ChemSpider 2D Image | Bumetanide | C17H20N2O5S

Bumetanide

  • Molecular FormulaC17H20N2O5S
  • Average mass364.416 Da
  • Monoisotopic mass364.109283 Da
  • ChemSpider ID2377

More details:



Featured data source



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

0Y2S3XUQ5H
249-004-6 [EINECS]
28395-03-1 [RN]
2943
3-(aminosulfonyl)-5-(butylamino)-4-(phenyloxy)benzoic acid
3-(Butylamino)-4-phenoxy-5-sulfamoylbenzoesäure [German] [ACD/IUPAC Name]
3-(Butylamino)-4-phenoxy-5-sulfamoylbenzoic acid [ACD/IUPAC Name]
3-(Butylamino)-4-phenoxy-5-sulfamoylbenzolcarbonsäure [German]
Acide 3-(butylamino)-4-phénoxy-5-sulfamoylbenzoïque [French] [ACD/IUPAC Name]
Benzoic acid, 3-(aminosulfonyl)-5-(butylamino)-4-phenoxy- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

B3023_SIGMA [DBID]
Bio1_000421 [DBID]
Bio1_000910 [DBID]
Bio1_001399 [DBID]
Bio2_000228 [DBID]
Bio2_000708 [DBID]
BRN 2185351 [DBID]
CCRIS 4693 [DBID]
D00247 [DBID]
DivK1c_000034 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      Not Available Novochemy [NC-23201]
      WHITE POWDER NIH Clinical Collection [SMR000058418]
    • Safety:

      20/21/22 Novochemy [NC-23201]
      20/21/36/37/39 Novochemy [NC-23201]
      C03CA02 Wikidata Q275926
      GHS07; GHS09 Novochemy [NC-23201]
      H302, H311 LKT Labs [B8248]
      H332; H403 Novochemy [NC-23201]
      P301+P310; P337+P313 Novochemy [NC-23201]
      R22-23-24 LKT Labs [B8248]
      R52/53 Novochemy [NC-23201]
      Warning Novochemy [NC-23201]
      Xn, T LKT Labs [B8248]
    • Target Organs:

      NKCC cotransporter inhibitor TargetMol T0108
    • Chemical Class:

      A member of the class of benzoic acids that is 4-phenoxybenzoic acid in which the hydrogens <ital>ortho</ital> to the phenoxy group are substituted by butylamino and sulfamoyl groups. Bumetanide is a diuretic, and is used for treatment of oedema associated with congestive heart failure, hepatic and renal disease. ChEBI CHEBI:3213
    • Drug Status:

      approved BIONET-Key Organics KS-5211
    • Compound Source:

      synthetic Microsource [01502004]
    • Bio Activity:

      Bumetanide(Ro 10-6338; PF 1593) is an inhibitor of Na(+)-K(+)-2Cl(-) co-transporter (NKCC) with an IC50 of 0.6 uM. MedChem Express
      Bumetanide(Ro 10-6338; PF 1593) is an inhibitor of Na(+)-K(+)-2Cl(-) co-transporter (NKCC) with an IC50 of 0.6 uM.; IC50 Value: 0.6 uM [1]; Target: NKCC (Na-K-Cl cotransporter); in vitro: Cultured chick cardiac cells possess a Na+K+Cl-co-transport system that is inhibited by the loop diuretics bumetanide (IC50 = 0.6 microM). MedChem Express HY-17468
      Bumetanide(Ro 10-6338; PF 1593) is an inhibitor of Na(+)-K(+)-2Cl(-) co-transporter (NKCC) with an IC50 of 0.6 uM.;IC50 Value: 0.6 uM [1];Target: NKCC (Na-K-Cl cotransporter);In vitro: Cultured chick cardiac cells possess a Na+K+Cl-co-transport system that is inhibited by the loop diuretics bumetanide (IC50 = 0.6 microM). The K0.5 values for Cl- and Na+ activation of thebumetanide-sensitive 86Rb+ uptake are 59 mM and 40mM respectively. Bumetanide also inhibits a 22Na+ uptake component that is suppressed when external Cl- or K+ are substituted by impermeant ions. The ratio of bumetanide-sensitive 86Rb+ to 22Na+ uptake is close to 1. The cardiac Na+/K+/Cl- cotransport is a major uptake pathway for Na+ and K+ [1]. Bumetanide inhibits ouabain-resistant 86Rb(K+) influx with IC50of 0.1, 5.0, and 0.05 microM for J774.2, CT2 and J7H1 macrophages, respectively [2]. ;In vivo:Intraperitoneal injection of 50 or 100 mg bumetanide/kg body weight resulted in an acute and transient hyperglycaem MedChem Express HY-17468
      Ion Pumps/Transporters Tocris Bioscience 3108
      Loop diuretic that inhibits the Na+/2Cl-/K+ (NKCC) cotransporter. More potent than furosemide (Cat. No. 3109). Tocris Bioscience 3108
      Membrane Tranporter/Ion Channel MedChem Express HY-17468
      Membrane Tranporter/Ion Channel; MedChem Express HY-17468
      Membrane Transporter/Ion Channel TargetMol T0108
      Na+/2Cl-/K+ (NKCC) symporter inhibitor Tocris Bioscience 3108
      Na+/K+/Cl- Symporter Tocris Bioscience 3108
      NKCC MedChem Express HY-17468
      NKCC cotransportor TargetMol T0108
      Transporters Tocris Bioscience 3108
  • Gas Chromatography

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

Density: 1.3±0.1 g/cm3
Boiling Point: 571.2±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 90.1±3.0 kJ/mol
Flash Point: 299.3±32.9 °C
Index of Refraction: 1.612
Molar Refractivity: 94.1±0.4 cm3
#H bond acceptors: 7
#H bond donors: 4
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 2.78
ACD/LogD (pH 5.5): 1.44
ACD/BCF (pH 5.5): 3.09
ACD/KOC (pH 5.5): 28.09
ACD/LogD (pH 7.4): 0.03
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.10
Polar Surface Area: 127 Å2
Polarizability: 37.3±0.5 10-24cm3
Surface Tension: 60.0±3.0 dyne/cm
Molar Volume: 270.5±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) =  2.57

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  546.21  (Adapted Stein & Brown method)
    Melting Pt (deg C):  234.18  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.13E-011  (Modified Grain method)
    MP  (exp database):  230.5 deg C
    Subcooled liquid VP: 1.82E-009 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):  32.22
       log Kow used: 2.57 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  4.9143 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.37E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.682E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.57  (KowWin est)
  Log Kaw used:  -13.861  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.431
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8856
   Biowin2 (Non-Linear Model)     :   0.9858
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6090  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5724  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2487
   Biowin6 (MITI Non-Linear Model):   0.0354
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2327
 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):  2.43E-007 Pa (1.82E-009 mm Hg)
  Log Koa (Koawin est  ): 16.431
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  12.4 
       Octanol/air (Koa) model:  6.62E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.998 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  21.3416 E-12 cm3/molecule-sec
      Half-Life =     0.501 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     6.014 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.998 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  519.2
      Log Koc:  2.715 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 2.57 (estimated)

 Volatilization from Water:
    Henry LC:  3.37E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.317E+012  hours   (1.382E+011 days)
    Half-Life from Model Lake : 3.618E+013  hours   (1.508E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               3.31  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     3.21  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       1.87e-006       12           1000       
   Water     15.4            900          1000       
   Soil      84.5            1.8e+003     1000       
   Sediment  0.144           8.1e+003     0          
     Persistence Time: 1.67e+003 hr




                    

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