Carmustine Systematic (IUPAC) name N,N'-bis(2-chloroethyl)-N-nitroso-urea Clinical data AHFS/Drugs.com MedlinePlus Pregnancy cat. D(US) Legal status ℞ Prescription only Routes Intravenous, wafer for implant Pharmacokinetic data Bioavailability 5 to 28% (oral) Protein binding 80% Metabolism Hepatic (CYP1 A2-mediated) Half-life 15 to 30 min Identifiers CAS number ATC code L01 PubChem DrugBank ChemSpider UNII KEGG ChEBI ChEMBL Chemical data Formula C5H9Cl2N3O2 Mol. mass 214.049 g/mol SMILES & (what is this?)
Carmustine or BCNU (bis-chloroethylnitrosourea) is a mustard gas-related β-chloro-nitrosourea compound used as an alkylating agent in chemotherapy. As a dialkylating agent, BCNU is able to form interstrand crosslinks in DNA which prevents DNA replication and DNA transcription.
It has the appearance of a orange-yellow solid.
Carmustine for injection is marketed under the name BiCNU by Bristol-Myers Squibb.
It is used in the treatment of several types of brain cancer (including glioma, glioblastoma multiforme, medulloblastoma and astrocytoma), multiple myeloma and lymphoma (Hodgkin's and non-Hodgkin). BCNU is sometimes used in conjunction with alkyl guanine transferase (AGT) inhibitors, such as O6-benzylguanine. The AGT-inhibitors increase the efficacy of BCNU by inhibiting the Direct Reversal pathway of DNA repair, which will prevent formation of the interstrand crosslink between the N1 of guanine and the N3 of cytosine.
Bone marrow may take 6 weeks to recover function following treatment with carmustine. Weekly monitoring of platelet and white blood cell counts are recommended as a basis for patient-specific adjustments to dosage regimens. Bone marrow and pulmonary toxicities are a function of lifetime cumulative dose.
Pulmonary toxicity characterised by pulmonary infiltrates and/or fibrosis (scarring of the lungs). Cases of fatal pulmonary toxicity have been reported. Delayed onset pulmonary fibrosis
Delayed myelosuppression. Thrombocytopenia usually occurs about 4 weeks post administration. Leukopenia occurs approximately 5–6 weeks after administration. Cumulative myelosuppression, manifested by more depressed indices. Anemia also occurs, but is less frequent and less severe than thrombocytopenia or leukopenia. The occurrence of acute leukemia and bone marrow dysplasias have been reported in patients following long-term nitrosourea therapy.
Nausea and vomiting after IV administration are noted frequently. This usually occurs within 2 hours of administration. This is usually dose related. Prior administration of antiemetics is effective in diminishing and sometimes preventing side effects.
A reversible type of hepatic toxicity, manifested by increased transaminase, alkaline phosphatase and bilirubin levels, has been reported in a small percentage of patients.
Renal abnormalities consisting of progressive azotemia, decrease in kidney size and renal failure have been reported in patients who received large cumulative doses after prolonged therapy. Kidney damage has also been reported occasionally in patients receiving lower total doses.
In the treatment of brain tumours, the U.S. Food and Drug Administration (FDA) approved biodegradable discs, Gliadel, infused with carmustine can be used. They are implanted under the skull during a surgery called a craniotomy.
- ^ Ewend MG, Brem S, Gilbert M, et al. (June 2007). "Treatment of single brain metastasis with resection, intracavity carmustine polymer wafers, and radiation therapy is safe and provides excellent local control". Clin. Cancer Res. 13 (12): 3637–41. doi:10.1158/1078-0432.CCR-06-2095. PMID 17575228. http://clincancerres.aacrjournals.org/cgi/pmidlookup?view=long&pmid=17575228.
- ^ http://www.cancerbackup.org.uk/Treatments/Chemotherapy/Individualdrugs/Gliadelimplants
Intracellular chemotherapeutic agents/antineoplastic agents (L01) SPs/MIs
(M phase)Block microtubule assemblyBlock microtubule disassembly
inhibitorIIICrosslinking of DNA
(CCNS)Aziridines: Carboquone • ThioTEPA • Triaziquone • Triethylenemelamine
Photosensitizers/PDT OtherOther/ungroupedAmsacrine • Trabectedin • retinoids (Alitretinoin, Tretinoin) • Arsenic trioxide • asparagine depleters (Asparaginase/Pegaspargase) • Celecoxib • Demecolcine • Elesclomol • Elsamitrucin • Etoglucid • Lonidamine • HAMLET (human alpha-lactalbumin made lethal to tumor cells) • Lucanthone • Mitoguazone • Mitotane • Oblimersen • Omacetaxine mepesuccinate • mTOR inhibitors (Everolimus, Temsirolimus)
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