ChemSpider 2D Image | Bifonazole | C22H18N2

Bifonazole

  • Molecular FormulaC22H18N2
  • Average mass310.392 Da
  • Monoisotopic mass310.147003 Da
  • ChemSpider ID2287

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(±)-1-(p,a-Diphenylbenzyl)imidazole
(±)-Bifonazole
1-([1,1'-Biphenyl]-4-ylphenylmethyl)-1H-imidazole
1-[4-Biphenylyl(phenyl)methyl]-1H-imidazol [German] [ACD/IUPAC Name]
1-[4-Biphenylyl(phenyl)methyl]-1H-imidazole [ACD/IUPAC Name]
1-[4-Biphénylyl(phényl)méthyl]-1H-imidazole [French] [ACD/IUPAC Name]
1-[Biphenyl-4-yl(phenyl)methyl]-1H-imidazol
1-[biphenyl-4-yl(phenyl)methyl]-1H-imidazole
1-[biphenyl-4-yl(phenyl)methyl]imidazole
1-[PHENYL-(4-PHENYLPHENYL)-METHYL]IMIDAZOLE
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS009214 [DBID]
AIDS-009214 [DBID]
B8773_SIGMA [DBID]
BRN 0618427 [DBID]
D01775 [DBID]
KBio3_002922 [DBID]
MLS000028576 [DBID]
SMR000058970 [DBID]
SPBio_000129 [DBID]
Spectrum2_000035 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      D01AC10 Wikidata Q421162
      GHS07 Biosynth Q-200718
      H302 Biosynth Q-200718
      P261; P280; P302+P352; P304+P340; P305+P351+P338; P312 Biosynth Q-200718
      Warning Biosynth Q-200718
    • Target Organs:

      Antifungal; Demethylase inhibitor TargetMol T1187
    • Chemical Class:

      A member of the class of imidazoles carrying an <locant>alpha</locant>-(biphenyl-4-yl)benzyl substituent at position 1. ChEBI CHEBI:78692
    • Drug Status:

      approved BIONET-Key Organics KS-5111
    • Compound Source:

      synthetic Microsource [01505309]
    • Bio Activity:

      Antifungal MedChem Express HY-B0301
      Anti-infection MedChem Express HY-B0301
      Anti-infection; MedChem Express HY-B0301
      Bifonazole is an imidazole antifungal drug. MedChem Express
      Bifonazole is an imidazole antifungal drug.; Target: Antifungal; Bifonazole, a new broad-spectrum antimycotic, interferes with sterol biosynthesis. MedChem Express HY-B0301
      Bifonazole is an imidazole antifungal drug.;Target: AntifungalBifonazole, a new broad-spectrum antimycotic, interferes with sterol biosynthesis. In dermatophytes bifonazole additionally inhibits directly HMG-CoA-reductase. bifonazole possesses a sequential mode of action, namely inhibition of cytochrome P450-dependent C14-demethylation of sterols and direct inhibition of HMG-CoA-reductase. In vitro bifonazole shows a strongly pH-dependent efficacy. The uptake kinetics of bifonazole have been measured with different pathogens [1]. Bifonazole additionally leads to a generally decreased rate of sterol biosynthesis as compared to clotrimazole, due to a direct inhibition of microsomal HMG-CoA-reductase. The additional fungicidal effects of bifonazole are considered to originate from a sequential action by inhibition of HMG-CoA-reductase and of cytochrome P450 [2]. bifonazole were affected by choice of medium with Kimmig's agar generally giving the lowest MIC's. Bifonazole MICs were show MedChem Express HY-B0301
      Microbiology & Virology TargetMol T1187
      others;CYP51 TargetMol T1187
      Topical antimycotic Zerenex Molecular [ZBioX-0008]
  • Gas Chromatography

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

Density: 1.1±0.1 g/cm3
Boiling Point: 491.7±24.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 73.0±3.0 kJ/mol
Flash Point: 251.2±22.9 °C
Index of Refraction: 1.616
Molar Refractivity: 100.8±0.5 cm3
#H bond acceptors: 2
#H bond donors: 0
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 4.84
ACD/LogD (pH 5.5): 4.16
ACD/BCF (pH 5.5): 473.05
ACD/KOC (pH 5.5): 1417.85
ACD/LogD (pH 7.4): 5.18
ACD/BCF (pH 7.4): 4894.37
ACD/KOC (pH 7.4): 14669.72
Polar Surface Area: 18 Å2
Polarizability: 39.9±0.5 10-24cm3
Surface Tension: 43.1±7.0 dyne/cm
Molar Volume: 288.1±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) =  5.71
    Log Kow (Exper. database match) =  4.77
       Exper. Ref:  BioByte (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  494.51  (Adapted Stein & Brown method)
    Melting Pt (deg C):  197.08  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.83E-010  (Modified Grain method)
    Subcooled liquid VP: 3.78E-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):  0.9008
       log Kow used: 4.77 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.024895 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.01E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.643E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.77  (exp database)
  Log Kaw used:  -5.785  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.555
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8560
   Biowin2 (Non-Linear Model)     :   0.9002
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5572  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4097  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0814
   Biowin6 (MITI Non-Linear Model):   0.0158
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3168
 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):  5.04E-006 Pa (3.78E-008 mm Hg)
  Log Koa (Koawin est  ): 10.555
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.595 
       Octanol/air (Koa) model:  0.00881 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.956 
       Mackay model           :  0.979 
       Octanol/air (Koa) model:  0.413 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  50.0295 E-12 cm3/molecule-sec
      Half-Life =     0.214 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.566 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.967 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  9.868E+005
      Log Koc:  5.994 

 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 = 2.973 (BCF = 939.5)
       log Kow used: 4.77 (expkow database)

 Volatilization from Water:
    Henry LC:  4.01E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.573E+004  hours   (1072 days)
    Half-Life from Model Lake : 2.808E+005  hours   (1.17E+004 days)

 Removal In Wastewater Treatment:
    Total removal:              69.10  percent
    Total biodegradation:        0.62  percent
    Total sludge adsorption:    68.48  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       0.133           5.13         1000       
   Water     12.4            900          1000       
   Soil      70.3            1.8e+003     1000       
   Sediment  17.2            8.1e+003     0          
     Persistence Time: 1.43e+003 hr




                    

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