ChemSpider 2D Image | Latanoprost | C26H40O5

Latanoprost

  • Molecular FormulaC26H40O5
  • Average mass432.593 Da
  • Monoisotopic mass432.287567 Da
  • ChemSpider ID4470740
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 5 of 5 defined stereocentres


More details:



Featured data source



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

(5Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(3R)-3-hydroxy-5-phénylpentyl]cyclopentyl}-5-hepténoate d'isopropyle [French] [ACD/IUPAC Name]
(5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phénylpentyl]cyclopentyl}hept-5-énoate de 1-méthyléthyle
[1R-[1a(Z),2b(R*),3a,5a]]-7-[3,5-Dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl]-5-heptenoic Acid 1-Methylethyl Ester
13,14-Dihydro-17-phenyl-18,19,20-trinor-PGF2a-isopropyl Ester
130209-82-4 [RN]
155551-81-8 [RN]
1-methylethyl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate
1-Methylethyl-(5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoat
5-Heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-, 1-methylethyl ester, (5Z)- [ACD/Index Name]
6980
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:6384 [DBID]
XA 41 [DBID]
D00356 [DBID]
L1167_SIGMA [DBID]
PhXA 41 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      S01EE01 Wikidata Q634959
    • Chemical Class:

      A prostaglandin F<smallsub><stereo>alpha</stereo></smallsub> that is the isopropyl ester prodrug of latanoprost free acid. Used in the treatment of open-angle glaucoma and ocular hypertension. ChEBI CHEBI:6384
    • Bio Activity:

      7-TM Receptors Tocris Bioscience 4757
      FP prostaglandin receptor agonist; also exhibits agonist activity at EP1 and EP3 receptors Tocris Bioscience 4757
      FP prostaglandin receptor agonist; displays greater selectivity than prostanglandin F2? (Cat. No. 4214). Exhibits agonist activity at EP1 and EP3 receptors, but little-to-no effect at EP2, DP, IP and TP prostanoid receptors. Tocris Bioscience 4757
      FP prostaglandin receptor agonist; displays greater selectivity than prostanglandin F2? (Cat. No. 4214). Exhibits agonist activity at EP1 and EP3 receptors, but little-to-no effect at EP2, DP, IP and TP prostanoid receptors. Tocris Bioscience 4757
      FP prostaglandin receptor agonist; displays greater selectivity than prostanglandin F2alpha (Cat. No. 4214). Exhibits agonist activity at EP1 and EP3 receptors, but little-to-no effect at EP2, DP, IP and TP prostanoid receptors. Tocris Bioscience 4757
      Latanoprost is a prostaglandin F2a analogue used for controlling the progression of glaucoma or ocular hypertension. MedChem Express
      Latanoprost is a prostaglandin F2a analogue used for controlling the progression of glaucoma or ocular hypertension.; Target: Others; Latanoprost is an ester prodrug analogue of prostaglandin F2 alpha which effectively reduces intraocular pressure (IOP) by increasing uveoscleral outflow rather than altering conventional trabeculo-canalicular) aqueous outflow. MedChem Express HY-B0577
      Latanoprost is a prostaglandin F2a analogue used for controlling the progression of glaucoma or ocular hypertension.;Target: Latanoprost is an ester prodrug analogue of prostaglandin F2 alpha which effectively reduces intraocular pressure (IOP) by increasing uveoscleral outflow rather than altering conventional trabeculo-canalicular) aqueous outflow. The IOP-lowering effect of latanoprost lasts for 20 to 24 hours after a single dose, which allows a single daily dosage regimen. latanoprost is a potent IOP-lowering agent with a number of positive features including a single daily dosage regimen, a novel mechanism of action that enhances the IOP-lowering effect of contemporary agents, and a lack of systemic adverse effects. These properties suitably poise latanoprost for a prominent position in the management of patients with primary open-angle glaucoma and ocular hypertension [1]. Latanoprost has also shown significant additive effects when used in combination with one or more MedChem Express HY-B0577
      Others MedChem Express HY-B0577
      Prostanoid Receptors Tocris Bioscience 4757

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

Density: 1.1±0.1 g/cm3
Boiling Point: 583.8±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 91.8±3.0 kJ/mol
Flash Point: 188.3±23.6 °C
Index of Refraction: 1.538
Molar Refractivity: 123.6±0.3 cm3
#H bond acceptors: 5
#H bond donors: 3
#Freely Rotating Bonds: 14
#Rule of 5 Violations: 0
ACD/LogP: 3.65
ACD/LogD (pH 5.5): 4.11
ACD/BCF (pH 5.5): 787.09
ACD/KOC (pH 5.5): 4116.97
ACD/LogD (pH 7.4): 4.11
ACD/BCF (pH 7.4): 787.09
ACD/KOC (pH 7.4): 4116.97
Polar Surface Area: 87 Å2
Polarizability: 49.0±0.5 10-24cm3
Surface Tension: 43.4±3.0 dyne/cm
Molar Volume: 395.5±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) =  5.67

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  547.45  (Adapted Stein & Brown method)
    Melting Pt (deg C):  229.58  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.26E-015  (Modified Grain method)
    Subcooled liquid VP: 5.14E-013 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):  0.0274
       log Kow used: 5.67 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.751 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.32E-011  atm-m3/mole
   Group Method:   4.15E-019  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  6.773E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.67  (KowWin est)
  Log Kaw used:  -8.867  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.537
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.3747
   Biowin2 (Non-Linear Model)     :   0.9987
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8104  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7773  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5650
   Biowin6 (MITI Non-Linear Model):   0.1967
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6073
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  6.85E-011 Pa (5.14E-013 mm Hg)
  Log Koa (Koawin est  ): 14.537
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.38E+004 
       Octanol/air (Koa) model:  84.5 
   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 = 103.5052 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 111.1052 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.240 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.155 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    13.000000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    20.000000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     2.116 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     1.375 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    :  1.509E+004
      Log Koc:  4.179 

 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 = 2.018 (BCF = 104.3)
       log Kow used: 5.67 (estimated)

 Volatilization from Water:
    Henry LC:  3.32E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.668E+007  hours   (1.528E+006 days)
    Half-Life from Model Lake : 4.001E+008  hours   (1.667E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              90.08  percent
    Total biodegradation:        0.76  percent
    Total sludge adsorption:    89.33  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       0.0632          1.14         1000       
   Water     10.4            360          1000       
   Soil      44.3            720          1000       
   Sediment  45.2            3.24e+003    0          
     Persistence Time: 814 hr




                    

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