ChemSpider 2D Image | Exatecan | C24H22FN3O4

Exatecan

  • Molecular FormulaC24H22FN3O4
  • Average mass435.448 Da
  • Monoisotopic mass435.159424 Da
  • ChemSpider ID133194
  • defined stereocentres - 2 of 2 defined stereocentres


More details:






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

(1S,9S)-1-Amino-9-ethyl-5-fluor-9-hydroxy-4-methyl-1,2,3,9,12,15-hexahydro-10H,13H-benzo[de]pyrano[3',4':6,7]indolizino[1,2-b]chinolin-10,13-dion [German] [ACD/IUPAC Name]
(1S,9S)-1-Amino-9-éthyl-5-fluoro-9-hydroxy-4-méthyl-1,2,3,9,12,15-hexahydro-10H,13H-benzo[de]pyrano[3',4':6,7]indolizino[1,2-b]quinoléine-10,13-dione [French] [ACD/IUPAC Name]
(1S,9S)-1-Amino-9-ethyl-5-fluoro-9-hydroxy-4-methyl-1,2,3,9,12,15-hexahydro-10H,13H-benzo[de]pyrano[3',4':6,7]indolizino[1,2-b]quinoline-10,13-dione [ACD/IUPAC Name]
10H,13H-Benzo[de]pyrano[3',4':6,7]indolizino[1,2-b]quinoline-10,13-dione, 1-amino-9-ethyl-5-fluoro-1,2,3,9,12,15-hexahydro-9-hydroxy-4-methyl-, (1S,9S)- [ACD/Index Name]
171335-80-1 [RN]
7887
Exatecan [INN]
exatecán [French] [INN]
exatécan [French] [INN]
exatecanum [Latin] [INN]
More...

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

OC71PP0F89 [DBID]
DX 8951 [DBID]
DX-8951 [DBID]
UNII:OC71PP0F89 [DBID]
UNII-OC71PP0F89 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-13631
      Cell Cycle/DNA Damage; MedChem Express HY-13631
      Exatecan (DX-8951) is a totally synthetic analogue of the topoisomerase I-inhibitor camptothecin, which was synthesised to impart increased aqueous solubility, greater tumour efficacy, and less toxici ty than camptothecin itself. MedChem Express
      Exatecan (DX-8951) is a totally synthetic analogue of the topoisomerase I-inhibitor camptothecin, which was synthesised to impart increased aqueous solubility, greater tumour efficacy, and less toxicity than camptothecin itself.; IC50 value:; Target: topoisomerase I; Exatecan was given as i.v. MedChem Express HY-13631
      Exatecan (DX-8951) is a totally synthetic analogue of the topoisomerase I-inhibitor camptothecin, which was synthesised to impart increased aqueous solubility, greater tumour efficacy, and less toxicity than camptothecin itself.;IC50 value:;Target: topoisomerase IExatecan was given as i.v. infusion over 30 min at a dose of 0.5mg/m2 every day for five consecutive days, repeated every 21 days. Seventy-four percentage of cycles could be given without dose or schedule modification. The main toxicity was haematotoxicity with grade 3/4 neutropenia in 49%, grade 3/4 thrombocytopenia in 23%, and grade 3/4 anaemia in 15% of patients, respectively [1]. The most common drug-related toxicity was neutropenia. Non-hematologic toxicities were mostly mild to moderate; the most common were nausea, vomiting and anorexia. Plasma concentrations of DX-8951 (the anhydrous form of DX-8951f) were well described using a linear 2-compartment PK model. All concentrations and dose events were simultaneously MedChem Express HY-13631
      Topoisomerase MedChem Express HY-13631

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

Density: 1.5±0.1 g/cm3
Boiling Point: 818.4±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.1 mmHg at 25°C
Enthalpy of Vaporization: 124.7±3.0 kJ/mol
Flash Point: 448.7±34.3 °C
Index of Refraction: 1.735
Molar Refractivity: 113.6±0.4 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 1.81
ACD/LogD (pH 5.5): 0.27
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 7.32
ACD/LogD (pH 7.4): 1.59
ACD/BCF (pH 7.4): 8.88
ACD/KOC (pH 7.4): 152.63
Polar Surface Area: 106 Å2
Polarizability: 45.0±0.5 10-24cm3
Surface Tension: 80.9±5.0 dyne/cm
Molar Volume: 283.2±5.0 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) =  0.17

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  650.38  (Adapted Stein & Brown method)
    Melting Pt (deg C):  282.84  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.18E-018  (Modified Grain method)
    Subcooled liquid VP: 3.7E-015 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):  5
       log Kow used: 0.17 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  30166 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Esters
       Benzyl Amines
       Acrylamides
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.63E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.936E-019 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.17  (KowWin est)
  Log Kaw used:  -18.969  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.139
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1938
   Biowin2 (Non-Linear Model)     :   0.0017
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5785  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.4201  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0293
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.6473
 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):  4.93E-013 Pa (3.7E-015 mm Hg)
  Log Koa (Koawin est  ): 19.139
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6.08E+006 
       Octanol/air (Koa) model:  3.38E+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 = 295.5812 E-12 cm3/molecule-sec
      Half-Life =     0.036 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    26.054 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =   758.159973 E-17 cm3/molecule-sec
      Half-Life =     0.002 Days (at 7E11 mol/cm3)
      Half-Life =      2.177 Min
   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    :  3.52E+004
      Log Koc:  4.547 

 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: 0.17 (estimated)

 Volatilization from Water:
    Henry LC:  2.63E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.645E+017  hours   (1.936E+016 days)
    Half-Life from Model Lake : 5.068E+018  hours   (2.112E+017 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       1.14e-005       0.0348       1000       
   Water     52.8            4.32e+003    1000       
   Soil      47.1            8.64e+003    1000       
   Sediment  0.106           3.89e+004    0          
     Persistence Time: 1.53e+003 hr




                    

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