ChemSpider 2D Image | Levamisole | C11H12N2S

Levamisole

  • Molecular FormulaC11H12N2S
  • Average mass204.291 Da
  • Monoisotopic mass204.072113 Da
  • ChemSpider ID25037
  • defined stereocentres - 1 of 1 defined stereocentres


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Levamisole [INN] [Wiki]
(-)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole(-)-Tetramisole
(-)-Tetramisole
(6S)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole
(6S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazol [German] [ACD/IUPAC Name]
(6S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole [ACD/IUPAC Name]
(6S)-6-Phényl-2,3,5,6-tétrahydroimidazo[2,1-b][1,3]thiazole [French] [ACD/IUPAC Name]
(S)-(-)-Levamisole
238-836-5 [EINECS]
Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, (S)-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS006754 [DBID]
AIDS-006754 [DBID]
C07070 [DBID]
DivK1c_000667 [DBID]
KBio1_000667 [DBID]
KBio2_002089 [DBID]
KBio2_004657 [DBID]
KBio2_007225 [DBID]
KBio3_001783 [DBID]
KBioGR_001436 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-<ital>b</ital>][1,3]thiazole that has <stereo>S</stereo> configuration. It is used (generally as the monohydrochloride salt) to treat parasitic worm infections in pigs, sheep and cattle and was formerly used in humans as an adjuvant to chemotherapy for the treatment of various cancers. It is also widely used as an adulterant to coccaine. ChEBI CHEBI:6432
    • Bio Activity:

      XC50_3D7 (uM) (Plasmodium Falciparum, Malaria): 0.622197874 GlaxoSmithKline Malaria Set

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

Density: 1.3±0.1 g/cm3
Boiling Point: 344.4±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.8 mmHg at 25°C
Enthalpy of Vaporization: 58.8±3.0 kJ/mol
Flash Point: 162.1±28.7 °C
Index of Refraction: 1.713
Molar Refractivity: 60.4±0.5 cm3
#H bond acceptors: 2
#H bond donors: 0
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 1.85
ACD/LogD (pH 5.5): 0.16
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 3.55
ACD/LogD (pH 7.4): 0.25
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 4.43
Polar Surface Area: 41 Å2
Polarizability: 23.9±0.5 10-24cm3
Surface Tension: 54.1±7.0 dyne/cm
Molar Volume: 154.1±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) =  2.87
    Log Kow (Exper. database match) =  1.84
       Exper. Ref:  BioByte (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  316.77  (Adapted Stein & Brown method)
    Melting Pt (deg C):  112.10  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.000111  (Modified Grain method)
    Subcooled liquid VP: 0.000797 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):  1116
       log Kow used: 1.84 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  565.39 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.03E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.674E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.84  (exp database)
  Log Kaw used:  -7.783  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.623
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7784
   Biowin2 (Non-Linear Model)     :   0.8707
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7697  (weeks       )
   Biowin4 (Primary Survey Model) :   3.5579  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1949
   Biowin6 (MITI Non-Linear Model):   0.1419
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2502
 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):  0.106 Pa (0.000797 mm Hg)
  Log Koa (Koawin est  ): 9.623
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.82E-005 
       Octanol/air (Koa) model:  0.00103 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00102 
       Mackay model           :  0.00225 
       Octanol/air (Koa) model:  0.0762 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  33.2636 E-12 cm3/molecule-sec
      Half-Life =     0.322 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.859 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.00164 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  8652
      Log Koc:  3.937 

 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 = 0.717 (BCF = 5.21)
       log Kow used: 1.84 (expkow database)

 Volatilization from Water:
    Henry LC:  4.03E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.077E+006  hours   (8.652E+004 days)
    Half-Life from Model Lake : 2.265E+007  hours   (9.439E+005 days)

 Removal In Wastewater Treatment:
    Total removal:               2.12  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     2.03  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       0.00788         7.72         1000       
   Water     24.8            360          1000       
   Soil      75.1            720          1000       
   Sediment  0.0747          3.24e+003    0          
     Persistence Time: 687 hr




                    

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