ChemSpider 2D Image | Amifostine | C5H15N2O3PS

Amifostine

  • Molecular FormulaC5H15N2O3PS
  • Average mass214.223 Da
  • Monoisotopic mass214.054092 Da
  • ChemSpider ID2056

More details:



Featured data source



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

20537-88-6 [RN]
4941
Acide ((amino-3 propylamino)-2 ethyl)-S-phosphorothioique [French]
amifostina [Spanish] [INN]
AMIFOSTINE ANHYDROUS
amifostinum [Latin]
dihydrogène thiophosphate de S-{2-[(3-aminopropyl)amino]éthyle}
Dihydrogénophosphorothioate de S-{2-[(3-aminopropyl)amino]éthyle} [French] [ACD/IUPAC Name]
Ethanethiol, 2-[(3-aminopropyl)amino]-, dihydrogen phosphate (ester) [ACD/Index Name]
More...

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

YM 08310 [DBID]
A5922_SIGMA [DBID]
AIDS041359 [DBID]
AIDS-041359 [DBID]
AU-95722 [DBID]
BRN 2088122 [DBID]
C06819 [DBID]
DivK1c_006743 [DBID]
EU-0100029 [DBID]
KBio1_001687 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      H302 LKT Labs [A4933]
      None LKT Labs [A4933]
      R22 LKT Labs [A4933]
      V03AF05 Wikidata Q251698
      Xn LKT Labs [A4933]
    • Chemical Class:

      An organic thiophosphate that is the <element>S</element>-phospho derivative of 2-[(3-aminopropyl)amino]ethanethiol. A prodrug for the free thiol, WR-1065, which is used as a cytoprotectant in cancer chemotherapy and radiotherapy. ChEBI CHEBI:2636
    • Therapeutical Effect:

      radioprotectant Microsource [01503081]
    • Drug Status:

      USP, INN, BAN Microsource [01503081]
    • Compound Source:

      synthetic Microsource [01503081]
    • Bio Activity:

      Amifostine is a cytoprotective adjuvant used in cancer chemotherapy and radiotherapy involving DNA-binding chemotherapeutic agents. MedChem Express
      Amifostine is a cytoprotective adjuvant used in cancer chemotherapy and radiotherapy involving DNA-binding chemotherapeutic agents.; Target: Others; Amifostine has been shown to specifically protect normal tissues from damage caused by radiation and chemotherapy. MedChem Express HY-B0639
      Amifostine is a cytoprotective adjuvant used in cancer chemotherapy and radiotherapy involving DNA-binding chemotherapeutic agents.;Target: Amifostine has been shown to specifically protect normal tissues from damage caused by radiation and chemotherapy. An inactive prodrug, amifostine is converted to an active thiol by dephosphorylation by alkaline phosphatase in the normal endothelium. The cytoprotective mechanism of amifostine is complicated, involving free-radical scavenging, DNA protection and repair acceleration, and induction of cellular hypoxia. amifostine has potential applications in many other oncologic settings [1]. MedChem Express HY-B0639
      Others MedChem Express HY-B0639

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

Density: 1.4±0.1 g/cm3
Boiling Point: 441.7±51.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.3 mmHg at 25°C
Enthalpy of Vaporization: 76.6±6.0 kJ/mol
Flash Point: 220.9±30.4 °C
Index of Refraction: 1.555
Molar Refractivity: 50.3±0.3 cm3
#H bond acceptors: 5
#H bond donors: 5
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 1
ACD/LogP: -1.68
ACD/LogD (pH 5.5): -4.31
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.35
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 131 Å2
Polarizability: 19.9±0.5 10-24cm3
Surface Tension: 64.6±3.0 dyne/cm
Molar Volume: 156.7±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) =  -1.07

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  400.36  (Adapted Stein & Brown method)
    Melting Pt (deg C):  86.28  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.1E-009  (Modified Grain method)
    MP  (exp database):  160.5 dec deg C
    Subcooled liquid VP: 7.61E-008 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):  1e+006
       log Kow used: -1.07 (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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.26E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.738E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.07  (KowWin est)
  Log Kaw used:  -17.528  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.458
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9532
   Biowin2 (Non-Linear Model)     :   0.8990
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7747  (weeks       )
   Biowin4 (Primary Survey Model) :   3.6252  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3885
   Biowin6 (MITI Non-Linear Model):   0.1110
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.3206
 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):  1.01E-005 Pa (7.61E-008 mm Hg)
  Log Koa (Koawin est  ): 16.458
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.296 
       Octanol/air (Koa) model:  7.05E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.914 
       Mackay model           :  0.959 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 141.2959 E-12 cm3/molecule-sec
      Half-Life =     0.076 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.908 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.937 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  76.24
      Log Koc:  1.882 

 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: -1.07 (estimated)

 Volatilization from Water:
    Henry LC:  7.26E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  1.18E+016  hours   (4.918E+014 days)
    Half-Life from Model Lake : 1.288E+017  hours   (5.365E+015 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       1.25e-010       1.82         1000       
   Water     39              360          1000       
   Soil      61              720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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