ChemSpider 2D Image | pyrazinamide | C5H5N3O

pyrazinamide

  • Molecular FormulaC5H5N3O
  • Average mass123.113 Da
  • Monoisotopic mass123.043259 Da
  • ChemSpider ID1017

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

2-(Aminocarbonyl)pyrazine
2-Pyrazincarboxamid [German] [ACD/IUPAC Name]
2-Pyrazinecarboxamide [ACD/Index Name] [ACD/IUPAC Name]
2-Pyrazinecarboxamide [French] [ACD/Index Name] [ACD/IUPAC Name]
5-25-04-00178 [Beilstein]
5-25-04-00178 (Beilstein Handbook Reference) [Beilstein]
98-96-4 [RN]
a-Pyrazinamide
Pirazinamida [Spanish] [INN]
Pyrazin-2-carboxamid [German]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

D 50 [DBID]
82612_FLUKA [DBID]
AC-907/25014068 [DBID]
AIDS007697 [DBID]
AIDS-007697 [DBID]
AIDS032294 [DBID]
AIDS-032294 [DBID]
BRN 0112306 [DBID]
C01956 [DBID]
CCRIS 545 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      WHITE POWDER NIH Clinical Collection [SMR000036662]
    • Safety:

      IRRITANT Matrix Scientific 085417
      Irritant SynQuest 4H48-1-2W
      None LKT Labs [P9671]
      P261; P262 Biosynth W-100059
    • Target Organs:

      FASI inhibitor TargetMol T1426
    • Compound Source:

      synthetic Microsource [01500518]
    • Bio Activity:

      Antibacterial MedChem Express HY-B0271
      Anti-infection MedChem Express HY-B0271
      Anti-infection; MedChem Express HY-B0271
      Enzyme TargetMol T1426
      FASI TargetMol T1426
      Pyrazinamide is a pyrazine that is used therapeutically as an antitubercular agent. MedChem Express
      Pyrazinamide is a pyrazine that is used therapeutically as an antitubercular agent.; Target: Antibacterial; Pyrazinamide is a prodrug that stops the growth of Mycobacterium tuberculosis. MedChem Express HY-B0271
      Pyrazinamide is a pyrazine that is used therapeutically as an antitubercular agent.;Target: AntibacterialPyrazinamide is a prodrug that stops the growth of Mycobacterium tuberculosis. Pyrazinoic acid was thought to inhibit the enzyme fatty acid synthase (FAS) I, which is required by the bacterium to synthesise fatty acids although this has been discounted. It was also suggested that the accumulation of pyrazinoic acid disrupts membrane potential and interferes with energy production, necessary for survival of M. tuberculosis at an acidic site of infection. Pyrazinoic acid binds to the ribosomal protein S1 (RpsA) and inhibits trans-translation. This may explain the ability of the drug to kill dormant mycobacteria [1-4]. MedChem Express HY-B0271
  • Gas Chromatography

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

Density: 1.3±0.1 g/cm3
Boiling Point: 357.4±22.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.8 mmHg at 25°C
Enthalpy of Vaporization: 60.3±3.0 kJ/mol
Flash Point: 169.9±22.3 °C
Index of Refraction: 1.577
Molar Refractivity: 31.4±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: -0.37
ACD/LogD (pH 5.5): -0.27
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 17.08
ACD/LogD (pH 7.4): -0.27
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 17.08
Polar Surface Area: 69 Å2
Polarizability: 12.4±0.5 10-24cm3
Surface Tension: 66.4±3.0 dyne/cm
Molar Volume: 94.6±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) =  -0.53
    Log Kow (Exper. database match) =  -0.60
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  304.40  (Adapted Stein & Brown method)
    Melting Pt (deg C):  106.77  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.73E-005  (Modified Grain method)
    MP  (exp database):  192 deg C
    Subcooled liquid VP: 0.00154 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):  1.558e+004
       log Kow used: -0.60 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1.5e+004 mg/L (25 deg C)
        Exper. Ref:  MERCK INDEX (1996)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L
    Wat Sol (Exper. database match) =  15000.00
       Exper. Ref:  MERCK INDEX (1996)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.20E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.839E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.60  (exp database)
  Log Kaw used:  -10.309  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.709
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8991
   Biowin2 (Non-Linear Model)     :   0.9811
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8729  (weeks       )
   Biowin4 (Primary Survey Model) :   3.8755  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4972
   Biowin6 (MITI Non-Linear Model):   0.5542
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0181
 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):  0.205 Pa (0.00154 mm Hg)
  Log Koa (Koawin est  ): 9.709
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.46E-005 
       Octanol/air (Koa) model:  0.00126 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.000527 
       Mackay model           :  0.00117 
       Octanol/air (Koa) model:  0.0913 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   2.2097 E-12 cm3/molecule-sec
      Half-Life =     4.841 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    58.087 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.000847 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5.589
      Log Koc:  0.747 

 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: -0.60 (expkow database)

 Volatilization from Water:
    Henry LC:  1.2E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.414E+008  hours   (2.256E+007 days)
    Half-Life from Model Lake : 5.906E+009  hours   (2.461E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       2.84e-005       116          1000       
   Water     38.9            360          1000       
   Soil      61.1            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 580 hr




                    

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