ChemSpider 2D Image | Sulfamethizole | C9H10N4O2S2

Sulfamethizole

  • Molecular FormulaC9H10N4O2S2
  • Average mass270.331 Da
  • Monoisotopic mass270.024506 Da
  • ChemSpider ID5137

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Featured data source



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

144-82-1 [RN]
205-641-1 [EINECS]
25W8454H16
4-Amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide [ACD/IUPAC Name]
4-Amino-N-(5-méthyl-1,3,4-thiadiazol-2-yl)benzènesulfonamide [French] [ACD/IUPAC Name]
4-Amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzolsulfonamid [German] [ACD/IUPAC Name]
529
Benzenesulfonamide, 4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)- [ACD/Index Name]
Sulfamethizole [INN] [JAN] [USAN] [Wiki]
sulfamethizolum [Latin]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

46842_RIEDEL [DBID]
AI3-50149 [DBID]
AIDS027751 [DBID]
AIDS-027751 [DBID]
C08050 [DBID]
CCRIS 756 [DBID]
D00870 [DBID]
DivK1c_000141 [DBID]
HSDB 4379 [DBID]
KBio1_000141 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      B05CA04 Wikidata Q3976824
      D06BA04 Wikidata Q3976824
      J01EB02 Wikidata Q3976824
      S01AB01 Wikidata Q3976824
    • Target Organs:

      Antibiotic;DHPS inhibitor TargetMol T0754
    • Chemical Class:

      A sulfonamide consisting of a 1,3,4-thiadiazole nucleus with a methyl substituent at C-5 and a 4-aminobenzenesulfonamido group at C-2. ChEBI CHEBI:9331
    • Compound Source:

      synthetic Microsource [01500549]
    • Bio Activity:

      Antibacterial MedChem Express HY-B0333
      Anti-infection MedChem Express HY-B0333
      Anti-infection; MedChem Express HY-B0333
      DHPS TargetMol T0754
      Microbiology & Virology TargetMol T0754
      Sulfamethizole is a sulfathiazole antibacterial agent. MedChem Express
      Sulfamethizole is a sulfathiazole antibacterial agent.; Target: Antibacterial; Sulfamethizole is a sulfathiazole antibacterial agent. MedChem Express HY-B0333
      Sulfamethizole is a sulfathiazole antibacterial agent.;Target: AntibacterialSulfamethizole is a sulfathiazole antibacterial agent. Sulfamethizole is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid. Sulfamethizole, an inhibitor of dihydropteroate synthetase and the formation of folic acid, inhibited bioluminescence more than growth [1]. Treatment with sulfamethizole resulted in a significant reduction in bacterial counts in all samples from a susceptible strain (MIC, 128 micro g/ml) and a resistant strain (MIC, 512 micro g/ml). Infection with a sulII gene-positive strain (MIC, >2,048 micro g/ml) could not be treated with sulfamethizole, as no effect could be demonstrated in the urine, bladder, or kidneys [2]. MedChem Express HY-B0333

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

Density: 1.6±0.1 g/cm3
Boiling Point: 504.9±52.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 77.4±3.0 kJ/mol
Flash Point: 259.1±30.7 °C
Index of Refraction: 1.687
Molar Refractivity: 65.9±0.4 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 0.51
ACD/LogD (pH 5.5): 0.21
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 22.08
ACD/LogD (pH 7.4): -1.14
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 135 Å2
Polarizability: 26.1±0.5 10-24cm3
Surface Tension: 86.4±3.0 dyne/cm
Molar Volume: 173.0±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) =  0.41
    Log Kow (Exper. database match) =  0.54
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  471.67  (Adapted Stein & Brown method)
    Melting Pt (deg C):  199.36  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.63E-009  (Modified Grain method)
    MP  (exp database):  208 deg C
    Subcooled liquid VP: 1.42E-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):  6292
       log Kow used: 0.54 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1050 mg/L (37 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1544.7 mg/L
    Wat Sol (Exper. database match) =  1050.00
       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 :   2.63E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.215E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.54  (exp database)
  Log Kaw used:  -11.969  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.509
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4398
   Biowin2 (Non-Linear Model)     :   0.1034
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3920  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.2808  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1754
   Biowin6 (MITI Non-Linear Model):   0.0033
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1952
 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):  1.89E-005 Pa (1.42E-007 mm Hg)
  Log Koa (Koawin est  ): 12.509
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.158 
       Octanol/air (Koa) model:  0.793 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.851 
       Mackay model           :  0.927 
       Octanol/air (Koa) model:  0.984 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  23.8504 E-12 cm3/molecule-sec
      Half-Life =     0.448 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     5.382 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.889 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  165.9
      Log Koc:  2.220 

 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: 0.54 (expkow database)

 Volatilization from Water:
    Henry LC:  2.63E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  3.66E+010  hours   (1.525E+009 days)
    Half-Life from Model Lake : 3.993E+011  hours   (1.664E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       4.08e-006       10.8         1000       
   Water     44.2            900          1000       
   Soil      55.7            1.8e+003     1000       
   Sediment  0.0878          8.1e+003     0          
     Persistence Time: 1e+003 hr




                    

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