ChemSpider 2D Image | Dapsone | C12H12N2O2S

Dapsone

  • Molecular FormulaC12H12N2O2S
  • Average mass248.301 Da
  • Monoisotopic mass248.061951 Da
  • ChemSpider ID2849

More details:



Featured data source



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

1,1'-Sulfonylbis[4-aminobenzene]
201-248-4 [EINECS]
4,4'-Diaminodiphenylsulfone
4,4'-Sulfonylbisbenzeneamine
4,4'-Sulfonyldianilin [German] [ACD/IUPAC Name]
4,4'-Sulfonyldianiline [ACD/IUPAC Name]
4,4'-Sulfonyldianiline [French] [ACD/IUPAC Name]
4-Aminophenyl sulfone
4-Aminophenylsulfone
80-08-0 [RN]
More...

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

1676 [DBID]
8W5C518302 [DBID]
DRG 0036 [DBID]
HT 9664 [DBID]
MFCD00007887 [DBID]
1358F [DBID]
32960_FLUKA [DBID]
46158_RIEDEL [DBID]
A74807_ALDRICH [DBID]
AI3-08087 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      BEIGE POWDER NIH Clinical Collection [SMR000059064]
    • Toxicity:

      Organic Compound; Amine; Drug; Anti-Infective Agent; Anti-Inflammatory Agent; Antimalarial; Antimycobacterial; Folic Acid Antagonist; Leprostatic Agent; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D2482
    • Safety:

      22 Alfa Aesar A18976
      D10AX05 Wikidata Q422226
      GHS07 Biosynth Q-200436
      H302 Alfa Aesar A18976
      H302 Biosynth Q-200436
      IRRITANT Matrix Scientific 037407
      J04BA02 Wikidata Q422226
      P261 Alfa Aesar A18976
      P301+P312; P330 Biosynth Q-200436
      TBC SynQuest 8663-1-03
      Warning Alfa Aesar A18976
      Warning Biosynth Q-200436
      WARNING: Irritates skin and eyes, harmful if swallowed Alfa Aesar A18976
      Xn Abblis Chemicals AB1004833
    • Target Organs:

      Antibiotic TargetMol T0891
    • Chemical Class:

      A sulfone that is diphenylsulfone in which the hydrogen atom at the 4 position of each of the phenyl groups is substituted by an amino group. It is active against a wide range of bacteria, but is ma inly employed for its actions against <ital>Mycobacterium leprae</ital>, being used as part of multidrug regimens in the treatment of all forms of leprosy. ChEBI CHEBI:4325
      A sulfone that is diphenylsulfone in which the hydrogen atom at the 4 position of each of the phenyl groups is substituted by an amino group. It is active against a wide range of bacteria, but is ma inly employed for its actions against Mycobacterium leprae, being used as part of multidrug regimens in the treatment of all forms of leprosy. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4325
    • Compound Source:

      synthetic Microsource [01500222]
    • Bio Activity:

      Antibacterial MedChem Express HY-B0688
      Anti-infection MedChem Express HY-B0688
      Anti-infection; MedChem Express HY-B0688
      Dapsone is a sulfone active against a wide range of bacteria but mainly employed for its actions against mycobacterium leprae. MedChem Express
      Dapsone is a sulfone active against a wide range of bacteria but mainly employed for its actions against mycobacterium leprae.; Target: Antibacterial; Dapsone is an antibacterial most commonly used in combination with rifampicin and clofazimine as multidrug therapy (MDT) for the treatment of Mycobacterium leprae infections (leprosy). MedChem Express HY-B0688
      Dapsone is a sulfone active against a wide range of bacteria but mainly employed for its actions against mycobacterium leprae.;Target: AntibacterialDapsone is an antibacterial most commonly used in combination with rifampicin and clofazimine as multidrug therapy (MDT) for the treatment of Mycobacterium leprae infections (leprosy). Dapsone antagonized all of the I/R end points measured, showing a remarkable ability to decrease markers of damage through antioxidant, antiinflammatory, and anti-apoptotic effects [1]. As an antibacterial, dapsone inhibits bacterial synthesis of dihydrofolic acid, via competition with para-aminobenzoate for the active site of dihydropteroate synthetase. Dapsone has anti-inflammatory and immunomodulatory effects [2]. MedChem Express HY-B0688
      Microbiology & Virology TargetMol T0891
      Others TargetMol T0891
  • Gas Chromatography

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

Density: 1.4±0.1 g/cm3
Boiling Point: 511.7±35.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 78.3±3.0 kJ/mol
Flash Point: 263.2±25.9 °C
Index of Refraction: 1.662
Molar Refractivity: 67.5±0.4 cm3
#H bond acceptors: 4
#H bond donors: 4
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 0.94
ACD/LogD (pH 5.5): 1.08
ACD/BCF (pH 5.5): 3.87
ACD/KOC (pH 5.5): 91.67
ACD/LogD (pH 7.4): 1.08
ACD/BCF (pH 7.4): 3.87
ACD/KOC (pH 7.4): 91.67
Polar Surface Area: 95 Å2
Polarizability: 26.8±0.5 10-24cm3
Surface Tension: 62.6±3.0 dyne/cm
Molar Volume: 182.4±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) =  0.77
    Log Kow (Exper. database match) =  0.97
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  438.00  (Adapted Stein & Brown method)
    Melting Pt (deg C):  182.92  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.68E-008  (Modified Grain method)
    MP  (exp database):  175.5 deg C
    Subcooled liquid VP: 9.74E-007 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):  3589
       log Kow used: 0.97 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  380 mg/L (37 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  237.53 mg/L
    Wat Sol (Exper. database match) =  380.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aromatic Amines

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.11E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.440E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.97  (exp database)
  Log Kaw used:  -11.896  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.866
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1618
   Biowin2 (Non-Linear Model)     :   0.0130
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3806  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.2727  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2762
   Biowin6 (MITI Non-Linear Model):   0.0022
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4830
 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):  0.00013 Pa (9.74E-007 mm Hg)
  Log Koa (Koawin est  ): 12.866
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0231 
       Octanol/air (Koa) model:  1.8 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.455 
       Mackay model           :  0.649 
       Octanol/air (Koa) model:  0.993 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  46.0288 E-12 cm3/molecule-sec
      Half-Life =     0.232 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.789 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.552 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1272
      Log Koc:  3.105 

 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: 0.97 (expkow database)

 Volatilization from Water:
    Henry LC:  3.11E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.966E+010  hours   (1.236E+009 days)
    Half-Life from Model Lake : 3.236E+011  hours   (1.348E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               1.88  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.79  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       7.76e-007       5.58         1000       
   Water     41              900          1000       
   Soil      58.9            1.8e+003     1000       
   Sediment  0.0859          8.1e+003     0          
     Persistence Time: 1.05e+003 hr




                    

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