ChemSpider 2D Image | Tafluprost | C25H34F2O5

Tafluprost

  • Molecular FormulaC25H34F2O5
  • Average mass452.531 Da
  • Monoisotopic mass452.237427 Da
  • ChemSpider ID8044182
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 4 of 4 defined stereocentres


More details:



Featured data source



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

(5Z)-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-Difluoro-4-phénoxy-1-butén-1-yl]-3,5-dihydroxycyclopentyl}-5-hepténoate d'isopropyle [French] [ACD/IUPAC Name]
1O6WQ6T7G3
209860-87-7 [RN]
5-Heptenoic acid, 7-[(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-, 1-methylethyl ester, (5Z)- [ACD/Index Name]
8374
Isopropyl (5Z)-7-{(1R,2R,3R,5S)-2-((1E)-3,3-difluoro-4-phenoxybut-1-enyl)-3,5-dihydroxycyclopentyl}hept-5-enoate
Isopropyl (5Z)-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl}-5-heptenoate [ACD/IUPAC Name]
Isopropyl-(5Z)-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-difluor-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl}-5-heptenoat [German] [ACD/IUPAC Name]
Saflutan
Taflotan
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AFP-168 [DBID]
DE-085 [DBID]
MK-2452 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      S01EE05 Wikidata Q2139543
    • Chemical Class:

      A prostaglandin F<smallsub><stereo>alpha</stereo></smallsub> that is prostaglandin F<smallsub>2<stereo>alpha</stereo></smallsub> in which the carboxylic acid function has been converted to the corresp onding isopropyl ester and the 3-hydroxy-1-octenyl side-chain is substituted by 3,3-difluoro-4-phenoxybut-1-enyl. Used for treatment of elevated intraocular pressure in patients with open-angle glauco ma or ocular hypertension. ChEBI CHEBI:66899
    • Bio Activity:

      Others MedChem Express HY-B0600
      Tafluprost(AFP-168) is an anti-glaucoma prostaglandin (PG) analog.; Target:Others; Tafluprost showed significant IOP-lowering effects without any safety concerns in patients with various types of glaucoma and OH in daily clinical practice and tafluprost is highly effective in any therapeutic patterns [1]. MedChem Express HY-B0600
      Tafluprost(AFP-168) is an anti-glaucoma prostaglandin (PG) analog.;Target:;Tafluprost showed significant IOP-lowering effects without any safety concerns in patients with various types of glaucoma and OH in daily clinical practice and tafluprost is highly effective in any therapeutic patterns [1]. Tafluprost with reduced BAK has potential as a superior antiglaucoma drug, not only for its IOP-lowering effect, but also for its good corneal safety profile [2]. Tafluprost single-use vials treatment was effective in reducing IOP over the 3 years of this study, but visual field performance worsened by 10.3%-13.8% in patients with normal-tension glaucoma. Safety was satisfactory [3]. MedChem Express HY-B0600

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

Density: 1.2±0.1 g/cm3
Boiling Point: 552.9±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 87.7±3.0 kJ/mol
Flash Point: 288.2±30.1 °C
Index of Refraction: 1.549
Molar Refractivity: 121.3±0.3 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 13
#Rule of 5 Violations: 0
ACD/LogP: 4.23
ACD/LogD (pH 5.5): 4.24
ACD/BCF (pH 5.5): 987.32
ACD/KOC (pH 5.5): 4842.10
ACD/LogD (pH 7.4): 4.24
ACD/BCF (pH 7.4): 987.32
ACD/KOC (pH 7.4): 4842.10
Polar Surface Area: 76 Å2
Polarizability: 48.1±0.5 10-24cm3
Surface Tension: 40.8±3.0 dyne/cm
Molar Volume: 381.5±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) =  6.51

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  509.44  (Adapted Stein & Brown method)
    Melting Pt (deg C):  204.56  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.79E-013  (Modified Grain method)
    Subcooled liquid VP: 3.01E-011 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):  0.003928
       log Kow used: 6.51 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.034251 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.27E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.745E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.51  (KowWin est)
  Log Kaw used:  -8.285  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.795
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0998
   Biowin2 (Non-Linear Model)     :   0.9946
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4110  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6113  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6620
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4069
 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):  4.01E-009 Pa (3.01E-011 mm Hg)
  Log Koa (Koawin est  ): 14.795
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  748 
       Octanol/air (Koa) model:  153 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 146.8981 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 160.2741 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.874 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.801 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    13.568750 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    21.137501 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     2.027 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     1.301 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5038
      Log Koc:  3.702 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.141E-002  L/mol-sec
  Kb Half-Life at pH 8:       1.026  years  
  Kb Half-Life at pH 7:      10.259  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 4.316 (BCF = 2.069e+004)
       log Kow used: 6.51 (estimated)

 Volatilization from Water:
    Henry LC:  1.27E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.807E+006  hours   (4.086E+005 days)
    Half-Life from Model Lake :  1.07E+008  hours   (4.458E+006 days)

 Removal In Wastewater Treatment:
    Total removal:              93.45  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    92.67  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       0.0149          0.938        1000       
   Water     2.63            900          1000       
   Soil      31.2            1.8e+003     1000       
   Sediment  66.2            8.1e+003     0          
     Persistence Time: 2.87e+003 hr




                    

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