ChemSpider 2D Image | Topotecan | C23H23N3O5

Topotecan

  • Molecular FormulaC23H23N3O5
  • Average mass421.446 Da
  • Monoisotopic mass421.163757 Da
  • ChemSpider ID54705
  • defined stereocentres - 1 of 1 defined stereocentres


More details:



Featured data source



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

(4S)-10-[(Dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]chinolin-3,14(4H,12H)-dion [German] [ACD/IUPAC Name]
(4S)-10-[(Diméthylamino)méthyl]-4-éthyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoléine-3,14(4H,12H)-dione [French] [ACD/IUPAC Name]
(4S)-10-[(Dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione [ACD/IUPAC Name]
(S)-10-[(Dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]-quinoline-3,14(4H,12H)-dione
119413-54-6 [RN]
1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-, (4S)- [ACD/Index Name]
6783
7M7YKX2N15
9-[(Dimethylamino)methyl]-10-hydroxy-(20S)-camptothecin
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:63632 [DBID]
AIDS016393 [DBID]
AIDS-016393 [DBID]
C11158 [DBID]
NChemBio.2007.10-comp24 [DBID]
NCI60_004771 [DBID]
NCIStruc1_001659 [DBID]
NCIStruc2_001796 [DBID]
NSC609699 (HCL) [DBID]
NSC641007 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 090193
      L01XX17 Wikidata Q419953
    • Chemical Class:

      A pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single st rand breaks. ChEBI CHEBI:63632
    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-13768
      Cell Cycle/DNA Damage; MedChem Express HY-13768
      Topoisomerase MedChem Express HY-13768
      Topotecan (SKF104864) is a topoisomerase I inhibitor for chemotherapeutic agent. MedChem Express
      Topotecan (SKF104864) is a topoisomerase I inhibitor for chemotherapeutic agent.; Target: Topoisomerase I; Topotecan is a topoisomerase I inhibitor which is currently evaluated as an adjuvant agent for malignant glioma. MedChem Express HY-13768
      Topotecan (SKF104864) is a topoisomerase I inhibitor for chemotherapeutic agent.;Target: Topoisomerase I;Topotecan is a topoisomerase I inhibitor which is currently evaluated as an adjuvant agent for malignant glioma. Topotecan is a semisynthetic product derived from camptothecin, which was discovered during a National Cancer Institute cytotoxic drug screening program almost 30 years ago. Topotecan possesses a serum half-life of approximately 3 h, a high volume of distribution with high tissue uptake and a low protein binding. Results of phase II studies suggest considerable antitumor activity of single agent topotecan in small cell lung cancer and ovarian cancer patients. A randomized phase III trial of topotecan versus paclitaxel in ovarian cancer patients pretreated with cisplatin/cyclophosphamide has demonstrated that topotecan is as effective as paclitaxel in the second-line treatment of these patients. Activity of topotecan was also observed in non-small-cell lung cancer, refr MedChem Express HY-13768

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

Density: 1.5±0.1 g/cm3
Boiling Point: 782.9±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.8 mmHg at 25°C
Enthalpy of Vaporization: 119.5±3.0 kJ/mol
Flash Point: 427.3±32.9 °C
Index of Refraction: 1.734
Molar Refractivity: 112.7±0.4 cm3
#H bond acceptors: 8
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 1.08
ACD/LogD (pH 5.5): -0.82
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): 0.68
ACD/BCF (pH 7.4): 1.36
ACD/KOC (pH 7.4): 28.53
Polar Surface Area: 103 Å2
Polarizability: 44.7±0.5 10-24cm3
Surface Tension: 82.9±5.0 dyne/cm
Molar Volume: 281.3±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) =  -0.88

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  654.83  (Adapted Stein & Brown method)
    Melting Pt (deg C):  284.92  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.52E-018  (Modified Grain method)
    Subcooled liquid VP: 2.67E-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):  2350
       log Kow used: -0.88 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  15463 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.59E-024  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.306E-022 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.88  (KowWin est)
  Log Kaw used:  -22.187  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  21.307
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6579
   Biowin2 (Non-Linear Model)     :   0.6808
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9433  (months      )
   Biowin4 (Primary Survey Model) :   3.2723  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0345
   Biowin6 (MITI Non-Linear Model):   0.0045
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.5955
 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):  3.56E-013 Pa (2.67E-015 mm Hg)
  Log Koa (Koawin est  ): 21.307
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  8.43E+006 
       Octanol/air (Koa) model:  4.98E+008 
   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 = 264.2601 E-12 cm3/molecule-sec
      Half-Life =     0.040 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    29.142 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    63.180000 E-17 cm3/molecule-sec
      Half-Life =     0.018 Days (at 7E11 mol/cm3)
      Half-Life =     26.120 Min
   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    :  1.587E+004
      Log Koc:  4.201 

 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: -0.88 (estimated)

 Volatilization from Water:
    Henry LC:  1.59E-024 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  7.56E+020  hours   (3.15E+019 days)
    Half-Life from Model Lake : 8.247E+021  hours   (3.436E+020 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       1.27e-008       0.301        1000       
   Water     49.4            1.44e+003    1000       
   Soil      50.5            2.88e+003    1000       
   Sediment  0.0961          1.3e+004     0          
     Persistence Time: 1.17e+003 hr




                    

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