ChemSpider 2D Image | Cyclophosphamide | C7H15Cl2N2O2P

Cyclophosphamide

  • Molecular FormulaC7H15Cl2N2O2P
  • Average mass261.086 Da
  • Monoisotopic mass260.024811 Da
  • ChemSpider ID2804

More details:






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

Cyclophosphamide [INN] [USP] [Wiki]
(±)-Cyclophosphamide
(±)-Cyclophosphamide
(RS)-Cyclophosphamide
2-(bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
2-(bis(2-Chloroethyl)-amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazophosphorine 2-oxide
2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazophosphorine 2-Oxide
2-[Bis(2-chloroethylamino)]-tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AI3-26198 [DBID]
AIDS002314 [DBID]
AIDS-002314 [DBID]
B 518 [DBID]
BRN 0011744 [DBID]
C0768_SIAL [DBID]
C07888 [DBID]
cb 4564 [DBID]
CB-4564 [DBID]
CCRIS 188 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      white crystalline powder Oxford University Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable, but light sensitive. Incompatible with oxidizing agents. Oxford University Chemical Safety Data (No longer updated) More details
    • Toxicity:

      ORL-MUS LD50 137 mg kg-1, IPR-MUS LD50 159 mg kg-1, ORL-HAM LD50 763 mg kg-1, ITR-MUS LD50 200 mg kg-1 Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      45-46-61-25 Alfa Aesar L11508
      53-20-36-45-60 Alfa Aesar L11508
      DANGER: POISON, cancer risk, causes liver damage Alfa Aesar L11508
      L01AA01 Wikidata Q408524
      Safety glasses, gloves. Do not breathe dust. Oxford University Chemical Safety Data (No longer updated) More details
      TBC SynQuest 8H79-5-00
      TOXIC Alfa Aesar L11508
    • Chemical Class:

      A phosphorodiamide that is 1,3,2-oxazaphosphinan-2-amine 2-oxide substituted by two 2-chloroethyl groups at the amino nitrogen atom. ChEBI CHEBI:4027
    • Bio Activity:

      Alkylating agent; chemotherapeutic Tocris Bioscience 4091
      Apoptosis Tocris Bioscience 4091
      Apoptosis Inducers Tocris Bioscience 4091
      Cell Biology Tocris Bioscience 4091
      Cell Cycle/DNA Damage MedChem Express HY-17420
      Cell Cycle/DNA Damage; MedChem Express HY-17420
      Cyclophosphamide is a synthetic alkylating agent chemically related to the nitrogen mustards with antineoplastic and immunosuppressive activities. MedChem Express http://www.medchemexpress.com/mevastatin.html, HY-17420
      DNA alkylator/crosslinker MedChem Express HY-17420
      Nitrogen mustard alkylating agent and prodrug. Phosphoramide mustard (active metabolite) forms DNA cross-links leading to cell death. Inhibits aldehyde dehydrogenase 1 (ALDH1) through its degradation product acrolein. Chemotherapeutic for the treatment of breast cancer; regulates Bax and Bcl-2 expression when administered with etoposide (Cat. No. 1226) in breast cancer cell lines. Tocris Bioscience 4091
      Nitrogen mustard alkylating agent and prodrug. Phosphoramide mustard (active metabolite) forms DNA cross-links leading to cell death. Inhibits aldehyde dehydrogenase 1 (ALDH1) through its degradation product acrolein. Chemotherapeutic for the treatment of breast cancer; regulates Bax and Bcl-2 expression when administered with etoposide (Cat. No. 1226) in breast cancer cell lines. Tocris Bioscience 4091

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

Density: 1.3±0.1 g/cm3
Boiling Point: 336.1±52.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.7 mmHg at 25°C
Enthalpy of Vaporization: 57.9±3.0 kJ/mol
Flash Point: 157.1±30.7 °C
Index of Refraction: 1.506
Molar Refractivity: 58.1±0.4 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 0.23
ACD/LogD (pH 5.5): 0.52
ACD/BCF (pH 5.5): 1.48
ACD/KOC (pH 5.5): 45.93
ACD/LogD (pH 7.4): 0.53
ACD/BCF (pH 7.4): 1.48
ACD/KOC (pH 7.4): 46.03
Polar Surface Area: 51 Å2
Polarizability: 23.0±0.5 10-24cm3
Surface Tension: 44.3±5.0 dyne/cm
Molar Volume: 195.7±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) =  0.97
    Log Kow (Exper. database match) =  0.63
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  359.82  (Adapted Stein & Brown method)
    Melting Pt (deg C):  85.72  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.4E-005  (Modified Grain method)
    MP  (exp database):  51.5 deg C
    Subcooled liquid VP: 7.71E-005 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):  5943
       log Kow used: 0.63 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  4e+004 mg/L (20 deg C)
        Exper. Ref:  IARC (1975)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  57921 mg/L
    Wat Sol (Exper. database match) =  40000.00
       Exper. Ref:  IARC (1975)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters
       Esters (phosphate)

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.36E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.543E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.63  (exp database)
  Log Kaw used:  -9.255  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.885
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4005
   Biowin2 (Non-Linear Model)     :   0.0121
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2758  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.2698  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1944
   Biowin6 (MITI Non-Linear Model):   0.0206
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5507
 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):  0.0103 Pa (7.71E-005 mm Hg)
  Log Koa (Koawin est  ): 9.885
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000292 
       Octanol/air (Koa) model:  0.00188 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0104 
       Mackay model           :  0.0228 
       Octanol/air (Koa) model:  0.131 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  70.2751 E-12 cm3/molecule-sec
      Half-Life =     0.152 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.826 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.0166 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  317.7
      Log Koc:  2.502 

 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: 0.63 (expkow database)

 Volatilization from Water:
    Henry LC:  1.36E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.956E+007  hours   (2.898E+006 days)
    Half-Life from Model Lake : 7.589E+008  hours   (3.162E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       0.000185        3.65         1000       
   Water     43.7            900          1000       
   Soil      56.2            1.8e+003     1000       
   Sediment  0.0875          8.1e+003     0          
     Persistence Time: 1.01e+003 hr




                    

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