ChemSpider 2D Image | Furosemide | C12H11ClN2O5S

Furosemide

  • Molecular FormulaC12H11ClN2O5S
  • Average mass330.744 Da
  • Monoisotopic mass330.007721 Da
  • ChemSpider ID3322

More details:

Featured data source
The Merck Index Online

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

200-203-6 [EINECS]
4-Chlor-2-[(2-furylmethyl)amino]-5-sulfamoylbenzoesäure [German] [ACD/IUPAC Name]
4-Chlor-2-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzolcarbonsäure [German]
4-Chloro-2-[(2-furylmethyl)amino]-5-sulfamoylbenzoic acid [ACD/IUPAC Name]
4-Chloro-N-furfuryl-5-sulfamoylanthranilic acid
5-(Aminosulfonyl)-4-chloro-2-([2-furanylmethyl]amino)benzoic acid
54-31-9 [RN]
Acide 4-chloro-2-[(2-furylméthyl)amino]-5-sulfamoylbenzoïque [French] [ACD/IUPAC Name]
acide 4-chloro-2-[(furan-2-ylméthyl)amino]-5-sulfamoylbenzoïque [French]
Benzoic acid, 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

1584 [DBID]
7LXU5N7ZO5 [DBID]
MFCD00010549 [DBID]
AIDS001601 [DBID]
AIDS-001601 [DBID]
BRN 0840915 [DBID]
CCRIS 1951 [DBID]
CHEBI:47426 [DBID]
CHEBI:5198 [DBID]
D00331 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous

    • Safety:

      C03CA01 Wikidata Q388801

    • Target Organs:

      NKCC cotransporter inhibitor TargetMol T0837

    • Chemical Class:

      A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:47426, CHEBI:47426

    • Bio Activity:

      Furosemide (Lasix) is a loop diuretic inhibitor of Na+/2Cl-/K+ (NKCC) cotransporter of which used in the treatment of congestive heart failure and edema. MedChem Express
      Furosemide (Lasix) is a loop diuretic inhibitor of Na+/2Cl-/K+ (NKCC) cotransporter of which used in the treatment of congestive heart failure and edema.; Target: NKCC ; Furosemide (INN/BAN) or frusemide is a loop diuretic used in the treatment of congestive heart failure and edema. MedChem Express HY-B0135
      Furosemide (Lasix) is a loop diuretic inhibitor of Na+/2Cl-/K+ (NKCC) cotransporter of which used in the treatment of congestive heart failure and edema.;Target: NKCC Furosemide (INN/BAN) or frusemide is a loop diuretic used in the treatment of congestive heart failure and edema. It is most commonly marketed by Sanofi under the brand name Lasix, and also under the brand names Fusid and Frumex. It has also been used to prevent Thoroughbred and Standardbred race horses from bleeding through the nose during races.Along with some other diuretics, furosemide is also included on the World Anti-Doping Agency's banned drug list due to its alleged use as a masking agent for other drugs.Furosemide, like other loop diuretics, acts by inhibiting NKCC2, the luminal Na-K-2Cl symporter in the thick ascending limb of the loop of Henle. The action on the distal tubules is independent of any inhibitory effect on carbonic anhydrase or aldosterone; it also abolishes the corticomedullary osmotic grad MedChem Express HY-B0135
      Ion Pumps/Transporters Tocris Bioscience 3109
      Loop diuretic that inhibits the Na+/2Cl-/K+ (NKCC) symporter. Also acts as a non-competitive antagonist at GABAA receptors with ~ 100-fold greater selectivity for ?6-containing receptors than ?1-conta ining receptors. Tocris Bioscience 3109
      Loop diuretic that inhibits the Na+/2Cl-/K+ (NKCC) symporter. Also acts as a non-competitive antagonist at GABAA receptors with ~ 100-fold greater selectivity for ?6-containing receptors than ?1-containing receptors. Tocris Bioscience 3109
      Loop diuretic that inhibits the Na+/2Cl-/K+ (NKCC) symporter. Also acts as a non-competitive antagonist at GABAA receptors with ~ 100-fold greater selectivity for alpha6-containing receptors than alpha1-containing receptors. Tocris Bioscience 3109
      Membrane Tranporter/Ion Channel MedChem Express HY-B0135
      Membrane Tranporter/Ion Channel; MedChem Express HY-B0135
      Membrane Transporter/Ion Channel TargetMol T0837
      Na+/2Cl-/K+ (NKCC) symporter inhibitor. Also antagonizes GABAA Tocris Bioscience 3109
      Na+/K+/Cl- Symporter Tocris Bioscience 3109
      NKCC MedChem Express HY-B0135
      NKCC cotransportor TargetMol T0837
      Transporters Tocris Bioscience 3109
  • Gas Chromatography

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.6±0.1 g/cm3
Boiling Point: 582.1±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 91.5±3.0 kJ/mol
Flash Point: 305.9±32.9 °C
Index of Refraction: 1.658
Molar Refractivity: 75.8±0.4 cm3
#H bond acceptors: 7
#H bond donors: 4
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 3.10
ACD/LogD (pH 5.5): -0.06
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.76
ACD/LogD (pH 7.4): -0.78
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 131 Å2
Polarizability: 30.0±0.5 10-24cm3
Surface Tension: 75.3±3.0 dyne/cm
Molar Volume: 205.8±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) =  2.32
    Log Kow (Exper. database match) =  2.03
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  497.89  (Adapted Stein & Brown method)
    Melting Pt (deg C):  211.61  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.06E-011  (Modified Grain method)
    MP  (exp database):  295 deg C
    Subcooled liquid VP: 3.1E-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):  149.3
       log Kow used: 2.03 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  73.1 mg/L (30 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  93.53 mg/L
    Wat Sol (Exper. database match) =  73.10
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.94E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.919E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.03  (exp database)
  Log Kaw used:  -13.793  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.823
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3508
   Biowin2 (Non-Linear Model)     :   0.0396
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2146  (months      )
   Biowin4 (Primary Survey Model) :   3.1046  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0610
   Biowin6 (MITI Non-Linear Model):   0.0039
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0629
 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):  4.13E-006 Pa (3.1E-008 mm Hg)
  Log Koa (Koawin est  ): 15.823
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.726 
       Octanol/air (Koa) model:  1.63E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.963 
       Mackay model           :  0.983 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 112.2181 E-12 cm3/molecule-sec
      Half-Life =     0.095 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.144 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.973 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  188.3
      Log Koc:  2.275 

 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: 2.03 (expkow database)

 Volatilization from Water:
    Henry LC:  3.94E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.702E+012  hours   (1.126E+011 days)
    Half-Life from Model Lake : 2.948E+013  hours   (1.228E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               2.27  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.18  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       1.18e-006       2.29         1000       
   Water     22.5            1.44e+003    1000       
   Soil      77.4            2.88e+003    1000       
   Sediment  0.0922          1.3e+004     0          
     Persistence Time: 1.92e+003 hr

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