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Lomustine

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Dec 12, 2021

Lomustine (INN); abbreviated as CCNU; original brand name CeeNU, now marketed as Gleostine) is an alkylatingnitrosourea 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] 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.[3] Lomustine has a long time to nadir (the time when white blood cells reach their lowest number).

Lomustine
Clinical data
Trade names Gleostine
Other names 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
AHFS/Drugs.com Monograph
MedlinePlus a682207
Pregnancy
category
  • AU: D
Routes of
administration
Oral (capsules)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability ~100%
Protein binding 50%
Metabolism Liver
Metabolites Monoxydroxylated metabolites, trans-4-hydroxy-CCNU, cis-4-hydroxy-CCNU[1]
Elimination half-life 16–48 hours (metabolites)
Identifiers
  • N-(2-Chloroethyl)-N’-cyclohexyl-N-nitrosourea
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard 100.032.585
Chemical and physical data
Formula C9H16ClN3O2
Molar mass 233.70 g·mol−1
3D model (JSmol)
Melting point 90 °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) Y
  • Key:GQYIWUVLTXOXAJ-UHFFFAOYSA-N Y

 NY (what is this?)  (verify)

Unlike carmustine, lomustine is administered orally. It is a bifunctional alkylating agent, alkylates both DNA and RNA, has the ability to created interstrand cross-links (ICLs) in DNA.[4] As with other nitrosoureas, it may also inhibit several key enzymatic processes by carbamoylation of amino acids in proteins.[5] Lomustine is cell-cycle nonspecific.

It has also been used in veterinary practice as a treatment for mast cell tumors in dogs.[6]

. . . Lomustine . . .

In the U.S., the patent for lomustine has expired, but only one company manufactures it. In 2013, Bristol-Myers Squibb Co. sold its CeeNU brand of lomustine to CordenPharma, a subsidiary of International Chemical Investors S.E., which markets it as Gleostine through NextSource Biotechnology. In 2013, BMS charged $50 a capsule. In 2018, NextSource charged $768 a capsule. Some doctors said the price increase made it unaffordable, and one doctor called it “price gouging.”[7][8][9]

  1. Lee FY, Workman P, Roberts JT, Bleehen NM (1985). “Clinical pharmacokinetics of oral CCNU (lomustine)”. Cancer Chemotherapy and Pharmacology. 14 (2): 125–31. doi:10.1007/bf00434350. PMID 3971475. S2CID 29619378.
  2. “BC Cancer Agency Cancer Drug Manual. Lomustine (CCNU; CeeNU)”(PDF). Retrieved 15 July 2016.
  3. “PRODUCT INFORMATION CeeNU®(lomustine)”(PDF). TGA eBusiness Services. Bristol-Myers Squibb Australia Pty Ltd. 30 September 2015. Retrieved 23 April 2018.
  4. Pizzo PA, Poplack DG, eds. (2006). Principles and Practice of Pediatric Oncology (5th ed.). Philadelphia: Lippincott Williams & Wilkins. p. 300. ISBN 9780781754927.
  5. “Gleostine (lomustine) Capsules, for Oral Use. Full Prescribing Information”(PDF). NextSource Biotechnology, LLC. Retrieved 15 July 2016.
  6. Weiss DJ, Wardrop KJ, Weiss D (2010). Schalm’s Veterinary Hematology (6 ed.). John Wiley & Sons, Incorporate d. p. 487. ISBN 978-0-8138-0896-3.
  7. Cancer Drug Price Rises 1400% With No Generic to Challenge It, Peter Loftus, The Wall Street Journal, 12/26/2017 [FREE]
  8. “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.
  9. “Gleostine (lomustine) Capsules — Healthcare Providers”. NextSource Biotechnology. Retrieved 15 July 2016.

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. . . Lomustine . . .