ChemSpider 2D Image | (±)-Felodipine | C18H19Cl2NO4

(±)-Felodipine

  • Molecular FormulaC18H19Cl2NO4
  • Average mass384.254 Da
  • Monoisotopic mass383.069122 Da
  • ChemSpider ID3216

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(±)-Felodipine
(±)-Felodipine
(RS)-Felodipine
3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, ethyl methyl ester [ACD/Index Name]
4-(2,3-Dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid ethyl methyl ester
4-(2,3-Dichlorophényl)-2,6-diméthyl-1,4-dihydro-3,5-pyridinedicarboxylate d'éthyle et de méthyle [French] [ACD/IUPAC Name]
4-(2,3-dichlorophényl)-2,6-diméthyl-1,4-dihydropyridine-3,5-dicarboxylate d'éthyle et de méthyle [French]
4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester
4877
72509-76-3 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AE-641/11429675 [DBID]
BRN 4331472 [DBID]
CGH-869 [DBID]
D00319 [DBID]
EU-0100508 [DBID]
F9677_SIGMA [DBID]
LS-131202 [DBID]
MLS000069629 [DBID]
Prestwick_797 [DBID]
Prestwick0_000478 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      22 LKT Labs [F1745]
      5 Axon Medchem 1448
      C08CA02 Wikidata Q420644
      H302 LKT Labs [F1745]
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1448
      no pictogram Axon Medchem 1448
      None LKT Labs [F1745]
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1448
      Warning Axon Medchem 1448
      Xn LKT Labs [F1745]
    • Target Organs:

      PDE inhibitor;Calcium Channel inhibitor;Calmodulin inhibitor TargetMol T0145
    • Chemical Class:

      Ca2+ Channel EU-OpenScreen [F 9677]
      The mixed (methyl, ethyl) diester of 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid. A calcium-channel blocker, it lowers blood pressure by reducing peripheral vascular resistance through a highly selective action on smooth muscle in arteriolar resistance vessels. It is used in the management of hypertension and angina pectoris. ChEBI CHEBI:585948
    • Drug Status:

      approved BIONET-Key Organics KS-1264
    • Bio Activity:

      Ca2+ channel blocker (L-type) Tocris Bioscience 2960
      Calcium Channel MedChem Express HY-B0309
      Calcium Channels Tocris Bioscience 2960
      Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase;Calcium Channel;Calmodulin TargetMol T0145
      Felodipine is a long-acting 1,4-dihydropyridine calcium channel blocker. MedChem Express
      Felodipine is a long-acting 1,4-dihydropyridine calcium channel blocker.; Target: Calcium Channel; Felodipine is a long-acting 1,4-dihydropyridine calcium channel blocker (CCB)b. MedChem Express HY-B0309
      Felodipine is a long-acting 1,4-dihydropyridine calcium channel blocker.;Target: Calcium ChannelFelodipine is a long-acting 1,4-dihydropyridine calcium channel blocker (CCB)b. It acts primarily on vascular smooth muscle cells by stabilizing voltage-gated L-type calcium channels in their inactive conformation. Felodipine significantly relaxes KCl-contracted porcine coronary segments by blocking the Ca2+ channels, displaying ~50 times more potent than nifedipine (IC50 of ~8 nM) and ~430 times than verapamil (IC50 of ~65 nM) [1]. Felodipine significantly induces the transcription and secretion of IL-6 and IL-8 with ED50 values of 5.8 nM and 5.3 nM in primary human VSMC and lung fibroblasts, respectively, while propranolol or furosemide fails to affect the expression of the two IL genes [2]. Felodipine blocks the muscarinic receptor-mediated (carbachol) Ca2+-dependent contraction of guinea pig ileum longitudinal smooth muscle (GPILSM) with an IC50 of 1.45 nM [3]. MedChem Express HY-B0309
      Ion Channels Tocris Bioscience 2960
      L-type Ca2+ channel blocker that is selective over N-, R-, P/Q- and T-type channels. Displays high vascular selectivity; lowers arterial blood pressure without altering cardiac contractility. Antihype rtensive. Tocris Bioscience 2960
      L-type Ca2+ channel blocker that is selective over N-, R-, P/Q- and T-type channels. Displays high vascular selectivity; lowers arterial blood pressure without altering cardiac contractility. Antihypertensive. Tocris Bioscience 2960
      Membrane Tranporter/Ion Channel MedChem Express HY-B0309
      Membrane Tranporter/Ion Channel; MedChem Express HY-B0309
      Metabolism;Membrane Transporter/Ion Channel TargetMol T0145
      Voltage-gated Calcium Channels Tocris Bioscience 2960
  • Gas Chromatography
    • Retention Index (Kovats):

      2815 (estimated with error: 89) NIST Spectra mainlib_352172, replib_247476, replib_247506, replib_379663
    • Retention Index (Normal Alkane):

      2678 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.53 mm; Column length: 12 m; Column type: Capillary; Heat rate: .5 K/min; Start T: 100 C; End T: 310 C; End time: 10 min; Start time: 2 min; CAS no: 72509763; Active phase: DB-5; Carrier gas: He; Phase thickness: 1.0 um; Data type: Normal alkane RI; Authors: Drummer, O.H.; Horomidis, S.; Kourtis, S.K.; Syrjanen, M.L.; Tippet, P., Capillary gas chromatographic drug screen for use in forensic toxicology, J. Anal. Toxicol., 18, 1994, 134-138.) NIST Spectra nist ri
    • Retention Index (Linear):

      2718.2 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: Multi-step temperature program; T(initial)=60C; T(final)=270C; CAS no: 72509763; Active phase: VF-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., 2008.) NIST Spectra nist ri

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

Density: 1.3±0.1 g/cm3
Boiling Point: 471.5±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 73.4±3.0 kJ/mol
Flash Point: 239.0±28.7 °C
Index of Refraction: 1.550
Molar Refractivity: 95.8±0.3 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 4.83
ACD/LogD (pH 5.5): 4.86
ACD/BCF (pH 5.5): 2918.77
ACD/KOC (pH 5.5): 10514.28
ACD/LogD (pH 7.4): 4.86
ACD/BCF (pH 7.4): 2923.59
ACD/KOC (pH 7.4): 10531.62
Polar Surface Area: 65 Å2
Polarizability: 38.0±0.5 10-24cm3
Surface Tension: 42.2±3.0 dyne/cm
Molar Volume: 300.8±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) =  4.46
    Log Kow (Exper. database match) =  3.86
       Exper. Ref:  Sangster (1994)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  433.25  (Adapted Stein & Brown method)
    Melting Pt (deg C):  166.84  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.4E-008  (Modified Grain method)
    Subcooled liquid VP: 1.28E-006 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):  19.71
       log Kow used: 3.86 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  51.162 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.35E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.129E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.86  (exp database)
  Log Kaw used:  -9.258  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.118
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7566
   Biowin2 (Non-Linear Model)     :   0.9667
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1668  (months      )
   Biowin4 (Primary Survey Model) :   3.3953  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3680
   Biowin6 (MITI Non-Linear Model):   0.0367
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1074
 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):  0.000171 Pa (1.28E-006 mm Hg)
  Log Koa (Koawin est  ): 13.118
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0176 
       Octanol/air (Koa) model:  3.22 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.388 
       Mackay model           :  0.584 
       Octanol/air (Koa) model:  0.996 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 114.2414 E-12 cm3/molecule-sec
      Half-Life =     0.094 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.124 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    14.787499 E-17 cm3/molecule-sec
      Half-Life =     0.077 Days (at 7E11 mol/cm3)
      Half-Life =      1.860 Hrs
   Fraction sorbed to airborne particulates (phi): 0.486 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.112E+004
      Log Koc:  4.046 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  4.024E-003  L/mol-sec
  Kb Half-Life at pH 8:       5.459  years  
  Kb Half-Life at pH 7:      54.586  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.272 (BCF = 187.2)
       log Kow used: 3.86 (expkow database)

 Volatilization from Water:
    Henry LC:  1.35E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.501E+007  hours   (3.542E+006 days)
    Half-Life from Model Lake : 9.274E+008  hours   (3.864E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              24.11  percent
    Total biodegradation:        0.27  percent
    Total sludge adsorption:    23.83  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       0.000115        1.02         1000       
   Water     8.69            1.44e+003    1000       
   Soil      89.5            2.88e+003    1000       
   Sediment  1.85            1.3e+004     0          
     Persistence Time: 2.89e+003 hr




                    

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