ChemSpider 2D Image | Carmustine | C5H9Cl2N3O2


  • Molecular FormulaC5H9Cl2N3O2
  • Average mass214.050 Da
  • Monoisotopic mass213.007187 Da
  • ChemSpider ID2480

More details:

Featured data source

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

1,3-Bis(2-chlorethyl)-1-nitrosoharnstoff [German] [ACD/IUPAC Name]
1,3-Bis(2-chloroethyl)-1-nitrosourea [ACD/IUPAC Name]
1,3-Bis(2-chloroéthyl)-1-nitrosourée [French] [ACD/IUPAC Name]
154-93-8 [RN]
205-838-2 [EINECS]
Acide N,N'-bis(2-chloroéthyl)-N-nitrosocarbamimidique [French] [ACD/IUPAC Name]
Carmustina [Spanish] [INN]

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

2959 [DBID]
U68WG3173Y [DBID]
YS2625000 [DBID]
AI3-52216 [DBID]
AIDS000666 [DBID]
AIDS-000666 [DBID]
BCNU, N,N'-bis(2-chloroethyl)-N-nitrosourea, NSC-409962, becenun, bicnu, [DBID]
BRN 2049744 [DBID]
  • Spectroscopy
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Toxicity:

      Organic Compound; Organochloride; Amine; Drug; Metabolite; Antineoplastic Agent, Alkylating; Synthetic Compound Toxin, Toxin-Target Database T3D4681
    • Safety:

      45-46-60-61-28 LKT Labs [C0173]
      Danger Biosynth W-108025
      GHS06; GHS08 Biosynth W-108025
      H300 H350 H360 LKT Labs [C0173]
      H300; H350; H360 Biosynth W-108025
      IRRITANT Matrix Scientific 094162
      L01AD01 Wikidata Q415869
      P201; P264; P301+P310; P308+P313 Biosynth W-108025
      T+ LKT Labs [C0173]
      UN 2811 6.1/PG 2 LKT Labs [C0173]
    • Chemical Class:

      A member of the class of <element>N</element>-nitrosoureas that is 1,3-bis(2-chloroethyl)urea in which one of the nitrogens is substituted by a nitroso group. ChEBI CHEBI:3423
    • Compound Source:

      synthetic Microsource [01503110]
    • Bio Activity:

      Antineoplastic agent; Zerenex Molecular [ZBioX-0111]
      Carmustine is a cell-cycle phase nonspecific alkylating antineoplastic agent. MedChem Express
      Carmustine is a cell-cycle phase nonspecific alkylating antineoplastic agent.; Target: DNA alkylator/crosslinker; Carmustine causes cross-links in DNA and RNA, leading to the inhibition of DNA synthesis, RNA production and RNA translation (protein synthesis). MedChem Express HY-13585
      Carmustine is a cell-cycle phase nonspecific alkylating antineoplastic agent.;Target: DNA alkylator/crosslinkerCarmustine causes cross-links in DNA and RNA, leading to the inhibition of DNA synthesis, RNA production and RNA translation (protein synthesis). Carmustine also binds to and modifies (carbamoylates) glutathione reductase. This leads to cell death. Carmustine (1,3-bis (2-chloroethyl)-1-nitrosourea) is a nitrosourea alkylating agent that exerts its antitumor effect by akylating DNA and RNA. The development of carmustine wafers (Gliadel((R)) Wafer) as a method for controlled released delivery of carmustine from biodegradable polymer wafers enhances the therapeutic ratio by fully containing the drug within the confines of the brain tumor environment while minimizing systemic toxicities [1, 2]. MedChem Express HY-13585
      Cell Cycle/DNA Damage MedChem Express HY-13585
      Cell Cycle/DNA Damage; MedChem Express HY-13585
      DNA alkylator/crosslinker MedChem Express HY-13585
  • Gas Chromatography

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

Density: 1.5±0.1 g/cm3
Boiling Point: 309.6±52.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 63.8±6.0 kJ/mol
Flash Point: 141.0±30.7 °C
Index of Refraction: 1.549
Molar Refractivity: 46.6±0.5 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 1.12
ACD/LogD (pH 5.5): 1.00
ACD/BCF (pH 5.5): 3.40
ACD/KOC (pH 5.5): 83.61
ACD/LogD (pH 7.4): 0.97
ACD/BCF (pH 7.4): 3.13
ACD/KOC (pH 7.4): 76.95
Polar Surface Area: 65 Å2
Polarizability: 18.5±0.5 10-24cm3
Surface Tension: 50.4±7.0 dyne/cm
Molar Volume: 146.4±7.0 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) =  1.44
    Log Kow (Exper. database match) =  1.53
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  333.07  (Adapted Stein & Brown method)
    Melting Pt (deg C):  120.99  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.000293  (Modified Grain method)
    MP  (exp database):  31 deg C
    Subcooled liquid VP: 0.000331 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):  1826
       log Kow used: 1.53 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  4000 mg/L (25 deg C)
        Exper. Ref:  MERCK (1989)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  7857.7 mg/L
    Wat Sol (Exper. database match) =  4000.00
       Exper. Ref:  MERCK (1989)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.76E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.519E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.53  (exp database)
  Log Kaw used:  -8.711  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.241
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4229
   Biowin2 (Non-Linear Model)     :   0.0233
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3798  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3377  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2752
   Biowin6 (MITI Non-Linear Model):   0.0386
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.9107
 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):  0.0441 Pa (0.000331 mm Hg)
  Log Koa (Koawin est  ): 10.241
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6.8E-005 
       Octanol/air (Koa) model:  0.00428 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00245 
       Mackay model           :  0.00541 
       Octanol/air (Koa) model:  0.255 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   3.6303 E-12 cm3/molecule-sec
      Half-Life =     2.946 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    35.356 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.00393 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  326.5
      Log Koc:  2.514 

 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 = 0.478 (BCF = 3.007)
       log Kow used: 1.53 (expkow database)

 Volatilization from Water:
    Henry LC:  4.76E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:   1.8E+007  hours   (7.498E+005 days)
    Half-Life from Model Lake : 1.963E+008  hours   (8.18E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               1.98  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.89  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       0.000541        70.7         1000       
   Water     32.3            900          1000       
   Soil      67.6            1.8e+003     1000       
   Sediment  0.0831          8.1e+003     0          
     Persistence Time: 1.2e+003 hr


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