Hg)
  Log Koa (Koawin est  ): 13.403
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.56 
       Octanol/air (Koa) model:  6.21 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.989 
       Mackay model           :  0.995 
       Octanol/air (Koa) model:  0.998 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 125.5393 E-12 cm3/molecule-sec
      Half-Life =     0.085 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.022 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.992 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  243.3
      Log Koc:  2.386 

 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 = 0.274 (BCF = 1.88)
       log Kow used: 1.27 (estimated)

 Volatilization from Water:
    Henry LC:  1.76E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  6.11E+010  hours   (2.546E+009 days)
    Half-Life from Model Lake : 6.665E+011  hours   (2.777E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               1.92  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.83  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       1.93e-005       2.04         1000       
   Water     42.8            4.32e+003    1000       
   Soil      57.1            8.64e+003    1000       
   Sediment  0.1             3.89e+004    0          
     Persistence Time: 1.84e+003 hr




                    

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