Lomustine

Lomustine
Clinical data
Trade names	Gleostine
Other names	1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
AHFS/Drugs.com	Monograph
MedlinePlus	a682207
Pregnancy; category	D;
Routes of; administration	Oral (capsules)
ATC code	L01AD02 (WHO) ;
Legal status
Legal status	US: WARNING; In general: ℞ (Prescription 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	233.695 g/mol 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 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^[3] 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.^[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.

Rebranding

In 2014, the drug was re-launched and rebranded as Gleostine, manufactured by NextSource Biotechnology.^[6]^[7]

References

^ "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.
^ 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. {{cite journal}}: |access-date= requires |url= (help)
^ "BC Cancer Agency Cancer Drug Manual. Lomustine (CCNU; CeeNU)" (PDF). Retrieved 15 July 2016.
^ Pizzo, PA; Poplack, DG, eds. (2006). Principles and Practice of Pediatric Oncology (5 ed.). Philadelphia: Lippincott Williams & Wilkins. p. 300. ISBN 9780781754927. {{cite book}}: |access-date= requires |url= (help)
^ "Gleostine (lomustine) Capsules, for Oral Use. Full Prescribing Information" (PDF). NextSource Biotechnology, LLC. Retrieved 15 July 2016.
^ "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.
^ "Gleostine (lomustine) Capsules — Healthcare Providers". NextSource Biotechnology. Retrieved 15 July 2016.

External links

CeeNu (lomustine) Capsules data sheet published by the FDA
Lomustine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
Diseases Database (DDB): 29525

This antineoplastic or immunomodulatory drug article is a stub. You can help Wikipedia by expanding it.

[FDA-AllBoxedWarnings-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): 125–31. doi:10.1007/bf00434350. PMID 3971475. {{cite journal}}: |access-date= requires |url= (help)

[Drug_Manual-3] "BC Cancer Agency Cancer Drug Manual. Lomustine (CCNU; CeeNU)" (PDF). Retrieved 15 July 2016.

[4] Pizzo, PA; Poplack, DG, eds. (2006). Principles and Practice of Pediatric Oncology (5 ed.). Philadelphia: Lippincott Williams & Wilkins. p. 300. ISBN 9780781754927. {{cite book}}: |access-date= requires |url= (help)

[PI-5] "Gleostine (lomustine) Capsules, for Oral Use. Full Prescribing Information" (PDF). NextSource Biotechnology, LLC. Retrieved 15 July 2016.

[6] "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.

[7] "Gleostine (lomustine) Capsules — Healthcare Providers". NextSource Biotechnology. Retrieved 15 July 2016.

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