ChemSpider 2D Image | Luliconazole | C14H9Cl2N3S2

Luliconazole

  • Molecular FormulaC14H9Cl2N3S2
  • Average mass354.277 Da
  • Monoisotopic mass352.961487 Da
  • ChemSpider ID2273807
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 1 of 1 defined stereocentres


More details:



Featured data source



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

(-)-(E)-((4R)-4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene)(1H-imidazol-1-yl)acetonitrile
(2E)-[(4R)-4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene](1H-imidazol-1-yl)acetonitrile [ACD/IUPAC Name]
(2E)-[(4R)-4-(2,4-Dichlorophényl)-1,3-dithiolan-2-ylidène](1H-imidazol-1-yl)acétonitrile [French] [ACD/IUPAC Name]
(2E)-[(4R)-4-(2,4-Dichlorphenyl)-1,3-dithiolan-2-yliden](1H-imidazol-1-yl)acetonitril [German] [ACD/IUPAC Name]
187164-19-8 [RN]
1H-Imidazole-1-acetonitrile, α-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-, (αE)- [ACD/Index Name]
Lulicon [Trade name]
Luzu [Trade name]
(2E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene](1H-imidazol-1-yl)ethanenitrile
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

NND-502 [DBID]
PR-2699 [DBID]
AIDS106695 [DBID]
AIDS-106695 [DBID]
C13478 [DBID]
D01980 [DBID]
RE91AN4S8G [DBID]
UNII:RE91AN4S8G [DBID]
UNII-RE91AN4S8G [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Target Organs:

      Antifungal TargetMol T2411
    • Bio Activity:

      Antifungal MedChem Express HY-14283
      antifungal TargetMol T2411
      Anti-infection; MedChem Express HY-14283
      Luliconazole(NND 502) is an azole antifungal indicated for the topical treatment of interdigital tinea pedis.;IC50 Value: ;Target: AntifungalLuliconazole is an antifungal that belongs to the azole class. Although the exact mechanism of action against dermatophytes is unknown, luliconazole appears to inhibit ergosterol synthesis by inhibiting the enzyme lanosterol demethylase. Inhibition of this enzyme?s activity by azoles results in decreased amounts of ergosterol, a constituent of fungal cell membranes, and a corresponding accumulation of lanosterol. ;In a fertility study in rats, subcutaneous doses of 1, 5 and 25 mg/kg/day luliconazole were administered prior to and during mating and through early pregnancy. Treatment related effects on reproductive function were noted in females (decreased live embryos and decreased corpus luteum) at 5 and 25 mg/kg/day and males (decreased sperm counts) at 25 mg/kg/day. No treatment related effects on fertility or reproductive function were no MedChem Express HY-14283
      Microbiology & Virology TargetMol T2411

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

Density: 1.5±0.1 g/cm3
Boiling Point: 499.1±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 76.7±3.0 kJ/mol
Flash Point: 255.6±31.5 °C
Index of Refraction: 1.734
Molar Refractivity: 93.2±0.5 cm3
#H bond acceptors: 3
#H bond donors: 0
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 3.98
ACD/LogD (pH 5.5): 4.51
ACD/BCF (pH 5.5): 1559.29
ACD/KOC (pH 5.5): 6681.58
ACD/LogD (pH 7.4): 4.51
ACD/BCF (pH 7.4): 1587.16
ACD/KOC (pH 7.4): 6801.03
Polar Surface Area: 92 Å2
Polarizability: 36.9±0.5 10-24cm3
Surface Tension: 60.5±7.0 dyne/cm
Molar Volume: 232.4±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) =  3.61

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  515.95  (Adapted Stein & Brown method)
    Melting Pt (deg C):  220.05  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.91E-011  (Modified Grain method)
    Subcooled liquid VP: 1.08E-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):  2.622
       log Kow used: 3.61 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  31.6 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Allylic/Vinyl Nitriles
       Imidazoles

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.64E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.584E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.61  (KowWin est)
  Log Kaw used:  -9.967  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.577
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5210
   Biowin2 (Non-Linear Model)     :   0.1964
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9207  (months      )
   Biowin4 (Primary Survey Model) :   2.9407  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1985
   Biowin6 (MITI Non-Linear Model):   0.0012
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.6280
 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):  1.44E-006 Pa (1.08E-008 mm Hg)
  Log Koa (Koawin est  ): 13.577
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.08 
       Octanol/air (Koa) model:  9.27 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.987 
       Mackay model           :  0.994 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  75.8080 E-12 cm3/molecule-sec
      Half-Life =     0.141 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.693 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.105000 E-17 cm3/molecule-sec
      Half-Life =    10.914 Days (at 7E11 mol/cm3)
   Fraction sorbed to airborne particulates (phi): 0.99 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2.25E+004
      Log Koc:  4.352 

 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 = 2.079 (BCF = 120)
       log Kow used: 3.61 (estimated)

 Volatilization from Water:
    Henry LC:  2.64E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.174E+008  hours   (1.739E+007 days)
    Half-Life from Model Lake : 4.554E+009  hours   (1.897E+008 days)

 Removal In Wastewater Treatment:
    Total removal:              15.79  percent
    Total biodegradation:        0.21  percent
    Total sludge adsorption:    15.58  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       0.00149         3.34         1000       
   Water     9.1             1.44e+003    1000       
   Soil      89.9            2.88e+003    1000       
   Sediment  1.03            1.3e+004     0          
     Persistence Time: 2.82e+003 hr




                    

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