ContaminantDB: Carmustine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2014-09-11 02:04:43 UTC

Update Date

2026-05-14 16:25:01 UTC

Accession Number

CHEM003639

Identification

Common Name

Carmustine

Class

Small Molecule

Description

Carmustine 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
Human Neurotoxin
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
BCNU	ChEBI
Bicnu	ChEBI
Bischloroethyl nitrosourea	ChEBI
Carmustina	ChEBI
Carmustinum	ChEBI
Gliadel	ChEBI
N,N'-bis(2-chloroethyl)-N-nitrosourea	ChEBI
Bischlorethylnitrosourea	HMDB
Bischlorethylnitrosurea	HMDB
Carmustin	HMDB
FIVB	HMDB
Nitrumon	HMDB
1,3-Bis(2-chloroethyl)-1-nitrosourea	HMDB

Chemical Formula

C₅H₉Cl₂N₃O₂

Average Molecular Mass

214.050 g/mol

Monoisotopic Mass

213.007 g/mol

CAS Registry Number

154-93-8

IUPAC Name

1,3-bis(2-chloroethyl)-1-nitrosourea

Traditional Name

carmustine

SMILES

ClCCNC(=O)N(CCCl)N=O

InChI Identifier

InChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)

InChI Key

DLGOEMSEDOSKAD-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic carbonic acids and derivatives

Sub Class

Ureas

Direct Parent

Nitrosoureas

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 Framework

Aliphatic acyclic compounds

External Descriptors

organochlorine compound (CHEBI:3423 )
N-nitrosoureas (CHEBI:3423 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	31°C
Boiling Point	Not Available
Solubility	4000 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	1.53 g/L	ALOGPS
logP	1.24	ALOGPS
logP	1.02	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	11.96	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	61.77 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	46.98 m³·mol⁻¹	ChemAxon
Polarizability	18.8 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bu0-6900000000-7ee333c26479b9275253	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06vi-9630000000-1b262631b4a720cd9eba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9500000000-fbebb9877cfb22d2c3d8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03fr-9000000000-86de321ebee3984d7705	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-116u-4930000000-a2c48761c56e3640e06b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004l-6900000000-fc62a96dc02889b5a3b7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-9200000000-d116bdf5580083ca15c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-4390000000-26b54291487efd0acb6f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9400000000-52b9e7457ec89c9907c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-d239cf72a61995f936f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-4390000000-a11de64a3d45d4733ab2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9200000000-a9b03f4595d1bb5cb7d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9200000000-14857476fd37bc517cbb	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Carmustine 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.

Metabolism

Hepatic 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 Values

The oral LD₅₀s in rat and mouse are 20 mg/kg and 45 mg/kg, respectively.

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2A, probably carcinogenic to humans. (1)

Uses/Sources

For the treatment of brain tumors, multiple myeloma, Hodgkin's disease and Non-Hodgkin's lymphomas.

Minimum Risk Level

Not Available

Health Effects

Not Available