ChemSpider 2D Image | Pafuramidine | C20H20N4O3

Pafuramidine

  • Molecular FormulaC20H20N4O3
  • Average mass364.398 Da
  • Monoisotopic mass364.153534 Da
  • ChemSpider ID4586633

More details:






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

186953-56-0 [RN]
4,4'-(2,5-Furandiyl)bis(N'-methoxybenzenecarboximidamide) [ACD/IUPAC Name]
4,4'-(2,5-Furandiyl)bis(N'-methoxybenzolcarboximidamid) [German] [ACD/IUPAC Name]
4,4'-(2,5-Furanediyl)bis(N'-méthoxybenzènecarboximidamide) [French] [ACD/IUPAC Name]
4,4'-furan-2,5-diylbis(N-methoxybenzenecarboximidamide)
8760
Benzenecarboximidamide, 4,4'-(2,5-furandiyl)bis[N'-methoxy- [ACD/Index Name]
H1VG379J2X
Pafuramidine [Wiki]
[2,5-bis[4-(methoxyamidino)phenyl]furan]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS022387 [DBID]
AIDS-022387 [DBID]
DB289 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Bio Activity:

      Anti-infection MedChem Express HY-14932
      Anti-infection; MedChem Express HY-14932
      Antiparasitic MedChem Express HY-14932
      Pafuramidine (DB289) is an orally bioavailable prodrug of furamidine, which has clinical activity against Pneumocystis pneumonia. MedChem Express
      Pafuramidine (DB289) is an orally bioavailable prodrug of furamidine, which has clinical activity against Pneumocystis pneumonia.; IC50 Value: 4.5 nM (In vitro inhibitory activity against Trypanosoma brucei rhodesiense) [4]; Target: Antiparasitic; DB289 (pafuramidine maleate; 2,5-bis[4-(N-methoxyamidino)phenyl]furan monomaleate) is a prodrug of DB75 (furamidine dihydrochloride; 2,5-bis(4-guanylphenyl)furan dihydrochloride), an aromatic dication related to pentamidine that has demonstrated good efficacy against African trypanosomiasis, Pneumocystis carinii pneumonia, and malaria, but lacks adequate oral availability. MedChem Express HY-14932
      Pafuramidine (DB289) is an orally bioavailable prodrug of furamidine, which has clinical activity against Pneumocystis pneumonia.;IC50 Value: 4.5 nM (In vitro inhibitory activity against Trypanosoma brucei rhodesiense) [4];Target: AntiparasiticDB289 (pafuramidine maleate; 2,5-bis[4-(N-methoxyamidino)phenyl]furan monomaleate) is a prodrug of DB75 (furamidine dihydrochloride; 2,5-bis(4-guanylphenyl)furan dihydrochloride), an aromatic dication related to pentamidine that has demonstrated good efficacy against African trypanosomiasis, Pneumocystis carinii pneumonia, and malaria, but lacks adequate oral availability. ;In vitro: The results of this investigation suggest that DB75 inhibits mitochondrial function. Yeast cells relying upon mitochondrial metabolism for energy production are especially sensitive to DB75 [1].;In vivo: Clearance of DB289 approximated the liver plasma flow and its large volume of distribution was consistent with extensive tissue binding. Plasma protein bindi MedChem Express HY-14932

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

Density: 1.3±0.1 g/cm3
Boiling Point: 524.5±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 79.8±3.0 kJ/mol
Flash Point: 271.0±32.9 °C
Index of Refraction: 1.613
Molar Refractivity: 100.8±0.5 cm3
#H bond acceptors: 7
#H bond donors: 4
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 4.05
ACD/LogD (pH 5.5): 3.07
ACD/BCF (pH 5.5): 123.70
ACD/KOC (pH 5.5): 1067.67
ACD/LogD (pH 7.4): 3.11
ACD/BCF (pH 7.4): 134.96
ACD/KOC (pH 7.4): 1164.84
Polar Surface Area: 108 Å2
Polarizability: 40.0±0.5 10-24cm3
Surface Tension: 47.0±7.0 dyne/cm
Molar Volume: 289.6±7.0 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) =  3.87

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  522.12  (Adapted Stein & Brown method)
    Melting Pt (deg C):  222.93  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.74E-011  (Modified Grain method)
    Subcooled liquid VP: 7.53E-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):  2.517
       log Kow used: 3.87 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3.2959 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.51E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.093E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.87  (KowWin est)
  Log Kaw used:  -14.209  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.079
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5741
   Biowin2 (Non-Linear Model)     :   0.1029
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3939  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3220  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2890
   Biowin6 (MITI Non-Linear Model):   0.0012
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2774
 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):  1E-006 Pa (7.53E-009 mm Hg)
  Log Koa (Koawin est  ): 18.079
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.99 
       Octanol/air (Koa) model:  2.94E+005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.991 
       Mackay model           :  0.996 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 100.4401 E-12 cm3/molecule-sec
      Half-Life =     0.106 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.278 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.993 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2.238E+007
      Log Koc:  7.350 

 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 = 2.279 (BCF = 190.1)
       log Kow used: 3.87 (estimated)

 Volatilization from Water:
    Henry LC:  1.51E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.402E+012  hours   (3.084E+011 days)
    Half-Life from Model Lake : 8.075E+013  hours   (3.364E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              24.50  percent
    Total biodegradation:        0.28  percent
    Total sludge adsorption:    24.23  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       1.91e-007       2.56         1000       
   Water     11.1            900          1000       
   Soil      87              1.8e+003     1000       
   Sediment  1.93            8.1e+003     0          
     Persistence Time: 1.87e+003 hr




                    

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