Lomustine

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Lomustine
Lomustine.svg
Lomustine ball-and-stick model.png
Systematic (IUPAC) name
N-(2-chloroethyl)-N'-cyclohexyl-N-nitrosourea
Clinical data
Trade names Gleostine
AHFS/Drugs.com Monograph
MedlinePlus a682207
Pregnancy
category
  • D
Routes of
administration
Oral (capsules)
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[1]
Biological half-life 16–48 hours (metabolites)
Identifiers
CAS Number 13010-47-4 YesY
ATC code L01AD02 (WHO)
PubChem CID 3950
IUPHAR/BPS 7214
DrugBank DB01206 YesY
ChemSpider 3813 YesY
UNII 7BRF0Z81KG YesY
KEGG D00363 YesY
ChEBI CHEBI:6520 N
ChEMBL CHEMBL514 YesY
Synonyms 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
Chemical data
Formula C9H16ClN3O2
Molar mass 233.695 g/mol
Physical data
Melting point 90 °C (194 °F)
 NYesY (what is this?)  (verify)

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 streptozotocin. It is a highly lipid-soluble drug[2] 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.[3] As with other nitrosoureas, it may also inhibit several key enzymatic processes by carbamoylation of amino acids in proteins.[4] Lomustine is cell-cycle nonspecific.

Rebranding[edit]

In 2014, the drug was re-launched and rebranded as Gleostine, manufactured by NextSource Biotechnology.[5][6]

References[edit]

  1. ^ Lee, FY; Workman, P; Roberts, JT; Bleehen, NM (1985). "Clinical Pharmacokinetics of Oral CCNU (lomustine)". Cancer Chemotherapy and Pharmacology 14 (2): 125–31. PMID 3971475. 
  2. ^ "BC Cancer Agency Cancer Drug Manual. Lomustine (CCNU; CeeNU)" (PDF). Retrieved 15 July 2016. 
  3. ^ Pizzo, PA; Poplack, DG, eds. (2006). Principles and Practice of Pediatric Oncology (5 ed.). Philadelphia: Lippincott Williams & Wilkins. p. 300. ISBN 9780781754927. 
  4. ^ "Gleostine (lomustine) Capsules, for Oral Use. Full Prescribing Information" (PDF). NextSource Biotechnology, LLC. Retrieved 15 July 2016. 
  5. ^ "NextSource Biotechnology Gains FDA Approval for Use of Tradename Gleostine (lomustine), an Anti-Cancer Chemotherapy Agent". www.prnewswire.com. NextSource Biotechnology. Retrieved 15 July 2016. 
  6. ^ "Gleostine (lomustine) Capsules — Healthcare Providers". NextSource Biotechnology. Retrieved 15 July 2016. 

External links[edit]