ChemSpider 2D Image | ethionamide | C8H10N2S

ethionamide

  • Molecular FormulaC8H10N2S
  • Average mass166.243 Da
  • Monoisotopic mass166.056473 Da
  • ChemSpider ID2041901

More details:



Featured data source



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

208-628-9 [EINECS]
2-Ethyl-4-pyridincarbimidothiosäure [German] [ACD/IUPAC Name]
2-Ethyl-4-pyridincarbothioamid [German] [ACD/IUPAC Name]
2-Ethyl-4-pyridinecarbimidothioic acid [ACD/IUPAC Name]
2-Ethyl-4-pyridinecarbothioamide [ACD/IUPAC Name]
2-Éthyl-4-pyridinecarbothioamide [French] [ACD/IUPAC Name]
2-Ethyl-4-thioamidylpyridine
2-Ethylpyridin-4-carbothioamid
2-Ethylpyridine-4-carbothioamide
2-éthylpyridine-4-carbothioamide [French]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

OAY8ORS3CQ [DBID]
AIDS007656 [DBID]
AIDS-007656 [DBID]
AIDS032283 [DBID]
AIDS-032283 [DBID]
Bayer 5312 [DBID]
BRN 0116474 [DBID]
C07665 [DBID]
CCRIS 287 [DBID]
D00591 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      YELLOW POWDER NIH Clinical Collection [SMR001370750]
    • Safety:

      GHS07; GHS08 Biosynth W-105719
      H302; H361 Biosynth W-105719
      IRRITANT Matrix Scientific 085028
      J04AD03 Wikidata Q414767
      P281 Biosynth W-105719
      Warning Biosynth W-105719
    • Target Organs:

      Catalase-peroxidase;Reductase TargetMol T1165
    • Chemical Class:

      A thiocarboxamide that is pyridine-4-carbothioamide substituted by an ethyl group at position 2. A prodrug that undergoes metabolic activation by conversion to the corresponding <element>S</element>-o xide. ChEBI CHEBI:4885
    • Compound Source:

      synthetic Microsource [01500292]
    • Bio Activity:

      Antibacterial MedChem Express HY-B0276
      Anti-infection MedChem Express HY-B0276
      Anti-infection; MedChem Express HY-B0276
      Catalase-peroxidase;NAPDH TargetMol T1165
      Enzyme TargetMol T1165
      Ethionamide(2-ethylthioisonicotinamide) is an antibiotic used in the treatment of tuberculosis. MedChem Express
      Ethionamide(2-ethylthioisonicotinamide) is an antibiotic used in the treatment of tuberculosis.; Target: Antibacterial; Ethionamide is a second-line antitubercular agent that inhibits mycolic acid synthesis. MedChem Express HY-B0276
      Ethionamide(2-ethylthioisonicotinamide) is an antibiotic used in the treatment of tuberculosis.;Target: AntibacterialEthionamide is a second-line antitubercular agent that inhibits mycolic acid synthesis. It also may be used for treatment of leprosy. Ethionamide is a prodrug. It is activated by the enzyme EthA, a mono-oxygenase in Mycobacterium tuberculosis, and binds NAD+ to form an adduct which inhibits InhA in the same way as isoniazid. Expression of the ethA gene is controlled by EthR, a transcriptional repressor. It is understood that improving ethA expression will increase the efficacy of ethionamide and so EthR inhibitors are of great interest to co-drug developers. The action may be through disruption of mycolic acid [1, 2]. MedChem Express HY-B0276
  • Gas Chromatography
    • Retention Index (Kovats):

      1629 (estimated with error: 89) NIST Spectra mainlib_290504, replib_248283, replib_251351
    • Retention Index (Normal Alkane):

      1756 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 536334; Active phase: Methyl Silicone; Data type: Normal alkane RI; Authors: Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 220, 1981, 195-252.) NIST Spectra nist ri
    • Retention Index (Linear):

      1720 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 1.8 m; Column type: Packed; Heat rate: 8 K/min; Start T: 130 C; End T: 290 C; End time: 8 min; Start time: 2 min; CAS no: 536334; Active phase: SE-30; Carrier gas: N2; Substrate: Chromosorb W; Data type: Linear RI; Authors: Perrigo, B.J.; Peel, H.W., The use of retention indices and temperature-programmed gas chromatography in analytical toxicology, J. Chromatogr. Sci., 19, 1981, 219-226.) NIST Spectra nist ri

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

Density: 1.2±0.1 g/cm3
Boiling Point: 296.6±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.6 mmHg at 25°C
Enthalpy of Vaporization: 53.6±3.0 kJ/mol
Flash Point: 133.2±27.9 °C
Index of Refraction: 1.623
Molar Refractivity: 50.1±0.3 cm3
#H bond acceptors: 2
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 1.22
ACD/LogD (pH 5.5): 1.42
ACD/BCF (pH 5.5): 7.09
ACD/KOC (pH 5.5): 140.83
ACD/LogD (pH 7.4): 1.43
ACD/BCF (pH 7.4): 7.19
ACD/KOC (pH 7.4): 142.90
Polar Surface Area: 71 Å2
Polarizability: 19.9±0.5 10-24cm3
Surface Tension: 59.2±3.0 dyne/cm
Molar Volume: 142.0±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) =  1.52

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  288.95  (Adapted Stein & Brown method)
    Melting Pt (deg C):  86.10  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.000134  (Modified Grain method)
    MP  (exp database):  163 deg C
    Subcooled liquid VP: 0.0035 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):  3.258e+004
       log Kow used: 1.52 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2.933e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.51E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.997E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.52  (KowWin est)
  Log Kaw used:  -7.513  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.033
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7787
   Biowin2 (Non-Linear Model)     :   0.9071
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4886  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7261  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2801
   Biowin6 (MITI Non-Linear Model):   0.1691
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4216
 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):  0.467 Pa (0.0035 mm Hg)
  Log Koa (Koawin est  ): 9.033
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6.43E-006 
       Octanol/air (Koa) model:  0.000265 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.000232 
       Mackay model           :  0.000514 
       Octanol/air (Koa) model:  0.0207 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  24.1268 E-12 cm3/molecule-sec
      Half-Life =     0.443 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     5.320 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.000373 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  203
      Log Koc:  2.308 

 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 = 0.474 (BCF = 2.975)
       log Kow used: 1.52 (estimated)

 Volatilization from Water:
    Henry LC:  7.51E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.005E+006  hours   (4.188E+004 days)
    Half-Life from Model Lake : 1.097E+007  hours   (4.569E+005 days)

 Removal In Wastewater Treatment:
    Total removal:               1.98  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.89  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       0.00847         10.6         1000       
   Water     32.6            900          1000       
   Soil      67.3            1.8e+003     1000       
   Sediment  0.0834          8.1e+003     0          
     Persistence Time: 1.19e+003 hr




                    

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