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Lomustine

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Lomustine Basic information
Lomustine Chemical Properties
  • Melting point:88-90
  • Boiling point:63.6°C (rough estimate)
  • Density 1.3840 (rough estimate)
  • refractive index 1.5790 (estimate)
  • storage temp. 2-8°C
  • solubility Practically insoluble in water, freely soluble in acetone and in methylene chloride, soluble in ethanol (96 per cent).
  • form neat
  • pka10.88±0.20(Predicted)
  • Merck 14,5564
  • InChIKeyGQYIWUVLTXOXAJ-UHFFFAOYSA-N
  • CAS DataBase Reference13010-47-4(CAS DataBase Reference)
  • IARC2A (Vol. 26, Sup 7) 1987
  • EPA Substance Registry System1-(2-Chloroethyl)-3-cyclohexyl-1-nitrosourea (13010-47-4)
Safety Information
  • Hazard Codes T
  • Risk Statements 45-25
  • Safety Statements 53-45
  • RIDADR 3249
  • WGK Germany 3
  • RTECS YS4900000
  • HazardClass 6.1(a)
  • PackingGroup II
  • HS Code 29299090
  • Hazardous Substances Data13010-47-4(Hazardous Substances Data)
  • ToxicityLD50 in male mice (mg/kg): 51 orally; 56 i.p.; 61 s.c. (Thompson, Larson)
MSDS
Lomustine Usage And Synthesis
  • Chemical PropertiesLomustine is a pale yellow powder.
  • UsesCCNU is an oral anticancer drug that was approved by the U.S. Food and Drug Administration in 1976 for marketing, as lomustine (FDA 2009a). CCNU is used alone or in combination with other antineoplastic agents, including procarbazine and vincristine, etoposide and prednimustine, and other combinations (IARC 1981, HSDB 2009). It is used primarily in the treatment of Hodgkin’s disease and brain tumors, but it has also been used to treat other cancer, includ-ing lung cancer, non-Hodgkin’s lymphoma, malignant melanoma, breast cancer, kidney cancer, and cancer of the gastrointestinal tract (MedlinePlus 2009). It has also been applied to the skin to treat mycosis fungoides and psoriasis.
  • UsesLomustine USP is used to treat Malignant brain tumors; Hodgkin’s disease.
  • UsesChloroethylnitrosourea derivative with antitumor activity. Similar to carmustine, chlorozotocin, nimustine, ranimustine. Antineoplastic.
  • DefinitionChEBI: An N-nitrosourea that is urea in which one of the nitrogens is substituted by a 2-chloroethyl group and by a nitroso group, while the other nitrogen is substituted by a cyclohexyl group. An alkylating antineoplastic agent, it is used in he treatment of brain tumours, lung cancer, malignant melanoma and other solid tumours.
  • brand nameCeenu (Bristol-Myers Squibb).
  • Synthesis Reference(s)Journal of Medicinal Chemistry, 18, p. 104, 1975 DOI: 10.1021/jm00235a023
    Synthesis, p. 1027, 1987 DOI: 10.1055/s-1987-28160
  • General DescriptionLomustine is available in 10-, 40-, and 100-mg capsules fororal administration in the treatment of primary and metastaticbrain cancers and Hodgkin’s lymphoma. This lipophilicagent is well absorbed, widely distributed, and crosses theblood-brain barrier. Lomustine undergoes extensive hepaticmetabolism, which is mediated by CYP3A4 to give severalhydroxylated metabolites, which arise as a result of oxidationof the cyclohexyl ring. Several of these are more activethan the parent compound. Denitrosation and dechlorinationhave also been demonstrated to occur for lomustine as well.The intact drug was not found in plasma when the agent wasadministered orally. Elimination occurs primarily in theurine with an elimination half-life of 16 to 72 hours.Myelosuppression is dose limiting and presents in a mannersimilar to that seen with carmustine. Other toxicities includenausea, vomiting, anorexia, impotence, sterility, amenorrhea,and infertility. Pulmonary and renal toxicity are rarelyseen during standard-dose therapy but increase during highdosetherapy.
  • Mechanism of actionLike other nitrosoureas, lomustine acts as a DNA-alkylating agent, and it also inhibits various key enzymatic reactions by carbamoylating proteins.
  • Safety ProfileConfirmed carcinogen with experimental carcinogenic and tumorigenic data. Poison by ingestion, intraperitoneal, subcutaneous, intravenous, and possibly other routes. Human systemic effects by ingestion: anorexia, nausea or vomiting, leukopenia (decrease in the white blood cell count), and thrombocytopenia (decrease in the number of blood platelets). Experimental teratogenic and reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of Cland NOx. See also NNITROSO COMPOUNDS.
  • Chemical SynthesisLomustine, 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea (30.2.4.3), is made by reacting ethanolamine with cyclohexylisocyanate, which forms 1-(2-hydroxyethyl)-3- cyclohexylurea (30.2.4.1). Upon reaction with thionyl chloride, the hydroxyl group in it is replaced with a chlorine atom, giving 1-(2-chloroethyl)-3-cyclohexylurea (30.2.4.2). This is nitrated in non-aqueous conditions with formic acid and sodium nitrite to give lomustine (30.2.4.3).

  • Potential ExposureA potential danger to those involved in the manufacture, administration or consumption of this antineoplastic (anti-cancer) agent
  • Veterinary Drugs and TreatmentsLomustine may be useful in the adjunctive treatment of CNS neoplasms, lymphomas, and mast cell tumors in dogs and cats.
  • Carcinogenicity1-(2-Chloroethyl)-3-cyclohexyl-1-nitrosourea (CCNU) is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
  • ShippingUN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials
  • Waste DisposalIt is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
Lomustine Preparation Products And Raw materials
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