ChemSpider 2D Image | Mitoxantrone | C22H28N4O6

Mitoxantrone

  • Molecular FormulaC22H28N4O6
  • Average mass444.481 Da
  • Monoisotopic mass444.200897 Da
  • ChemSpider ID4067

More details:



Featured data source



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

Mitoxanthrone
1,4-Dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)-9,10-anthrachinon [German] [ACD/IUPAC Name]
1,4-Dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)-9,10-anthraquinone [ACD/IUPAC Name]
1,4-Dihydroxy-5,8-bis({2-[(2-hydroxyéthyl)amino]éthyl}amino)-9,10-anthraquinone [French] [ACD/IUPAC Name]
1,4-Dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)anthracen-9,10-dion
1,4-dihydroxy-5,8-bis({2-[(2-hydroxyéthyl)amino]éthyl}amino)anthracène-9,10-dione
1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione
1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthraquinone
4922
65271-80-9 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS005213 [DBID]
AIDS-005213 [DBID]
BRN 2795126 [DBID]
C11195 [DBID]
CCRIS 7604 [DBID]
CL-232315 [DBID]
DivK1c_000516 [DBID]
KBio1_000516 [DBID]
KBio2_002135 [DBID]
KBio2_004703 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      L01DB07 Wikidata Q239426
    • Chemical Class:

      A dihydroxyanthraquinone that is 1,4-dihydroxy-9,10-anthraquinone which is substituted by 6-hydroxy-1,4-diazahexyl groups at positions 5 and 8. ChEBI CHEBI:50729
    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-13502
      Cell Cycle/DNA Damage; MedChem Express HY-13502
      Mitoxantrone, a type II topoisomerase inhibitor, is an anthracenedione-derived antineoplastic agent. MedChem Express
      Mitoxantrone, a type II topoisomerase inhibitor, is an anthracenedione-derived antineoplastic agent.; Target: Topoisomerase II; Mitoxantrone is an anthracenedione antineoplastic agent. MedChem Express HY-13502
      Mitoxantrone, a type II topoisomerase inhibitor, is an anthracenedione-derived antineoplastic agent.;Target: Topoisomerase IIMitoxantrone is an anthracenedione antineoplastic agent. Mitoxantrone is a type II topoisomerase inhibitor; it disrupts DNA synthesis and DNA repair in both healthy cells and cancer cells, by intercalation [1]. Mitoxantrone is used in the treatment of certain types of cancer, mostly metastatic breast cancer, acute myeloid leukemia, and non-Hodgkin's lymphoma. It was also shown to improve the survival of children suffering from first relapse of acute lymphoblastic leukaemia [2]. Mitoxantrone is also used to treat multiple sclerosis (MS), most notably the subset known as secondary progressive MS. Mitoxantrone will not cure multiple sclerosis, but is effective in slowing the progression of secondary progressive MS and extending the time between relapses in relapsing-remitting MS and progressive relapsing MS [3]. MedChem Express HY-13502
      Topoisomerase MedChem Express HY-13502
  • Gas Chromatography

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

Density: 1.5±0.1 g/cm3
Boiling Point: 805.7±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.0 mmHg at 25°C
Enthalpy of Vaporization: 122.8±3.0 kJ/mol
Flash Point: 441.1±34.3 °C
Index of Refraction: 1.709
Molar Refractivity: 119.7±0.3 cm3
#H bond acceptors: 10
#H bond donors: 8
#Freely Rotating Bonds: 12
#Rule of 5 Violations: 2
ACD/LogP: 0.45
ACD/LogD (pH 5.5): -2.35
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.19
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 163 Å2
Polarizability: 47.5±0.5 10-24cm3
Surface Tension: 84.5±3.0 dyne/cm
Molar Volume: 306.5±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) =  2.28

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  699.76  (Adapted Stein & Brown method)
    Melting Pt (deg C):  305.91  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.25E-020  (Modified Grain method)
    Subcooled liquid VP: 1.75E-017 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):  54.85
       log Kow used: 2.28 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Phenols
       Quinone/Hydroquinone

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.96E-030  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.333E-022 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.28  (KowWin est)
  Log Kaw used:  -27.546  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  29.826
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9388
   Biowin2 (Non-Linear Model)     :   0.1480
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3836  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3701  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2554
   Biowin6 (MITI Non-Linear Model):   0.0085
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1044
 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):  2.33E-015 Pa (1.75E-017 mm Hg)
  Log Koa (Koawin est  ): 29.826
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.29E+009 
       Octanol/air (Koa) model:  1.64E+017 
   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 = 234.3751 E-12 cm3/molecule-sec
      Half-Life =     0.046 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.548 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   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    :  64.89
      Log Koc:  1.812 

 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 = -0.435 (BCF = 0.3675)
       log Kow used: 2.28 (estimated)

 Volatilization from Water:
    Henry LC:  6.96E-030 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.774E+026  hours   (7.39E+024 days)
    Half-Life from Model Lake : 1.935E+027  hours   (8.061E+025 days)

 Removal In Wastewater Treatment:
    Total removal:               2.60  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.51  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       7.31e-012       1.1          1000       
   Water     18.6            900          1000       
   Soil      81.3            1.8e+003     1000       
   Sediment  0.105           8.1e+003     0          
     Persistence Time: 1.56e+003 hr




                    

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