Lomustine

Lomustine
Clinical data
Trade names	Gleostine, CCNU, CeeNu, CuuNu
Other names	1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
AHFS/Drugs.com	Monograph
MedlinePlus	a682207
Routes of; administration	Oral (capsules)
ATC code	L01AD02 (WHO) ;
Legal status
Legal status	CA: ℞-only; UK: POM (Prescription only); US: WARNINGRx-only;
Pharmacokinetic data
Bioavailability	~100%
Protein binding	50%
Metabolism	Liver
Metabolites	Monoxydroxylated metabolites, trans-4-hydroxy-CCNU, cis-4-hydroxy-CCNU
Elimination half-life	16–48 hours (metabolites)
Identifiers
	IUPAC name N-(2-Chloroethyl)-N'-cyclohexyl-N-nitrosourea;
CAS Number	13010-47-4 ;
PubChem CID	3950;
IUPHAR/BPS	7214;
DrugBank	DB01206 ;
ChemSpider	3813 ;
UNII	7BRF0Z81KG;
KEGG	D00363 ;
ChEBI	CHEBI:6520 ;
ChEMBL	ChEMBL514 ;
CompTox Dashboard (EPA)	DTXSID2023222 ;
ECHA InfoCard	100.032.585
Chemical and physical data
Formula	C9H16ClN3O2
Molar mass	233.70 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	90 °C (194 °F)
	SMILES O=C(NC1CCCCC1)N(N=O)CCCl;
	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) ; Key:GQYIWUVLTXOXAJ-UHFFFAOYSA-N ;
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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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