Ciclopirox C12H17NO2 structure

Flashcard maker : Lily Taylor

Molecular Formula C12H17NO2
Average mass 207.269 Da
Density 1.2±0.1 g/cm3
Boiling Point 350.0±25.0 °C at 760 mmHg
Flash Point 165.5±23.2 °C
Molar Refractivity 58.0±0.3 cm3
Polarizability 23.0±0.5 10-24cm3
Surface Tension 51.8±3.0 dyne/cm
Molar Volume 173.7±3.0 cm3
  • Experimental data
  • Predicted – ACD/Labs
  • Predicted – EPISuite
  • Predicted – ChemAxon
  • Experimental Physico-chemical Properties
    • Experimental Melting Point:

      144 °C Jean-Claude Bradley Open Melting Point Dataset 16819, 22063
    • Experimental Solubility:

      10 mM in DMSO MedChem Express HY-B0450
      DMSO 42 mg/mL; Water <1 mg/mL MedChem Express HY-B0450
  • Miscellaneous
    • Target Organs:

      ATPase inhibitor TargetMol T1482
    • Therapeutical Effect:

      Antifungal Agents Sean Ekins
    • Drug Status:

      approved BIONET-Key Organics KS-5085
    • Bio Activity:

      Antifungal MedChem Express HY-B0450
      Anti-infection MedChem Express HY-B0450
      Anti-infection; MedChem Express HY-B0450
      Ciclopirox (Penlac) is a synthetic antifungal agent. MedChem Express
      Ciclopirox (Penlac) is a synthetic antifungal agent.; Target: Antifungal; Ciclopirox is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. MedChem Express HY-B0450
      Ciclopirox (Penlac) is a synthetic antifungal agent.;Target: AntifungalCiclopirox is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. It is most useful against Tinea versicolor. The mechanism of action of ciclopirox is poorly understood [1]. However, loss of function of certain catalase and peroxidase enzymes has been implicated as the mechanism of action, as well as various other components of cellular metabolism. In a study conducted to further elucidate ciclopirox’s mechanism, several Saccharomyces cerevisiae mutants were screened and tested. Results from interpretation of the effects of both the drug treatment and mutation suggested that ciclopirox may exert its effect by disrupting DNA repair, cell division signals and structures (mitotic spindles) as well as some elements of intracellular transport [2]. It acts by inhibiting the membrane transfer system by interrupting the Na+ K+ ATPase [1]. It is currently being investigated as an alter MedChem Express HY-B0450
      Membrane Transporter/Ion Channel TargetMol T1482
      Na+, K+-ATPase TargetMol T1482
  • Gas Chromatography
    • Retention Index (Kovats):

      1784 (estimated with error: 89) NIST Spectra mainlib_248393

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

Density: 1.2±0.1 g/cm3
Boiling Point: 350.0±25.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 68.9±6.0 kJ/mol
Flash Point: 165.5±23.2 °C
Index of Refraction: 1.582
Molar Refractivity: 58.0±0.3 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 2.59
ACD/LogD (pH 5.5): 1.79
ACD/BCF (pH 5.5): 13.09
ACD/KOC (pH 5.5): 209.28
ACD/LogD (pH 7.4): 0.69
ACD/BCF (pH 7.4): 1.02
ACD/KOC (pH 7.4): 16.25
Polar Surface Area: 41 Å2
Polarizability: 23.0±0.5 10-24cm3
Surface Tension: 51.8±3.0 dyne/cm
Molar Volume: 173.7±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) = 2.73

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
 Boiling Pt (deg C): 379.86 (Adapted Stein & Brown method)
 Melting Pt (deg C): 135.51 (Mean or Weighted MP)
 VP(mm Hg,25 deg C): 4.47E-008 (Modified Grain method)
 MP (exp database): 144 deg C
 Subcooled liquid VP: 7.17E-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): 187.5
 log Kow used: 2.73 (estimated)
 no-melting pt equation used

 Water Sol Estimate from Fragments:
 Wat Sol (v1.01 est) = 4680.3 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
 Bond Method : 1.02E-010 atm-m3/mole
 Group Method: Incomplete
 Henrys LC [VP/WSol estimate using EPI values]: 6.502E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
 Log Kow used: 2.73 (KowWin est)
 Log Kaw used: -8.380 (HenryWin est)
 Log Koa (KOAWIN v1.10 estimate): 11.110
 Log Koa (experimental database): None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
 Biowin1 (Linear Model) : 0.6489
 Biowin2 (Non-Linear Model) : 0.5163
 Expert Survey Biodegradation Results:
 Biowin3 (Ultimate Survey Model): 2.7411 (weeks-months)
 Biowin4 (Primary Survey Model) : 3.5487 (days-weeks )
 MITI Biodegradation Probability:
 Biowin5 (MITI Linear Model) : 0.2194
 Biowin6 (MITI Non-Linear Model): 0.0888
 Anaerobic Biodegradation Probability:
 Biowin7 (Anaerobic Linear Model): 0.0488
 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): 9.56E-005 Pa (7.17E-007 mm Hg)
 Log Koa (Koawin est ): 11.110
 Kp (particle/gas partition coef. (m3/ug)):
 Mackay model : 0.0314 
 Octanol/air (Koa) model: 0.0316 
 Fraction sorbed to airborne particulates (phi):
 Junge-Pankow model : 0.531 
 Mackay model : 0.715 
 Octanol/air (Koa) model: 0.717 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
 Hydroxyl Radicals Reaction:
 OVERALL OH Rate Constant = 79.7363 E-12 cm3/molecule-sec
 Half-Life = 0.134 Days (12-hr day; 1.5E6 OH/cm3)
 Half-Life = 1.610 Hrs
 Ozone Reaction:
 OVERALL Ozone Rate Constant = 34.222500 E-17 cm3/molecule-sec
 Half-Life = 0.033 Days (at 7E11 mol/cm3)
 Half-Life = 48.221 Min
 Fraction sorbed to airborne particulates (phi): 0.623 (Junge,Mackay)
 Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
 Koc : 3211
 Log Koc: 3.507 

 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 = 1.401 (BCF = 25.2)
 log Kow used: 2.73 (estimated)

 Volatilization from Water:
 Henry LC: 1.02E-010 atm-m3/mole (estimated by Bond SAR Method)
 Half-Life from Model River: 8.264E+006 hours (3.443E+005 days)
 Half-Life from Model Lake : 9.015E+007 hours (3.756E+006 days)

 Removal In Wastewater Treatment:
 Total removal: 3.95 percent
 Total biodegradation: 0.11 percent
 Total sludge adsorption: 3.84 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 0.00198 0.643 1000 
 Water 14.6 900 1000 
 Soil 85.2 1.8e+003 1000 
 Sediment 0.187 8.1e+003 0 
 Persistence Time: 1.64e+003 hr




 

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