ChemSpider 2D Image | ezetimibe | C24H21F2NO3

ezetimibe

  • Molecular FormulaC24H21F2NO3
  • Average mass409.425 Da
  • Monoisotopic mass409.148956 Da
  • ChemSpider ID132493
  • defined stereocentres - 3 of 3 defined stereocentres


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

(3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinone [ACD/IUPAC Name]
(3R,4S)-1-(4-Fluorophényl)-3-[(3S)-3-(4-fluorophényl)-3-hydroxypropyl]-4-(4-hydroxyphényl)-2-azétidinone [French] [ACD/IUPAC Name]
(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one
(3R,4S)-1-(4-fluorophényl)-3-[(3S)-3-(4-fluorophényl)-3-hydroxypropyl]-4-(4-hydroxyphényl)azétidin-2-one
(3R,4S)-1-(4-Fluorphenyl)-3-[(3S)-3-(4-fluorphenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinon [German] [ACD/IUPAC Name]
(3R,4S)-1-(4-Fluorphenyl)-3-[(3S)-3-(4-fluorphenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-on
2-Azetidinone, 1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-, (3R,4S)- [ACD/Index Name]
ezetimiba [Spanish] [INN]
ézétimibe [French] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

D01966 [DBID]
LS-181801 [DBID]
MK-0653 [DBID]
SCH 58235 [DBID]
SCH-58235 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      GHS07 Biosynth Q-201106
      H315; H319; H335 Biosynth Q-201106
      P261; P280; P302+P352; P304+P340; P305+P351+P338; P312 Biosynth Q-201106
      Warning Biosynth Q-201106
    • Target Organs:

      Cholesterol transport inhibitor;NPC1L1 inhibitor;APN TargetMol T1593
    • Chemical Class:

      A <locant>beta</locant>-lactam that is azetidin-2-one which is substituted at 1, 3, and 4 by <ital>p</ital>-fluorophenyl, 3-(<ital>p</ital>-fluorophenyl)-3-hydroxypropyl, and 4-hydroxyphenyl groups, respectively (the 3<stereo>R</stereo>,3'<stereo>S</stereo>,4<stereo>S</stereo> enantiomer). ChEBI CHEBI:49040
    • Drug Status:

      approved BIONET-Key Organics KS-1170
    • Bio Activity:

      Ezetimibe, a cholesterol-absorption inhibitor, reduces levels of low-density lipoprotein (LDL) cholesterol when added to statin treatment. MedChem Express http://www.medchemexpress.com/rivastigmine.html, HY-17376
      Ezetimibe, a cholesterol-absorption inhibitor, reduces levels of low-density lipoprotein (LDL) cholesterol when added to statin treatment. ;IC50 value:;Target: cholesterol-absorptionEzetimibe is a lipid-lowering drug that inhibits the intestinal absorption of dietary and biliary cholesterol by blocking passage across the intestinal wall. In patients with familial hypercholesterolemia, combined therapy with ezetimibe and simvastatin did not result in a significant difference in changes in intima-media thickness, as compared with simvastatin alone, despite decreases in levels of LDL cholesterol and C-reactive protein. (ClinicalTrials.gov number, NCT00552097.) Ezetimibe offers a new therapeutic option for patients receiving statins who require further reduction in LDL cholesterol. MedChem Express HY-17376
      Metabolism TargetMol T1593
      Others MedChem Express HY-17376
      Sterol O-acyltransferase;NPC1L1;APN TargetMol T1593

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

Density: 1.3±0.1 g/cm3
Boiling Point: 654.9±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 101.3±3.0 kJ/mol
Flash Point: 349.9±31.5 °C
Index of Refraction: 1.624
Molar Refractivity: 108.3±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 3.26
ACD/LogD (pH 5.5): 3.68
ACD/BCF (pH 5.5): 366.41
ACD/KOC (pH 5.5): 2381.67
ACD/LogD (pH 7.4): 3.67
ACD/BCF (pH 7.4): 364.57
ACD/KOC (pH 7.4): 2369.71
Polar Surface Area: 61 Å2
Polarizability: 42.9±0.5 10-24cm3
Surface Tension: 54.8±3.0 dyne/cm
Molar Volume: 306.8±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) =  3.94

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  557.84  (Adapted Stein & Brown method)
    Melting Pt (deg C):  239.62  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.47E-014  (Modified Grain method)
    Subcooled liquid VP: 3.07E-012 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):  4.406
       log Kow used: 3.94 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  37.803 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.41E-018  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.797E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.94  (KowWin est)
  Log Kaw used:  -15.744  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.684
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.5827
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.6426  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.6585  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0712
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5059
 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):  4.09E-010 Pa (3.07E-012 mm Hg)
  Log Koa (Koawin est  ): 19.684
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  7.33E+003 
       Octanol/air (Koa) model:  1.19E+007 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  71.0626 E-12 cm3/molecule-sec
      Half-Life =     0.151 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.806 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.168E+005
      Log Koc:  5.067 

 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 = 1.683 (BCF = 48.16)
       log Kow used: 3.94 (estimated)

 Volatilization from Water:
    Henry LC:  4.41E-018 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.686E+014  hours   (1.119E+013 days)
    Half-Life from Model Lake : 2.931E+015  hours   (1.221E+014 days)

 Removal In Wastewater Treatment:
    Total removal:              27.40  percent
    Total biodegradation:        0.30  percent
    Total sludge adsorption:    27.10  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       3.44e-006       3.61         1000       
   Water     4.11            4.32e+003    1000       
   Soil      94.4            8.64e+003    1000       
   Sediment  1.5             3.89e+004    0          
     Persistence Time: 8.06e+003 hr




                    

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