Lomustine

Lomustine

Clinical data
Trade names	Gleostine
AHFS/Drugs.com	Monograph
MedlinePlus	a682207
Pregnancy category	D
Routes of administration	Oral (capsules)
ATC code	L01AD02 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	~100%
Protein binding	50%
Metabolism	Liver
Metabolites	Monoxydroxylated metabolites, trans-4-hydroxy-CCNU, cis-4-hydroxy-CCNU
Biological half-life	16–48 hours (metabolites)
Identifiers
IUPAC name N-(2-chloroethyl)-N'-cyclohexyl-N-nitrosourea
Synonyms	1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
CAS Number	13010-47-4 Y
PubChem (CID)	3950
IUPHAR/BPS	7214
DrugBank	DB01206 Y
ChemSpider	3813 Y
UNII	7BRF0Z81KG Y
KEGG	D00363 Y
ChEBI	CHEBI:6520 N
ChEMBL	CHEMBL514 Y
ECHA InfoCard	100.032.585
Chemical and physical data
Formula	C9H16ClN3O2
Molar mass	233.695 g/mol
3D model (Jmol)	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) Y Key:GQYIWUVLTXOXAJ-UHFFFAOYSA-N Y
NY (what is this?)

Lomustine (INN), abbreviated CCNU (original brand name (formerly available) is 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 . It is a highly lipid-soluble drug and thus crosses the blood-brain barrier. This property makes it ideal for treating brain tumors, which is its primary use. Lomustine has a long time to nadir (the time when white blood cells reach their lowest number).

Unlike carmustine, lomustine is administered orally. It is a monofunctional alkylating agent, alkylates both DNA and RNA, has the ability to cross-link 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.

In 2014, the drug was re-launched and rebranded as Gleostine, manufactured by NextSource Biotechnology.