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

6UXW23996M [DBID]
878 [DBID]
UNII:6UXW23996M [DBID]
AI3-26198 [DBID]
AIDS002314 [DBID]
AIDS-002314 [DBID]
B 518 [DBID]
BRN 0011744 [DBID]
C0768_SIAL [DBID]
C07888 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      white crystalline powder OU Chemical Safety Data (No longer updated) More details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

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 OU Chemical Safety Data (No longer updated) More details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

      Organic Compound; Organochloride; Amide; Ester; Drug; Antirheumatic Agent; Immunosuppressive Agent; Metabolite; Antineoplastic Agent, Alkylating; Synthetic Compound; Mutagen; Myeloablative Agonist Toxin, Toxin-Target Database T3D4688
      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LD50 137 mg kg-1, IPR-MUS LD50 159 mg kg-1, ORL-HAM LD50 763 mg kg-1, ITR-MUS LD50 200 mg kg-1 OU Chemical Safety Data (No longer updated) More details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. OU Chemical Safety Data (No longer updated) More details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, https://www.ebi.ac.uk/chebi/searchId.do?chebiId=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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