Carmustine (CHEM003639)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2014-09-11 02:04:43 UTC
Update Date2016-11-09 01:09:11 UTC
Accession NumberCHEM003639
Identification
Common NameCarmustine
ClassSmall Molecule
DescriptionCarmustine is a cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 2A
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Antineoplastic Agent, Alkylating
  • Drug
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
BCNUChEBI
BicnuChEBI
Bischloroethyl nitrosoureaChEBI
CarmustinaChEBI
CarmustinumChEBI
GliadelChEBI
N,N'-bis(2-chloroethyl)-N-nitrosoureaChEBI
BischlorethylnitrosoureaHMDB
BischlorethylnitrosureaHMDB
CarmustinHMDB
FIVBHMDB
NitrumonHMDB
1,3-Bis(2-chloroethyl)-1-nitrosoureaHMDB
Chemical FormulaC5H9Cl2N3O2
Average Molecular Mass214.050 g/mol
Monoisotopic Mass213.007 g/mol
CAS Registry Number154-93-8
IUPAC Name1,3-bis(2-chloroethyl)-3-nitrosourea
Traditional Namecarmustine
SMILESClCCNC(=O)N(CCCl)N=O
InChI IdentifierInChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)
InChI KeyDLGOEMSEDOSKAD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitrosoureas. Nitrosoureas are compounds containing a nitro group and an urea group N-N linked together, with the general structure R1N(R2)C(=O)N(R3)N=O.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic carbonic acids and derivatives
Sub ClassUreas
Direct ParentNitrosoureas
Alternative Parents
Substituents
  • Nitrosourea
  • Semicarbazide
  • Nitrosamide
  • Organic n-nitroso compound
  • Organic nitroso compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alkyl chloride
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point31°C
Boiling PointNot Available
Solubility4000 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility1.53 g/LALOGPS
logP1.24ALOGPS
logP1.02ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)11.96ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area61.77 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity46.98 m³·mol⁻¹ChemAxon
Polarizability18.8 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bu0-6900000000-7ee333c26479b9275253Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06vi-9630000000-1b262631b4a720cd9ebaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9500000000-fbebb9877cfb22d2c3d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-9000000000-86de321ebee3984d7705Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-116u-4930000000-a2c48761c56e3640e06bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-6900000000-fc62a96dc02889b5a3b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9200000000-d116bdf5580083ca15c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4390000000-26b54291487efd0acb6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9400000000-52b9e7457ec89c9907c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-d239cf72a61995f936f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4390000000-a11de64a3d45d4733ab2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9200000000-a9b03f4595d1bb5cb7d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9200000000-14857476fd37bc517cbbSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityCarmustine 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.
MetabolismHepatic and rapid with active metabolites. Metabolites may persist in the plasma for several days. Route of Elimination: Approximately 60% to 70% of a total dose is excreted in the urine in 96 hours and about 10% as respiratory CO2. Half Life: 15-30 minutes
Toxicity ValuesThe oral LD50s in rat and mouse are 20 mg/kg and 45 mg/kg, respectively.
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2A, probably carcinogenic to humans. (1)
Uses/SourcesFor the treatment of brain tumors, multiple myeloma, Hodgkin's disease and Non-Hodgkin's lymphomas.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00262
HMDB IDHMDB0014407
FooDB IDFDB012974
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCarmustine
Chemspider ID2480
ChEBI ID3423
PubChem Compound ID2578
Kegg Compound IDC06873
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General ReferencesNot Available