ChemSpider 2D Image | pretomanid | C14H12F3N3O5

pretomanid

  • Molecular FormulaC14H12F3N3O5
  • Average mass359.257 Da
  • Monoisotopic mass359.072906 Da
  • ChemSpider ID401693
  • defined stereocentres - 1 of 1 defined stereocentres


More details:






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

pretomanid [INN] [USAN]
(6S)-2-Nitro-6-{[4-(trifluormethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin [German] [ACD/IUPAC Name]
(6S)-2-Nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine [ACD/IUPAC Name]
(6S)-2-Nitro-6-{[4-(trifluorométhoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine [French] [ACD/IUPAC Name]
187235-37-6 [RN]
2XOI31YC4N
5H-Imidazo(2,1-b)(1,3)oxazine, 6,7-dihydro-2-nitro-6-((4-(trifluoromethoxy)phenyl)methoxy)-, (6S)-
5H-Imidazo[2,1-b][1,3]oxazine, 6,7-dihydro-2-nitro-6-[[4-(trifluoromethoxy)phenyl]methoxy]-, (6S)- [ACD/Index Name]
9871
PA824
More...

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

PA 824 [DBID] [Wiki]
PA-824 [DBID]
AIDS007331 [DBID]
AIDS-007331 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Bio Activity:

      Antibacterial MedChem Express HY-10844
      Anti-infection MedChem Express HY-10844
      Anti-infection; MedChem Express HY-10844
      PA-824(Pretomanid) is a small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis; the MIC values of PA-824 against a panel of MTB pan-sensitive and rifampin mono-resistant cli nical isolates ranged from 0.015 to 0.25 ug/ml. MedChem Express
      PA-824(Pretomanid) is a small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis; the MIC values of PA-824 against a panel of MTB pan-sensitive and rifampin mono-resistant clinical isolates ranged from 0.015 to 0.25 ug/ml.; IC50 value: 0.015 to 0.25 ug/ml (MICs) [1]; Target: tuberculosis; PA-824 exhibited a sub-micromolar minimal inhibitory concentration (MIC) against MTB, Although PA-824 was not the most potent NAP against cultured MTB clinical isolates, it was the most active in infected mice when orally administered at 25 mg kg -1. MedChem Express HY-10844
      PA-824(Pretomanid) is a small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis; the MIC values of PA-824 against a panel of MTB pan-sensitive and rifampin mono-resistant clinical isolates ranged from 0.015 to 0.25 ug/ml.;IC50 value: 0.015 to 0.25 ug/ml (MICs) [1];Target: tuberculosisPA-824 exhibited a sub-micromolar minimal inhibitory concentration (MIC) against MTB, Although PA-824 was not the most potent NAP against cultured MTB clinical isolates, it was the most active in infected mice when orally administered at 25 mg kg -1. This indicated that PA-824 might possess more desirable pharmacokinetic properties than the other more potent NAP compounds that we tested. Further studies in mice at 25, 50 and 100 mg kg-1 PA-824 daily for 10 days resulted in reductions of mycobacterial burden in both spleen and lung tissues that were comparable to that of INH at 25 mg kg -1 [1]. PA-824 showed significant activity at 2, 10, and 50 microg/ml, similar to that of m MedChem Express HY-10844

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

Density: 1.6±0.1 g/cm3
Boiling Point: 462.3±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 72.3±3.0 kJ/mol
Flash Point: 233.4±31.5 °C
Index of Refraction: 1.589
Molar Refractivity: 76.4±0.5 cm3
#H bond acceptors: 8
#H bond donors: 0
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 2.70
ACD/LogD (pH 5.5): 2.31
ACD/BCF (pH 5.5): 33.69
ACD/KOC (pH 5.5): 431.47
ACD/LogD (pH 7.4): 2.31
ACD/BCF (pH 7.4): 33.69
ACD/KOC (pH 7.4): 431.47
Polar Surface Area: 91 Å2
Polarizability: 30.3±0.5 10-24cm3
Surface Tension: 49.9±7.0 dyne/cm
Molar Volume: 226.8±7.0 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) =  3.69

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  454.90  (Adapted Stein & Brown method)
    Melting Pt (deg C):  191.53  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.65E-009  (Modified Grain method)
    Subcooled liquid VP: 3.71E-007 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):  1.553
       log Kow used: 3.69 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  17.566 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.82E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.024E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.69  (KowWin est)
  Log Kaw used:  -9.705  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.395
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.3325
   Biowin2 (Non-Linear Model)     :   0.0001
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5978  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.0911  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0629
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0357
 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):  4.95E-005 Pa (3.71E-007 mm Hg)
  Log Koa (Koawin est  ): 13.395
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0606 
       Octanol/air (Koa) model:  6.1 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.687 
       Mackay model           :  0.829 
       Octanol/air (Koa) model:  0.998 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  60.6774 E-12 cm3/molecule-sec
      Half-Life =     0.176 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.115 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.758 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  562
      Log Koc:  2.750 

 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 = 2.144 (BCF = 139.5)
       log Kow used: 3.69 (estimated)

 Volatilization from Water:
    Henry LC:  4.82E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.302E+008  hours   (9.593E+006 days)
    Half-Life from Model Lake : 2.512E+009  hours   (1.047E+008 days)

 Removal In Wastewater Treatment:
    Total removal:              18.13  percent
    Total biodegradation:        0.22  percent
    Total sludge adsorption:    17.90  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       3.4e-005        4.23         1000       
   Water     4.44            4.32e+003    1000       
   Soil      94.7            8.64e+003    1000       
   Sediment  0.821           3.89e+004    0          
     Persistence Time: 7.82e+003 hr




                    

Click to predict properties on the Chemicalize site





Feedback Form