ChemSpider 2D Image | Amsacrine | C21H19N3O3S

Amsacrine

  • Molecular FormulaC21H19N3O3S
  • Average mass393.459 Da
  • Monoisotopic mass393.114716 Da
  • ChemSpider ID2094

More details:

Featured data source
The Merck Index Online

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

257-094-3 [EINECS]
4'-(Acridinylamino)methanesulfon-m-anisidide
51264-14-3 [RN]
AMSA, M-
Amsacrina [Spanish] [INN]
Amsacrine [BAN] [INN] [USAN] [Wiki]
Amsacrinum [Latin]
Methanesulfonamide, N-(4-(9-acridinylamino)-3-methoxyphenyl)-
Methanesulfonamide, N-[4-(9-acridinylamino)-3-methoxyphenyl]- [ACD/Index Name]
MFCD00242748 [MDL number]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

00DPD30SOY [DBID]
4864 [DBID]
SN 11841 [DBID]
AIDS001997 [DBID]
AIDS-001997 [DBID]
AMSA;m-AMSA;CI-880;SN-11841;acridinyl anisidide [DBID]
BRN 0500176 [DBID]
C01553 [DBID]
CCRIS 1027 [DBID]
CHEBI:2687 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Ether; Amide; Drug; Antineoplastic Agent; Metabolite; Synthetic Compound; Intercalating Agent Toxin, Toxin-Target Database T3D4674

    • Safety:

      L01XX01 Wikidata Q2784004

    • Target Organs:

      Potassium Channel inhibitor; Topoisomerase inhibitor TargetMol T1206

    • Chemical Class:

      A sulfonamide that is <element>N</element>-phenylmethanesulfonamide substituted by a methoxy group at position 3 and an acridin-9-ylamino group at position 4. It exhibits antineoplastic activity. ChEBI CHEBI:2687
      A sulfonamide that is N-phenylmethanesulfonamide substituted by a methoxy group at position 3 and an acridin-9-ylamino group at position 4. It exhibits antineoplastic activity. ChEBI CHEBI:2687

    • Bio Activity:

      Amsacrine (mAMSA) an antineoplastic agent which can intercalate into the DNA of tumor cells. MedChem Express http://www.medchemexpress.com/Amsacrine.html, HY-13551
      Amsacrine (mAMSA) an antineoplastic agent which can intercalate into the DNA of tumor cells. Amsacrine also expresses topoisomerase inhibitor activity, specifically inhibiting topoisomerase II.;IC50 value: ;Target: DNA intercalator; Topo II;In vitro: Amsacrine attenuated cell invasion with decreased MMP-2/MMP-9 protein expression and mRNA levels in U937, Jurkat, HL-60, K562, KU812 and MEG-01 cells. Moreover, amsacrine reduced both MMP-2/MMP-9 promoter luciferase activity and MMP-2/MMP-9 mRNA stability in leukemia cells.Studies on amsacrine-treated U937 cells revealed that amsacrine-elicited ROS generation induced JNK and p38 MAPK activation but reduced the phospho-ERK level. Amsacrine-induced ERK inactivation and p38 MAPK/JNK activation were demonstrated to suppress MMP-2/MMP-9 promoter luciferase activity and promote MMP-2/MMP-9 mRNA decay, respectively [1]. Amsacrine blocked HERG currents in HEK 293 cells and Xenopus oocytes in a concentration-dependent manner, with IC50 values o MedChem Express HY-13551
      Cell Cycle/DNA Damage MedChem Express HY-13551
      Cell Cycle/DNA Damage; MedChem Express HY-13551
      DNA Damage/DNA Repair TargetMol T1206
      Potassium Channel;topoisomerase II TargetMol T1206
      Topoisomerase MedChem Express HY-13551
  • Gas Chromatography

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.4±0.1 g/cm3
Boiling Point: 563.0±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 84.6±3.0 kJ/mol
Flash Point: 294.3±32.9 °C
Index of Refraction: 1.723
Molar Refractivity: 111.5±0.4 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 2.12
ACD/LogD (pH 5.5): 2.29
ACD/BCF (pH 5.5): 19.67
ACD/KOC (pH 5.5): 161.48
ACD/LogD (pH 7.4): 3.10
ACD/BCF (pH 7.4): 126.54
ACD/KOC (pH 7.4): 1038.98
Polar Surface Area: 89 Å2
Polarizability: 44.2±0.5 10-24cm3
Surface Tension: 65.7±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) =  3.89

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  578.73  (Adapted Stein & Brown method)
    Melting Pt (deg C):  249.37  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.44E-012  (Modified Grain method)
    MP  (exp database):  235 deg C
    Subcooled liquid VP: 2.64E-010 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):  0.1236
       log Kow used: 3.89 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  21.074 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.68E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.032E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.89  (KowWin est)
  Log Kaw used:  -14.163  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.053
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4584
   Biowin2 (Non-Linear Model)     :   0.0965
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1366  (months      )
   Biowin4 (Primary Survey Model) :   3.2488  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.3297
   Biowin6 (MITI Non-Linear Model):   0.0006
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4726
 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):  3.52E-008 Pa (2.64E-010 mm Hg)
  Log Koa (Koawin est  ): 18.053
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  85.2 
       Octanol/air (Koa) model:  2.77E+005 
   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 = 401.8904 E-12 cm3/molecule-sec
      Half-Life =     0.027 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    19.162 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  2.825E+005
      Log Koc:  5.451 

 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 = 2.298 (BCF = 198.4)
       log Kow used: 3.89 (estimated)

 Volatilization from Water:
    Henry LC:  1.68E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.913E+012  hours   (2.88E+011 days)
    Half-Life from Model Lake : 7.541E+013  hours   (3.142E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              25.31  percent
    Total biodegradation:        0.28  percent
    Total sludge adsorption:    25.02  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       2.98e-006       0.639        1000       
   Water     8.63            1.44e+003    1000       
   Soil      89.4            2.88e+003    1000       
   Sediment  1.97            1.3e+004     0          
     Persistence Time: 2.9e+003 hr

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