ChemSpider 2D Image | Terbinafine | C21H25N

Terbinafine

  • Molecular FormulaC21H25N
  • Average mass291.430 Da
  • Monoisotopic mass291.198700 Da
  • ChemSpider ID1266005
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

(2E)-N,6,6-Trimethyl-N-(1-naphthylmethyl)-2-hepten-4-in-1-amin [German] [ACD/IUPAC Name]
(2E)-N,6,6-Trimethyl-N-(1-naphthylmethyl)-2-hepten-4-yn-1-amine [ACD/IUPAC Name]
(2E)-N,6,6-Trimethyl-N-(1-naphthylmethyl)hept-2-en-4-yn-1-amine
(2E)-N,6,6-Triméthyl-N-(1-naphtylméthyl)-2-heptén-4-yn-1-amine [French] [ACD/IUPAC Name]
1-Naphthalenemethanamine, N-[(2E)-6,6-dimethyl-2-hepten-4-yn-1-yl]-N-methyl- [ACD/Index Name]
1-naphthalenemethanamine, N-[(2E)-6,6-dimethyl-2-hepten-4-ynyl]-N-methyl-
91161-71-6 [RN]
Lamisil [Trade name]
N,6,6-trimethyl-N-(1-naphthalenylmethyl)-1-hept-2-en-4-ynamine
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS017397 [DBID]
AIDS-017397 [DBID]
BRN 4256376 [DBID]
C08079 [DBID]
D02375 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      D01AE15 Wikidata Q415259
      D01BA02 Wikidata Q415259
    • Chemical Class:

      A tertiary amine that is <element>N</element>-methyl-1-naphthalenemethylamine in which the amino hydrogen is replaced by a 3-(<ital>tert</ital>butylethynyl)allyl group. An antifungal agent administere d orally (generally as the hydrochloride salt) for the treatment of skin and nail infections. ChEBI CHEBI:9448
    • Bio Activity:

      Antifungal MedChem Express HY-17395A
      Anti-infection; MedChem Express HY-17395A
      Terbinafine is an allylamine antifungal agent which has fungicidal activity against a wide variety of dermatophytes, moulds and certain dimorphic fungi, and fungistatic activity against Candida albica ns. MedChem Express
      Terbinafine is an allylamine antifungal agent which has fungicidal activity against a wide variety of dermatophytes, moulds and certain dimorphic fungi, and fungistatic activity against Candida albicans.;Target: Antifungal;Terbinafine is an allylamine antifungal agent which has fungicidal activity against a wide variety of dermatophytes, moulds and certain dimorphic fungi, and fungistatic activity against Candida albicans. It is highly lipophilic in nature and tends to accumulate in skin, nails, and fatty tissues. Like other allylamines, terbinafine inhibits ergosterol synthesis by inhibiting squalene epoxidase, an enzyme that is part of the fungal cell membranesynthesis pathway. Because terbinafine prevents conversion of squalene to lanosterol, ergosterol cannot be synthesized. This is thought to change cell membrane permeability, causing fungal cell lysis.;Terbinafine hydrochloride is a white fine crystalline powder that is freely soluble in methanol and dichloromethane, soluble MedChem Express HY-17395A
  • Gas Chromatography

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

Density: 1.0±0.1 g/cm3
Boiling Point: 417.9±33.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 67.1±3.0 kJ/mol
Flash Point: 183.7±22.3 °C
Index of Refraction: 1.586
Molar Refractivity: 97.1±0.3 cm3
#H bond acceptors: 1
#H bond donors: 0
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 1
ACD/LogP: 6.61
ACD/LogD (pH 5.5): 4.58
ACD/BCF (pH 5.5): 816.35
ACD/KOC (pH 5.5): 1663.77
ACD/LogD (pH 7.4): 5.89
ACD/BCF (pH 7.4): 16327.07
ACD/KOC (pH 7.4): 33275.59
Polar Surface Area: 3 Å2
Polarizability: 38.5±0.5 10-24cm3
Surface Tension: 41.1±3.0 dyne/cm
Molar Volume: 289.1±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) =  5.81

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  396.70  (Adapted Stein & Brown method)
    Melting Pt (deg C):  146.54  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.84E-007  (Modified Grain method)
    Subcooled liquid VP: 1E-005 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):  1.532
       log Kow used: 5.81 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.29898 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.85E-007  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.462E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.81  (KowWin est)
  Log Kaw used:  -5.121  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.931
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2196
   Biowin2 (Non-Linear Model)     :   0.0062
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0882  (months      )
   Biowin4 (Primary Survey Model) :   2.9858  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1068
   Biowin6 (MITI Non-Linear Model):   0.0064
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.6877
 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):  0.00133 Pa (1E-005 mm Hg)
  Log Koa (Koawin est  ): 10.931
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00225 
       Octanol/air (Koa) model:  0.0209 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0752 
       Mackay model           :  0.153 
       Octanol/air (Koa) model:  0.626 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 235.0818 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 244.9618 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.546 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.524 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.571750 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     1.140500 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     2.004 Days (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     1.005 Days (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.114 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  6.458E+005
      Log Koc:  5.810 

 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 = 3.773 (BCF = 5936)
       log Kow used: 5.81 (estimated)

 Volatilization from Water:
    Henry LC:  1.85E-007 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:       5405  hours   (225.2 days)
    Half-Life from Model Lake :  5.91E+004  hours   (2463 days)

 Removal In Wastewater Treatment:
    Total removal:              91.15  percent
    Total biodegradation:        0.76  percent
    Total sludge adsorption:    90.38  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       0.0142          1.07         1000       
   Water     3.74            1.44e+003    1000       
   Soil      40.7            2.88e+003    1000       
   Sediment  55.5            1.3e+004     0          
     Persistence Time: 3.47e+003 hr




                    

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