ChemSpider 2D Image | Zileuton | C11H12N2O2S

Zileuton

  • Molecular FormulaC11H12N2O2S
  • Average mass236.290 Da
  • Monoisotopic mass236.061951 Da
  • ChemSpider ID54531

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

(±)-N-hydroxy-N-(1-benzo[b]thien-2-ylethyl)urea
1-[1-(1-Benzothiophen-2-yl)ethyl]-1-hydroxyharnstoff [German] [ACD/IUPAC Name]
1-[1-(1-Benzothiophen-2-yl)ethyl]-1-hydroxyurea [ACD/IUPAC Name]
1-[1-(1-Benzothiophén-2-yl)éthyl]-1-hydroxyurée [French] [ACD/IUPAC Name]
111406-87-2 [RN]
6595
Leutrol [Trade name]
MFCD00866097 [MDL number]
UNII:V1L22WVE2S
Urea, N-(1-benzo[b]thien-2-ylethyl)-N-hydroxy- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

0CG9649AC6 [DBID]
8POY3UMU73 [DBID]
A 64077 [DBID]
A-64077 [DBID]
ABT-077 [DBID]
CHEBI:10112 [DBID]
CTI-02 [DBID]
D00414 [DBID]
LS-158908 [DBID]
Prestwick0_001090 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      22-36 LKT Labs [Z3444]
      H302 H319 LKT Labs [Z3444]
      None LKT Labs [Z3444]
      Xn LKT Labs [Z3444]
    • Target Organs:

      5-Lipoxygenase inhibitor; COX inhibitor TargetMol T0477
    • Chemical Class:

      A member of the class of 1-benzothiophenes that is 1-benzothiophene in which the hydrogen at position 2 is replaced by a 1-[carbamoyl(hydroxy)amino]ethyl group. A selective 5-lipoxygenase inhibitor, i t inhibits the formation of leukotrienes LTB4, LTC4, LDT4, and LTE4. It is used for the management of chronic asthma. ChEBI CHEBI:10112
    • Therapeutical Effect:

      5-lipoxygenase inhibitor Rudolf Boehm Institute [01505906]
    • Drug Status:

      approved BIONET-Key Organics KS-1195
    • Compound Source:

      synthetic; Abbott-64077 Rudolf Boehm Institute [01505906]
    • Bio Activity:

      5-Lipoxygenase MedChem Express HY-14164
      5-Lipoxygenase;Prostaglandin G/H synthase 1 TargetMol T0477
      5-LOX inhibitor; orally bioavailable Tocris Bioscience 3308
      Enzymes Tocris Bioscience 3308
      Lipoxygenase Tocris Bioscience 3308
      Metabolism/Protease MedChem Express HY-14164
      Metabolism/Protease; MedChem Express HY-14164
      Metabolism; Neuroscience TargetMol T0477
      Orally active 5-lipoxygenase (5-LOX) inhibitor that inhibits LTB4 synthesis (IC50 values are 0.56, 2.3 and 2.6 ?M in dog, rat and human blood respectively). Inhibits antigen-induced contraction of tra cheal strips in vitro (IC50 = 6 ?M) and exhibits antiasthmatic activity in vivo. Also weakly inhibits CYP1A2 (Ki = 66 - 98 ?M). Tocris Bioscience 3308
      Orally active 5-lipoxygenase (5-LOX) inhibitor that inhibits LTB4 synthesis (IC50 values are 0.56, 2.3 and 2.6 ?M in dog, rat and human blood respectively). Inhibits antigen-induced contraction of tracheal strips in vitro (IC50 = 6 ?M) and exhibits antiasthmatic activity in vivo. Also weakly inhibits CYP1A2 (Ki = 66 - 98 ?M). Tocris Bioscience 3308
      Orally active 5-lipoxygenase (5-LOX) inhibitor that inhibits LTB4 synthesis (IC50 values are 0.56, 2.3 and 2.6 muM in dog, rat and human blood respectively). Inhibits antigen-induced contraction of tracheal strips in vitro (IC50 = 6 muM) and exhibits antiasthmatic activity in vivo. Also weakly inhibits CYP1A2 (Ki = 66 - 98 muM). Tocris Bioscience 3308
      Orally active 5-LOX inhibitor Tocris Bioscience 3308
      Oxygenases/Oxidases Tocris Bioscience 3308
      Zileuton (A-64077) is a selective and potent 5-LO inhibitor, and thus inhibits leukotrienes (LTB4, LTC4, LTD4, and LTE4) formation.; IC50 Value: ; Target: 5-lipoxygenase; in vitro: Zileuton inhibited 5-hydroxyeicosatetraenoic acid synthesis by rat basophilic leukemia cell 20,000 x g supernatant and rat polymorphonuclear leukocytes (PMNL) (IC50 = 0.5 and 0.3 microM) respectively. MedChem Express HY-14164
      Zileuton (A-64077) is a selective and potent 5-LO inhibitor, and thus inhibits leukotrienes (LTB4, LTC4, LTD4, and LTE4) formation.;IC50 Value: ;Target: 5-lipoxygenase;In vitro: Zileuton inhibited 5-hydroxyeicosatetraenoic acid synthesis by rat basophilic leukemia cell 20,000 x g supernatant and rat polymorphonuclear leukocytes (PMNL) (IC50 = 0.5 and 0.3 microM) respectively. It also inhibited leukotriene (LT)B4 biosynthesis by rat PMNL (IC50 = 0.4 microM), human PMNL (IC50 = 0.4 microM) and human whole blood (IC50 = 0.9 microM) [1]. Zileuton inhibited antigen-induced contractions of guinea-pig tracheal strips (GPTS) from actively sensitized animals with an IC50of 6 microM [1].;In vivo: Additionally, while total tau levels were unchanged for both groups, zileuton-treated mice had a significant reduction in its phosphorylation state and insoluble forms, secondary to a decreased activation of the cdk5 kinase [2]. Neurological deficit scores, infarct volume, and neuronal damage were MedChem Express HY-14164

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

Density: 1.4±0.1 g/cm3
Boiling Point: 449.4±47.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 74.6±3.0 kJ/mol
Flash Point: 225.6±29.3 °C
Index of Refraction: 1.704
Molar Refractivity: 65.5±0.3 cm3
#H bond acceptors: 4
#H bond donors: 3
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 3.74
ACD/LogD (pH 5.5): 2.49
ACD/BCF (pH 5.5): 46.30
ACD/KOC (pH 5.5): 541.79
ACD/LogD (pH 7.4): 2.49
ACD/BCF (pH 7.4): 45.90
ACD/KOC (pH 7.4): 537.06
Polar Surface Area: 95 Å2
Polarizability: 26.0±0.5 10-24cm3
Surface Tension: 68.8±3.0 dyne/cm
Molar Volume: 168.7±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) =  2.59

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  441.69  (Adapted Stein & Brown method)
    Melting Pt (deg C):  185.36  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.28E-010  (Modified Grain method)
    Subcooled liquid VP: 1.08E-008 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):  171.6
       log Kow used: 2.59 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  745.49 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.76E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.131E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.59  (KowWin est)
  Log Kaw used:  -10.559  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.149
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6351
   Biowin2 (Non-Linear Model)     :   0.4142
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6770  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5068  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0409
   Biowin6 (MITI Non-Linear Model):   0.0319
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.3124
 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):  1.44E-006 Pa (1.08E-008 mm Hg)
  Log Koa (Koawin est  ): 13.149
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.08 
       Octanol/air (Koa) model:  3.46 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.987 
       Mackay model           :  0.994 
       Octanol/air (Koa) model:  0.996 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  81.2953 E-12 cm3/molecule-sec
      Half-Life =     0.132 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.579 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.99 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4111
      Log Koc:  3.614 

 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 = 1.297 (BCF = 19.81)
       log Kow used: 2.59 (estimated)

 Volatilization from Water:
    Henry LC:  6.76E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.331E+009  hours   (5.547E+007 days)
    Half-Life from Model Lake : 1.452E+010  hours   (6.052E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               3.38  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     3.27  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       0.000565        3.16         1000       
   Water     15.3            900          1000       
   Soil      84.6            1.8e+003     1000       
   Sediment  0.148           8.1e+003     0          
     Persistence Time: 1.67e+003 hr




                    

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