ChemSpider 2D Image | Pitavastatin | C25H24FNO4

Pitavastatin

  • Molecular FormulaC25H24FNO4
  • Average mass421.461 Da
  • Monoisotopic mass421.168945 Da
  • ChemSpider ID4445604
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 2 of 2 defined stereocentres


More details:



Featured data source



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

(3R,5S,6E)-7-(2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxyhept-6-enoic acid
(3R,5S,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid [ACD/IUPAC Name]
(3R,5S,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoic acid
(3R,5S,6E)-7-[2-Cyclopropyl-4-(4-fluorphenyl)-3-chinolinyl]-3,5-dihydroxy-6-heptensäure [German] [ACD/IUPAC Name]
6-Heptenoic acid, 7-(2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl)-3,5-dihydroxy-, (3R,5S,6E)-
6-Heptenoic acid, 7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-, (3R,5S,6E)- [ACD/Index Name]
7730
Acide (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophényl)-3-quinoléinyl]-3,5-dihydroxy-6-hepténoïque [French] [ACD/IUPAC Name]
Itabavastin
Itavastatin
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

NK 104 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      C10AA08 Wikidata Q412677
    • Chemical Class:

      A dihydroxy monocarboxylic acid that is (6<stereo>E</stereo>)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]hept-6-enoic acid in which the two hydroxy groups are located at positions 3 and 5 (the 3 <stereo>R</stereo>,5<stereo>S</stereo>-stereoisomer). Used as its calcium salt for treatment of hypercholesterolemia (elevated levels of cholesterol in the blood) on patients unable to sufficiently lo wer their cholesterol levels by diet and exercise. ChEBI CHEBI:32020
    • Bio Activity:

      HMG-CoA Reductase (HMGCR) MedChem Express HY-B0144A
      Metabolism/Protease MedChem Express HY-B0144A
      Metabolism/Protease; MedChem Express HY-B0144A
      Pitavastatin (NK-104) is a potent HMG-CoA reductase inhibitor, Pitavastatin inhibited cholesterol synthesis from acetic acid with an IC50 of 5.8 nM in a human liver cancer cell line (HepG2). MedChem Express
      Pitavastatin (NK-104) is a potent HMG-CoA reductase inhibitor, Pitavastatin inhibited cholesterol synthesis from acetic acid with an IC50 of 5.8 nM in a human liver cancer cell line (HepG2).; IC50 value: 5.8 nM(cholesterol synthesis from acetic; acid in HepG2) [1]; Target: HMG-CoA reductase; in vitro: Pitavastatin inhibited cholesterol synthesis from acetic; acid with an IC50 of 5.8 nM in a human liver cancer cell line (HepG2), which indicates that is 2.9 and 5.7 times as potent as simvastatin and atorvastatin, respectively. MedChem Express HY-B0144A
      Pitavastatin (NK-104) is a potent HMG-CoA reductase inhibitor, Pitavastatin inhibited cholesterol synthesis from acetic acid with an IC50 of 5.8 nM in a human liver cancer cell line (HepG2).;IC50 value: 5.8 nM(cholesterol synthesis from aceticacid in HepG2) [1];Target: HMG-CoA reductase;In vitro: Pitavastatin inhibited cholesterol synthesis from aceticacid with an IC50 of 5.8 nM in a human liver cancer cell line (HepG2), which indicates that is 2.9 and 5.7 times as potent as simvastatin and atorvastatin, respectively. When the inhibitory activity interms of the ED50 was compared with that of simvastatin,pitavastatin showed a 3-fold stronger activity in the rat and 15-fold stronger activity in a guinea pig model.22 The inhibitory effect of pitavastatin on sterol synthesis is thought to be liver-selective [1]. pitavastatin reduces total and phosphorylated tau levels in a cellular model of tauopathy, and in primary neuronal cultures. The decrease caused by pitavastatin is revers MedChem Express HY-B0144A

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

Density: 1.4±0.1 g/cm3
Boiling Point: 692.0±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.3 mmHg at 25°C
Enthalpy of Vaporization: 106.5±3.0 kJ/mol
Flash Point: 372.3±31.5 °C
Index of Refraction: 1.680
Molar Refractivity: 117.8±0.3 cm3
#H bond acceptors: 5
#H bond donors: 3
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 3.45
ACD/LogD (pH 5.5): 2.09
ACD/BCF (pH 5.5): 10.35
ACD/KOC (pH 5.5): 73.31
ACD/LogD (pH 7.4): 0.38
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.44
Polar Surface Area: 91 Å2
Polarizability: 46.7±0.5 10-24cm3
Surface Tension: 64.8±3.0 dyne/cm
Molar Volume: 311.7±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) =  4.82

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  616.22  (Adapted Stein & Brown method)
    Melting Pt (deg C):  266.89  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.32E-017  (Modified Grain method)
    Subcooled liquid VP: 1.05E-014 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):  0.4256
       log Kow used: 4.82 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  64.354 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Vinyl/Allyl Alcohols-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.89E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.023E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.82  (KowWin est)
  Log Kaw used:  -16.393  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  21.213
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1817
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4705  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.8291  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0844
   Biowin6 (MITI Non-Linear Model):   0.0003
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2232
 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):  1.4E-012 Pa (1.05E-014 mm Hg)
  Log Koa (Koawin est  ): 21.213
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.14E+006 
       Octanol/air (Koa) model:  4.01E+008 
   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 =  96.4999 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 104.0999 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.330 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.233 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     6.825000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    13.650000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     4.030 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     2.015 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   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    :  5836
      Log Koc:  3.766 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 4.82 (estimated)

 Volatilization from Water:
    Henry LC:  9.89E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.215E+015  hours   (5.064E+013 days)
    Half-Life from Model Lake : 1.326E+016  hours   (5.524E+014 days)

 Removal In Wastewater Treatment:
    Total removal:              71.19  percent
    Total biodegradation:        0.63  percent
    Total sludge adsorption:    70.56  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       0.000979        1.6          1000       
   Water     9.02            900          1000       
   Soil      77.1            1.8e+003     1000       
   Sediment  13.9            8.1e+003     0          
     Persistence Time: 2.1e+003 hr




                    

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