ChemSpider 2D Image | Glibenclamide | C23H28ClN3O5S

Glibenclamide

  • Molecular FormulaC23H28ClN3O5S
  • Average mass494.004 Da
  • Monoisotopic mass493.143829 Da
  • ChemSpider ID3368

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Glibenclamide [INN] [JP15] [Wiki]
10238-21-8 [RN]
5-Chlor-N-(2-{4-[(cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-2-methoxybenzamid [German] [ACD/IUPAC Name]
5-Chlor-N-(2-{4-[(cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-2-methoxybenzolcarboxamid [German]
5-Chlor-N-[2-(4-{[(E)-(cyclohexylimino)(hydroxy)methyl]sulfamoyl}phenyl)ethyl]-2-methoxybenzolcarboximidsäure [German] [ACD/IUPAC Name]
5-Chloro-N-(2-{4-[(cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-2-methoxybenzamide [ACD/IUPAC Name]
5-Chloro-N-(2-{4-[(cyclohexylcarbamoyl)sulfamoyl]phényl}éthyl)-2-méthoxybenzamide [French] [ACD/IUPAC Name]
5-Chloro-N-[2-(4-{[(E)-(cyclohexylimino)(hydroxy)methyl]sulfamoyl}phenyl)ethyl]-2-methoxybenzenecarboximidic acid [ACD/IUPAC Name]
Acide 5-chloro-N-[2-(4-{[(E)-(cyclohexylimino)(hydroxy)méthyl]sulfamoyl}phényl)éthyl]-2-méthoxybenzènecarboximidique [French] [ACD/IUPAC Name]
Benzamide, 5-chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxy- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Bio1_000076 [DBID]
Bio1_000565 [DBID]
Bio1_001054 [DBID]
Bio2_000071 [DBID]
Bio2_000551 [DBID]
BRN 2230085 [DBID]
C07022 [DBID]
CBiol_001790 [DBID]
CHEBI:5441 [DBID]
D00336 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      WHITE POWDER NIH Clinical Collection [SMR000058229]
      white solid Oxford University Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable. Oxford University Chemical Safety Data (No longer updated) More details
    • Toxicity:

      ORL-RAT LD50 > 20000 mg kg-1, IPN-RAT LD50 3750 mg kg-1, ORL-MUS LD50 3250 mg kg-1 Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      IRRITANT Matrix Scientific 093683
      Safety glasses, gloves, good ventilation. Oxford University Chemical Safety Data (No longer updated) More details
      WARNING: Irreversible damage risk, protect skin/eyes/lungs. Alfa Aesar B21459
    • Target Organs:

      Potassium Channel inhibitor TargetMol T1634
    • Drug Status:

      Approved BIONET-Key Organics KS-5326
      USP, INN, BAN, JAN Microsource [02300229]
    • Compound Source:

      synthetic Microsource [02300229]
    • Bio Activity:

      ATP-dependent K+ channel (Kir6, KATP) and CFTR Cl- channel blocker. Inhibits Kir6 currents in the pancreas, causing an increase in intracellular Ca2+ and insulin secretion. Inhibits recombinant CFTR C l- channels with an IC50 of 20 ?M. Tocris Bioscience 0911
      ATP-dependent K+ channel (Kir6, KATP) and CFTR Cl- channel blocker. Inhibits Kir6 currents in the pancreas, causing an increase in intracellular Ca2+ and insulin secretion. Inhibits recombinant CFTR Cl- channels with an IC50 of 20 ?M. Tocris Bioscience 911
      ATP-dependent K+ channel (Kir6, KATP) and CFTR Cl- channel blocker. Inhibits Kir6 currents in the pancreas, causing an increase in intracellular Ca2+ and insulin secretion. Inhibits recombinant CFTR Cl- channels with an IC50 of 20 muM. Tocris Bioscience 911
      Glibenclamide(Glyburide) is a sulfonylurea compound that modulates insulin production. MedChem Express http://www.medchemexpress.com/armodafinil.html, HY-15206
      Glibenclamide(Glyburide) is a sulfonylurea compound that modulates insulin production. ;IC50 value:;Target:Sulfonylureas bind to ATP-dependent K+ channels in beta cells of the pancreas, depolarizing them and stimulating the release of Ca2+, which in turn stimulates insulin production. Glibenclamide, a sulphonylurea oral hypoglycaemic agent is a widely used antagonist of cromakalim-activated K+ channels in smooth muscle. Binding of Gli to SUR produces the closure of KATP channels and the inhibition of their activity. Glibenclamide is widely used for treatment of type 2-diabetes and it has been signaled as antiproliferative in several tumor cell lines. MedChem Express HY-15206
      Inhibits drug-induced coronary vasodilation; Antidiabetic drug Zerenex Molecular [ZBioX-0147]
      Inward rectifier Potassium Channels Tocris Bioscience 911
      Ion Channels Tocris Bioscience 911
      Kir6 (KATP) channel blocker Tocris Bioscience 0911, 911
      Membrane Tranporter/Ion Channel MedChem Express HY-15206
      Membrane Tranporter/Ion Channel; MedChem Express HY-15206
      Membrane Transporter/Ion Channel TargetMol T1634
      Potassium Channel;Bile salt export pump TargetMol T1634
      Potassium Channels Tocris Bioscience 911
      Potassiun Channel MedChem Express HY-15206
  • Gas Chromatography
    • Retention Index (Kovats):

      4313 (estimated with error: 89) NIST Spectra mainlib_247159, replib_107102
    • Retention Index (Normal Alkane):

      3531 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.25 mm; Column length: 15 m; Column type: Capillary; Heat rate: 10 K/min; Start T: 130 C; End T: 290 C; End time: 10 min; Start time: 1 min; CAS no: 10238218; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Sharp, M.E., A rapid screening procedure for acidic and neutral drugs in blood by high resolution gas chromatography, J. Anal. Toxicol., 11, 1987, 8-11.) NIST Spectra nist ri

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

Density: 1.4±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.616
Molar Refractivity: 126.9±0.4 cm3
#H bond acceptors: 8
#H bond donors: 3
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 3.75
ACD/LogD (pH 5.5): 2.87
ACD/BCF (pH 5.5): 53.83
ACD/KOC (pH 5.5): 331.36
ACD/LogD (pH 7.4): 1.85
ACD/BCF (pH 7.4): 5.14
ACD/KOC (pH 7.4): 31.62
Polar Surface Area: 122 Å2
Polarizability: 50.3±0.5 10-24cm3
Surface Tension: 61.3±5.0 dyne/cm
Molar Volume: 362.9±5.0 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) =  4.79

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  708.87  (Adapted Stein & Brown method)
    Melting Pt (deg C):  310.17  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.15E-015  (Modified Grain method)
    MP  (exp database):  169 deg C
    Subcooled liquid VP: 9.65E-014 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):  0.06346
       log Kow used: 4.79 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  4 mg/L (27 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.068292 mg/L
    Wat Sol (Exper. database match) =  4.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.56E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.227E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.79  (KowWin est)
  Log Kaw used:  -16.510  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  21.300
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7267
   Biowin2 (Non-Linear Model)     :   0.3764
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7137  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.1837  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2668
   Biowin6 (MITI Non-Linear Model):   0.0005
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.3600
 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):  1.29E-011 Pa (9.65E-014 mm Hg)
  Log Koa (Koawin est  ): 21.300
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.33E+005 
       Octanol/air (Koa) model:  4.9E+008 
   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 =  40.0468 E-12 cm3/molecule-sec
      Half-Life =     0.267 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.205 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  2.525E+004
      Log Koc:  4.402 

 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 = 2.988 (BCF = 973.8)
       log Kow used: 4.79 (estimated)

 Volatilization from Water:
    Henry LC:  7.56E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.721E+015  hours   (7.172E+013 days)
    Half-Life from Model Lake : 1.878E+016  hours   (7.824E+014 days)

 Removal In Wastewater Treatment:
    Total removal:              69.95  percent
    Total biodegradation:        0.62  percent
    Total sludge adsorption:    69.33  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       4.94e-007       6.41         1000       
   Water     3.23            4.32e+003    1000       
   Soil      87              8.64e+003    1000       
   Sediment  9.74            3.89e+004    0          
     Persistence Time: 9.01e+003 hr




                    

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