Structure via PubChem · Public domain (PubChem)
lomustine
Sign in to saveAlso known as CCNU, CeeNU®, N-(2-chloroethyl)-N'-cyclohexyl-N-nitrosourea, 1-(2-chloroethyl)-3-cyclohexylnitrosourea, CINU, cyclohexyl chloroethyl nitrosourea, chloroethylcyclohexylnitrosourea, 1-(2-Chloroethyl)-3-cyclohexyl-1-nitrosourea
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, 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. It has also been used in veterinary practice as a treatment for cancers in cats and dogs.
Key facts
- Drug.N
- 3
- Drug.O
- 2
- Drug.H
- 16
- Drug.Cl
- 1
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 462093427
- Drug.IUPAC_name
- N-(2-Chloroethyl)-N'-cyclohexyl-N-nitrosourea
- Drug.image
- Lomustine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.image2
- Lomustine ball-and-stick model.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 175
- Drug.tradename
- Gleostine, CCNU, CeeNu, CuuNu
- Drug.MedlinePlus
- a682207
- Drug.pregnancy_US
- D
- Drug.legal_CA
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C9H16ClN3O2
- Molecular weight
- 233.69 g/mol
- IUPAC name
- 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
- SMILES
- C1CCC(CC1)NC(=O)N(CCCl)N=O
- InChIKey
- GQYIWUVLTXOXAJ-UHFFFAOYSA-N
- XLogP
- 2.8
- Polar surface area
- 61.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
3,011 papers- Lomustine and Bevacizumab in Progressive Glioblastoma.The New England journal of medicine · 2017
- Lomustine, methotrexate and cytarabine chemotherapy as a rescue treatment for feline lymphoma.Journal of feline medicine and surgery · 2021
- Regorafenib compared with lomustine in patients with relapsed glioblastoma (REGOMA): a multicentre, open-label, randomised, controlled, phase 2 trial.The Lancet. Oncology · 2019
- How did lomustine become standard of care in recurrent glioblastoma?Cancer treatment reviews · 2020
- Single-agent bevacizumab or lomustine versus a combination of bevacizumab plus lomustine in patients with recurrent glioblastoma (BELOB trial): a randomised controlled phase 2 trial.The Lancet. Oncology · 2014
via PubMed
Wikidata facts
- Mass
- 233.093
Show 4 more facts
- chemical formula
- C₉H₁₆ClN₃O₂
- canonical SMILES
- C1CCC(CC1)NC(=O)N(CCCl)N=O
- World Health Organisation international non-proprietary name
- lomustine
- Commons category
- Lomustine
Sources (8)
via Wikidata · CC0
~15 min read
Article
26 sectionsContents
- Medical uses
- Chemotherapy in human medicine
- Pregnant patients
- Breastfeeding patients
- Pediatric patients
- Geriatric patients
- Chemotherapy in veterinary medicine
- Administration
- Side effects
- Safety
- Toxicities
- Secondary malignancies
- Delayed myelosupression
- Overdose risk
- Drug interactions
- Manufacturing
- Pharmacology
- Mechanism of action
- History
- FDA approval
- Society and culture
- Pricing controversies
- Research
- Clinical trials
- References
- External links
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, 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. It has also been used in veterinary practice as a treatment for cancers in cats and dogs.
Lomustine is a bifunctional alkylating agent, alkylates both DNA and RNA, has the ability to created interstrand cross-links (ICLs) in 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.