ChemSpider 2D Image | Ciclopirox | C12H17NO2

Ciclopirox

  • Molecular FormulaC12H17NO2
  • Average mass207.269 Da
  • Monoisotopic mass207.125931 Da
  • ChemSpider ID2647

More details:



Featured data source



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

(6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone)
19W019ZDRJ
2(1H)-Pyridinone, 6-cyclohexyl-1-hydroxy-4-methyl- [ACD/Index Name]
249-577-2 [EINECS]
29342-05-0 [RN]
3101
6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinon [German] [ACD/IUPAC Name]
6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone [ACD/IUPAC Name]
6-Cyclohexyl-1-hydroxy-4-méthyl-2(1H)-pyridinone [French] [ACD/IUPAC Name]
6-Cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-on
More...

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

AIDS093044 [DBID]
AIDS-093044 [DBID]
D03488 [DBID]
KBio3_001261 [DBID]
KBioGR_000816 [DBID]
LS-174247 [DBID]
Prestwick0_000541 [DBID]
Prestwick1_000541 [DBID]
SPBio_000252 [DBID]
SPBio_002502 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      D01AE14 Wikidata Q419468
      G01AX12 Wikidata Q419468
    • Target Organs:

      ATPase inhibitor TargetMol T1482
    • Chemical Class:

      A cyclic hydroxamic acid that is 1-hydroxypyridin-2(1<element>H</element>)-one in which the hydrogens at positions 4 and 6 are substituted by methyl and cyclohexyl groups, repectively. A broad spectru m antigfungal agent, it also exhibits antibacterial activity against many Gram-positive and Gram-negative bacteria, and has anti-inflammatory properties. It is used a a topical treatment of fungal ski n and nail infections. ChEBI CHEBI:453011
    • 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
      Demethylases Tocris Bioscience 6384
      Enzymes Tocris Bioscience 6384
      Histone Demethylases Tocris Bioscience 6384
      Membrane Transporter/Ion Channel TargetMol T1482
      Na+, K+-ATPase TargetMol T1482
      Pan-histone demethylase inhibitor Tocris Bioscience 6384
      Pan-histone demethylase inhibitor. Exhibits no significant effect on histone deacetylases. Inhibits MYC-signaling and proliferation of neuroblastoma cells. Promotes Cdc25A-degradation in cancer cells. Antifungal. Tocris Bioscience 6384
  • Gas Chromatography

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




                    

Click to predict properties on the Chemicalize site





Feedback Form