ChemSpider 2D Image | Panobinostat | C21H23N3O2

Panobinostat

  • Molecular FormulaC21H23N3O2
  • Average mass349.426 Da
  • Monoisotopic mass349.179016 Da
  • ChemSpider ID5294028
  • Double-bond stereo - Double-bond stereo


More details:



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

(2E)-N-Hydroxy-3-[4-({[2-(2-methyl-1H-indol-3-yl)ethyl]amino}methyl)phenyl]acrylamid [German] [ACD/IUPAC Name]
(2E)-N-Hydroxy-3-[4-({[2-(2-methyl-1H-indol-3-yl)ethyl]amino}methyl)phenyl]acrylamide [ACD/IUPAC Name]
(2E)-N-Hydroxy-3-[4-({[2-(2-méthyl-1H-indol-3-yl)éthyl]amino}méthyl)phényl]acrylamide [French] [ACD/IUPAC Name]
(2E)-N-hydroxy-3-[4-({[2-(2-methyl-1H-indol-3-yl)ethyl]amino}methyl)phenyl]prop-2-enamide
(E)-N-HYDROXY-3-(4-{[2-(2-METHYL-1H-INDOL-3-YL)-ETHYLAMINO]-METHYL}-PHENYL)-ACRYLAMIDE
2-Propenamide, N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-, (2E)- [ACD/Index Name]
404950-80-7 [RN]
8805
Farydak [Trade name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

9647FM7Y3Z [DBID]
CCRIS 4693 [DBID]
PubChem Substance ID 24856928 [DBID]
UNII:9647FM7Y3Z [DBID]
UNII-9647FM7Y3Z [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      Yellow Powder Novochemy [NC-31098]
      yellow solid Novochemy [NC-31098]
    • Safety:

      20/21/22 Novochemy [NC-31098]
      20/21/36/37/39 Novochemy [NC-31098]
      5 Axon Medchem 1548
      GHS07; GHS09 Novochemy [NC-31098]
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1548
      H332; H403 Novochemy [NC-31098]
      IRRITANT Matrix Scientific 090480
      no pictogram Axon Medchem 1548
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1548
      P301+P310; P337+P313 Novochemy [NC-31098]
      R22 Novochemy [NC-31098]
      Warning Novochemy [NC-31098]
      Warning Axon Medchem 1548
    • Chemical Class:

      A hydroxamic acid obtained by formal condensation of the carboxy group of (2<stereo>E</stereo>)-3-[4-({[2-(2-methylindol-3-yl)ethyl]amino}methyl)phenyl]prop-2-enoic acid with the amino group of hydrox ylamine. A histone deacetylase inhibitor used (as its lactate salt) in combination with bortezomib and dexamethasone for the treatment of multiple myeloma. ChEBI CHEBI:85990
    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-10224
      Cell Cycle/DNA Damage; MedChem Express HY-10224
      HDAC MedChem Express HY-10224
      Panobinostat(LBH-589) is a broad-spectrum HDAC inhibitor; low nanomolar concentrations (IC50=5-20 nM) of LBH589 induced cell-cycle arrest, apoptosis, and histone (H3K9 and H4K8) hyperacetylation in MOLT-4 and Reh cell.; IC50 Value: ~5 nM(MOLT-4 cell); ~20 nM(Reh cell); Target: HDAC; in vitro: LBH589 induces apoptosis among MOLT-4 and Reh cells in a time- and dose-dependent manner. MedChem Express HY-10224
      Panobinostat(LBH-589) is a broad-spectrum HDAC inhibitor; low nanomolar concentrations (IC50=5-20 nM) of LBH589 induced cell-cycle arrest, apoptosis, and histone (H3K9 and H4K8) hyperacetylation in MOLT-4 and Reh cell.;IC50 Value: ~5 nM(MOLT-4 cell); ~20 nM(Reh cell);Target: HDAC;In vitro: LBH589 induces apoptosis among MOLT-4 and Reh cells in a time- and dose-dependent manner. Moreover, LBH589 is more potent in MOLT-4 than in Reh cells. LBH589 markedly prevents the growth of both MOLT-4 and Reh cells in a dose-dependent manner at 48 hours. LBH589 treatment causes a 2- to 3-fold increase in the number of cells in the G2/M phase of the cell cycle compared with the control cells. LBH589 is associated with induction of histone H3K9 and histone H4K8 acetylation as well as decreasing levels of c-Myc expression in a dose-dependent manner. LBH589 treatment also increases the levels of p21 expression. LBH589 treatment also decreases the levels of c-Myc after an initial increase at the lowe MedChem Express HY-10224

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

Density: 1.2±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.683
Molar Refractivity: 106.7±0.3 cm3
#H bond acceptors: 5
#H bond donors: 4
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 3.62
ACD/LogD (pH 5.5): 0.00
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): 1.05
ACD/BCF (pH 7.4): 1.24
ACD/KOC (pH 7.4): 11.08
Polar Surface Area: 77 Å2
Polarizability: 42.3±0.5 10-24cm3
Surface Tension: 58.3±3.0 dyne/cm
Molar Volume: 281.4±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) =  2.69

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  608.15  (Adapted Stein & Brown method)
    Melting Pt (deg C):  263.12  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2E-016  (Modified Grain method)
    Subcooled liquid VP: 8.13E-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):  31.38
       log Kow used: 2.69 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  127.32 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.56E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.930E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.69  (KowWin est)
  Log Kaw used:  -18.980  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  21.670
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8444
   Biowin2 (Non-Linear Model)     :   0.5771
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3017  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.2498  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2365
   Biowin6 (MITI Non-Linear Model):   0.0018
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3720
 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):  1.08E-011 Pa (8.13E-014 mm Hg)
  Log Koa (Koawin est  ): 21.670
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.77E+005 
       Octanol/air (Koa) model:  1.15E+009 
   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 = 313.4502 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 316.1102 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =   24.569 Min (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =   24.362 Min (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.050000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     2.100000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     1.091 Days (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =   785.828 Min (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    :  1.996E+006
      Log Koc:  6.300 

 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 = 1.373 (BCF = 23.59)
       log Kow used: 2.69 (estimated)

 Volatilization from Water:
    Henry LC:  2.56E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.275E+017  hours   (1.781E+016 days)
    Half-Life from Model Lake : 4.664E+018  hours   (1.943E+017 days)

 Removal In Wastewater Treatment:
    Total removal:               3.77  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.66  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       4.06e-007       0.794        1000       
   Water     14.5            900          1000       
   Soil      85.4            1.8e+003     1000       
   Sediment  0.171           8.1e+003     0          
     Persistence Time: 1.71e+003 hr




                    

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