Lomustine

Lomustine
Clinical data
Trade namesGleostine, CCNU, CeeNu, CuuNu
Other names1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
AHFS/Drugs.comMonograph
MedlinePlusa682207
Routes of
administration		Oral (capsules)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability~100%
Protein binding50%
MetabolismLiver
MetabolitesMonoxydroxylated metabolites, trans-4-hydroxy-CCNU, cis-4-hydroxy-CCNU[2]
Elimination half-life16–48 hours (metabolites)
Identifiers
  • N-(2-Chloroethyl)-N'-cyclohexyl-N-nitrosourea
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.032.585 Edit this at Wikidata
Chemical and physical data
FormulaC9H16ClN3O2
Molar mass233.70 g·mol−1
3D model (JSmol)
Melting point90 °C (194 °F)
  • O=C(NC1CCCCC1)N(N=O)CCCl
  • 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) checkY
  • Key:GQYIWUVLTXOXAJ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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,[3] 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.[4] It has also been used in veterinary practice as a treatment for cancers in cats and dogs.[5]

Lomustine is a bifunctional alkylating agent, alkylates both DNA and RNA, has the ability to created interstrand cross-links (ICLs) in DNA.[6] As with other nitrosoureas, it may also inhibit several key enzymatic processes by carbamoylation of amino acids in proteins.[7] Lomustine is cell-cycle nonspecific.

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ Lee FY, Workman P, Roberts JT, Bleehen NM (1985). "Clinical pharmacokinetics of oral CCNU (lomustine)". Cancer Chemotherapy and Pharmacology. 14 (2): 125–131. doi:10.1007/bf00434350. PMID 3971475. S2CID 29619378.
  3. ^ "BC Cancer Agency Cancer Drug Manual. Lomustine (CCNU; CeeNU)" (PDF). Retrieved 15 July 2016.
  4. ^ "PRODUCT INFORMATION CeeNU(lomustine)" (PDF). TGA eBusiness Services. Bristol-Myers Squibb Australia Pty Ltd. 30 September 2015. Retrieved 23 April 2018.
  5. ^ Cite error: The named reference Vca was invoked but never defined (see the help page).
  6. ^ Pizzo PA, Poplack DG, eds. (2006). Principles and Practice of Pediatric Oncology (5th ed.). Philadelphia: Lippincott Williams & Wilkins. p. 300. ISBN 9780781754927.
  7. ^ "Gleostine (lomustine) Capsules, for Oral Use. Full Prescribing Information" (PDF). NextSource Biotechnology, LLC. Retrieved 15 July 2016.