CHEBI:6520 - lomustine

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ChEBI Name lomustine
ChEBI ID CHEBI:6520
Definition An N-nitrosourea that is urea in which one of the nitrogens is substituted by a 2-chloroethyl group and by a nitroso group, while the other nitrogen is substituted by a cyclohexyl group. An alkylating antineoplastic agent, it is used in the treatment of brain tumours, lung cancer, malignant melanoma and other solid tumours.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB5123021, eMolecules:734270, Selleckchem:Lomustine(CeeNU), ZINC000003831006
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Lomustine (INN; abbreviated as CCNU; original brand name CeeNU, now marketed as Gleostine) is an alkylating nitrosourea compound used in chemotherapy. It is closely related to semustine and is in the same family as streptozotocin. It is a highly lipid-soluble drug, thus it crosses the blood–brain barrier. This property makes it ideal for treating brain tumors, which is its primary use, although it is also used to treat Hodgkin lymphoma as a second-line option. It has also been used in veterinary practice as a treatment for cancers in cats and dogs. Lomustine is a bifunctional alkylating agent, alkylates both DNA and RNA, has the ability to created interstrand cross-links (ICLs) in DNA. As with other nitrosoureas, it may also inhibit several key enzymatic processes by carbamoylation of amino acids in proteins. Lomustine is cell-cycle nonspecific.
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Formula C9H16ClN3O2
Net Charge 0
Average Mass 233.69500
Monoisotopic Mass 233.09310
InChI 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)
InChIKey GQYIWUVLTXOXAJ-UHFFFAOYSA-N
SMILES ClCCN(N=O)C(=O)NC1CCCCC1
Roles Classification
Biological Role(s): alkylating agent
Highly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing lomustine (CHEBI:6520) has role alkylating agent (CHEBI:22333)
lomustine (CHEBI:6520) has role antineoplastic agent (CHEBI:35610)
lomustine (CHEBI:6520) is a N-nitrosoureas (CHEBI:76551)
lomustine (CHEBI:6520) is a organochlorine compound (CHEBI:36683)
IUPAC Name
1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
INNs Sources
lomustina WHO MedNet
lomustine KEGG DRUG
lomustine WHO MedNet
lomustinum WHO MedNet
Synonyms Sources
1-(2-Chloroethyl)-3-cyclohexyl-1-nitrosourea KEGG COMPOUND
1-(2-chloroethyl)-3-cyclohexylnitrosourea ChemIDplus
CCNU ChemIDplus
chloroethylcyclohexylnitrosourea ChemIDplus
CINU ChemIDplus
cyclohexyl chloroethyl nitrosourea ChemIDplus
N-(2-chloroethyl)-N'-cyclohexyl-N-nitrosourea ChEBI
N-(2-chloroethyl)-N'-cyclohexyl-N-nitrosourea ChemIDplus
Brand Names Sources
Belustine ChemIDplus
Cecenu ChemIDplus
CeeNU KEGG DRUG
Manual Xrefs Databases
1596 DrugCentral
C07079 KEGG COMPOUND
D00363 KEGG DRUG
DB01206 DrugBank
HMDB0015337 HMDB
Lomustine Wikipedia
View more database links
Registry Numbers Types Sources
13010-47-4 CAS Registry Number KEGG COMPOUND
13010-47-4 CAS Registry Number ChemIDplus
2125058 Reaxys Registry Number Reaxys
Citations Waiting for Citations
Last Modified
22 February 2017