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ChemSpider 2D Image | fluvastatin | C24H26FNO4

fluvastatin

  • Molecular FormulaC24H26FNO4
  • Average mass411.466 Da
  • Monoisotopic mass411.184601 Da
  • ChemSpider ID393587
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 2 of 2 defined stereocentres


More details:






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

(±)-(3R*,5S*,6E)-7-[3-(p-fluorophenyl)-1-isopropylindol-2-yl]-3,5-dihydroxy-6-heptenoate
(3R,5S)-7-[3-(4-fluorophenyl)-1-propan-2-yl-2-indolyl]-3,5-dihydroxy-6-heptenoic acid
(3R,5S,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid
(3R,5S,6E)-7-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic acid [ACD/IUPAC Name]
(3R,5S,6E)-7-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid
(3R,5S,6E)-7-[3-(4-Fluorphenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxy-6-heptensäure [German] [ACD/IUPAC Name]
(3R,5S,6E)-rel-7-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic acid
6-Heptenoic acid, 7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-, (3R,5S,6E)- [ACD/Index Name]
Acide (3R,5S,6E)-7-[3-(4-fluorophényl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxy-6-hepténoïque [French] [ACD/IUPAC Name]
fluvastatin [Wiki]
More...

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

115 [DBID]
AIDS059823 [DBID]
AIDS-059823 [DBID]
CHEBI:5136 [DBID]
nchembio790-comp18 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      C10AA04 Wikidata Q417942
    • Chemical Class:

      A (6<stereo>E</stereo>)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1<element>H</element>-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid diastereoisomer in which the stereocentres <locant>beta</locant>- and <lo cant>delta</locant>- to the carboxy group have <stereo>R</stereo> and <stereo>S</stereo> configuration, respectively. The drug fluvastatin is an equimolar mixture of this compound and its enantiomer. ChEBI CHEBI:38565
      A (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid diastereoisomer in which the stereocentres beta- and delta- to the carboxy group have R and S configuration, respectively. The drug fluvastatin is an equimolar mixture of this compound and its enantiomer. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:38565
    • Therapeutical Effect:

      Anticholesteremic Agents,Antioxidants,Enzyme Inhibitors,Free Radical Scavengers Sean Ekins
    • Bio Activity:

      Fluvastatin (Leschol) inhibits HMG-CoA reductase activity with IC50 of 8 nM. MedChem Express
      Fluvastatin (Leschol) inhibits HMG-CoA reductase activity with IC50 of 8 nM.; IC50 value: 8 nM; Target: HMG-CoA reductase; Fluvastatin is a competitive inhibitor of hydroxymethylglutaryl-coenzyme A reductase (HMGCR), the enzyme that catalyzes the conversion of HMG-CoA to mevalonic acid, the rate-limiting step in cholesterol biosynthesis. MedChem Express HY-14664
      Fluvastatin (Leschol) inhibits HMG-CoA reductase activity with IC50 of 8 nM.;IC50 value: 8 nM;Target: HMG-CoA reductaseFluvastatin is a competitive inhibitor of hydroxymethylglutaryl-coenzyme A reductase (HMGCR), the enzyme that catalyzes the conversion of HMG-CoA to mevalonic acid, the rate-limiting step in cholesterol biosynthesis. Human hepatocellular carcinoma cell (HCC) studies indicate that Fluvastatin induces G2/M phase arrest. In the presence of Fluvastatin, HCC cells show a decrease of Bcl-2 and procaspase-9 expression, and an increase in Bax, cleaved caspase-3, and cytochrome c. Fluvastatin is antilipemic and is used to reduce plasma cholesterol levels and prevent cardiovascular disease. MedChem Express HY-14664
      HMG-CoA Reductase (HMGCR) MedChem Express HY-14664
      Metabolism/Protease MedChem Express HY-14664
      Metabolism/Protease; MedChem Express HY-14664

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

Density: 1.2±0.1 g/cm3
Boiling Point: 681.8±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 105.1±3.0 kJ/mol
Flash Point: 366.1±31.5 °C
Index of Refraction: 1.587
Molar Refractivity: 112.4±0.5 cm3
#H bond acceptors: 5
#H bond donors: 3
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 3.62
ACD/LogD (pH 5.5): 2.30
ACD/BCF (pH 5.5): 15.62
ACD/KOC (pH 5.5): 103.10
ACD/LogD (pH 7.4): 0.53
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.76
Polar Surface Area: 83 Å2
Polarizability: 44.5±0.5 10-24cm3
Surface Tension: 43.5±7.0 dyne/cm
Molar Volume: 334.2±7.0 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) =  4.85

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  592.52  (Adapted Stein & Brown method)
    Melting Pt (deg C):  255.82  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.91E-016  (Modified Grain method)
    Subcooled liquid VP: 6.28E-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):  0.4681
       log Kow used: 4.85 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  9.0823 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 :   5.58E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.209E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.85  (KowWin est)
  Log Kaw used:  -14.642  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.492
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1318
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5675  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.9120  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0346
   Biowin6 (MITI Non-Linear Model):   0.0002
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2268
 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):  8.37E-012 Pa (6.28E-014 mm Hg)
  Log Koa (Koawin est  ): 19.492
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.58E+005 
       Octanol/air (Koa) model:  7.62E+006 
   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 = 212.0817 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 219.6817 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.605 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.584 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    :  2649
      Log Koc:  3.423 

 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: 4.85 (estimated)

 Volatilization from Water:
    Henry LC:  5.58E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.128E+013  hours   (8.868E+011 days)
    Half-Life from Model Lake : 2.322E+014  hours   (9.675E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              72.39  percent
    Total biodegradation:        0.64  percent
    Total sludge adsorption:    71.75  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       0.00683         0.931        1000       
   Water     9.67            900          1000       
   Soil      74.4            1.8e+003     1000       
   Sediment  15.9            8.1e+003     0          
     Persistence Time: 1.9e+003 hr




                    

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