ContaminantDB: Lomustine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2014-09-11 02:05:33 UTC

Update Date

2026-03-26 21:11:04 UTC

Accession Number

CHEM003658

Identification

Common Name

Lomustine

Class

Small Molecule

Description

Lomustine is only found in individuals that have used or taken this drug. It is an alkylating agent of value against both hematologic malignancies and solid tumors. Lomustine is a highly lipophilic nitrosourea compound which undergoes hydrolysis in vivo to form reactive metabolites. These metabolites cause alkylation and cross-linking of DNA (at the O6 position of guanine-containing bases) and RNA, thus inducing cytotoxicity. Other biologic effects include inhibition of DNA synthesis and some cell cycle phase specificity. Nitrosureas generally lack cross-resistance with other alkylating agents. As lomustine is a nitrosurea, it may also inhibit several key processes such as carbamoylation and modification of cellular proteins.

Contaminant Sources

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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(2-Chloroethyl)-3-cyclohexyl-1-nitrosourea	ChEBI
1-(2-Chloroethyl)-3-cyclohexylnitrosourea	ChEBI
Belustine	ChEBI
CCNU	ChEBI
Cecenu	ChEBI
CeeNU	ChEBI
Chloroethylcyclohexylnitrosourea	ChEBI
CINU	ChEBI
Cyclohexyl chloroethyl nitrosourea	ChEBI
Lomustina	ChEBI
Lomustinum	ChEBI
N-(2-Chloroethyl)-n'-cyclohexyl-N-nitrosourea	ChEBI
Gleostine	Kegg
Bristol-myers squibb brand OF lomustine	HMDB
Rhône-poulenc rorer brand OF lomustine	HMDB
Medac brand OF lomustine	HMDB
Bristol myers squibb brand OF lomustine	HMDB
Rhône poulenc rorer brand OF lomustine	HMDB
Lomustine medac brand	HMDB

Chemical Formula

C₉H₁₆ClN₃O₂

Average Molecular Mass

233.695 g/mol

Monoisotopic Mass

233.093 g/mol

CAS Registry Number

13010-47-4

IUPAC Name

3-(2-chloroethyl)-1-cyclohexyl-3-nitrosourea

Traditional Name

lomustine

SMILES

ClCCN(N=O)C(=O)NC1CCCCC1

InChI Identifier

InChI=1S/C9H16ClN3O2/c10-6-7-13(12-15)9(14)11-8-4-2-1-3-5-8/h8H,1-7H2,(H,11,14)

InChI Key

GQYIWUVLTXOXAJ-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 homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

organochlorine compound (CHEBI:6520 )
N-nitrosoureas (CHEBI:6520 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
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	88 - 90°C
Boiling Point	Not Available
Solubility	111 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.76 g/L	ALOGPS
logP	2.62	ALOGPS
logP	2.16	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	13.3	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	4	ChemAxon
Refractivity	58.65 m³·mol⁻¹	ChemAxon
Polarizability	23.61 Å³	ChemAxon
Number of Rings	1	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	splash10-0059-8900000000-edefb2c60fb3a4723f1b	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	splash10-003r-9870000000-c1e5d9089d0ca3ebe990	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004j-9600000000-553a8bea32ca95f8b8c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-237df2753e3c79610270	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05aj-4940000000-52228cb236f776094d55	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9520000000-f52d4c064b87d135bcab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9100000000-c986da9a3b5f2025b30c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-9410000000-3c91b816a1fd60d9fb41	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-9100000000-e9795a3320548e7e0520	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-13ca0d883f27e08e4efe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-3190000000-21d4dc32f394af73cd0d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-99ed100e7c6291a96d1b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-7fe5321df11e6429faf4	Spectrum

Toxicity Profile

Route of Exposure

Well and rapidly absorbed from the gastrointestinal tract.

Mechanism of Toxicity

Lomustine is a highly lipophilic nitrosourea compound which undergoes hydrolysis in vivo to form reactive metabolites. These metabolites cause alkylation and cross-linking of DNA (at the O6 position of guanine-containing bases) and RNA, thus inducing cytotoxicity. Other biologic effects include inhibition of DNA synthesis and some cell cycle phase specificity. Nitrosureas generally lack cross-resistance with other alkylating agents. As lomustine is a nitrosurea, it may also inhibit several key processes such as carbamoylation and modification of cellular proteins.

Metabolism

Hepatic. Rapid and complete, with active metabolites. Route of Elimination: Following oral administration of radioactive CeeNU at doses ranging from 30 mg/m2 to 100 mg/m2, about half of the radioactivity given was excreted in the urine in the form of degradation products within 24 hours. Half Life: Approximately 94 minutes, however the metabolites have a serum half-life of 16 to 48 hours.

Toxicity Values

Oral, rat: LD₅₀ = 70 mg/kg. Pulmonary toxicity has been reported at cumulative doses usually greater than 1,100 mg/m2. There is one report of pulmonary toxicity at a cumulative dose of only 600 mg. The onset of toxicity has varied from 6 months after initiation of therapy, to as late as 15 years after.

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2A, probably carcinogenic to humans. (1)

Uses/Sources

For the treatment of primary and metastatic brain tumors as a component of combination chemotherapy in addition to appropriate surgical and/or radiotherapeutic procedures. Also used in combination with other agents as secondary therapy for the treatment of refractory or relapsed Hodgkin's disease.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID