Lomustine 13010-47-4 CAS NO.13010-47-4

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Lomustine Basic information

Product Name:	Lomustine
Synonyms:	(chloro-2-ethyl)-1-cyclohexyl-3-nitrosourea;(cloro-2-etil)-1-cicloesil-3-nitrosourea;1-(2-chloroethyl)-3-cyclohexyl-1-nitrosoure;1-(2-chloroethyl)-3-cyclohexyl-1-nitroso-ure;belustine;nci-c04740;nsc79037;nsc-79037
CAS:	13010-47-4
MF:	C9H16ClN3O2
MW:	233.7
EINECS:	235-859-2
Product Categories:	Other APIs;API;Intermediates & Fine Chemicals;Nitric Oxide Reagents;Pharmaceuticals;CEENU;Pharmaceutical
Mol File:	13010-47-4.mol

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
pka	10.88±0.20(Predicted)
Merck	14,5564
InChIKey	GQYIWUVLTXOXAJ-UHFFFAOYSA-N
CAS DataBase Reference	13010-47-4(CAS DataBase Reference)
IARC	2A (Vol. 26, Sup 7) 1987
EPA Substance Registry System	1-(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 Data	13010-47-4(Hazardous Substances Data)
Toxicity	LD50 in male mice (mg/kg): 51 orally; 56 i.p.; 61 s.c. (Thompson, Larson)

MSDS Information

Provider	Language
1-(2-Chloroethyl)-3-cyclohexyl-1-nitrosourea	English

Lomustine Usage And Synthesis

Chemical Properties	Lomustine is a pale yellow powder.
Uses	CCNU 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.
Uses	Lomustine USP is used to treat Malignant brain tumors; Hodgkin’s disease.
Uses	Chloroethylnitrosourea derivative with antitumor activity. Similar to carmustine, chlorozotocin, nimustine, ranimustine. Antineoplastic.
Definition	ChEBI: 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 name	Ceenu (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 Description	Lomustine 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.
Biochem/physiol Actions	Antineoplastic agent with cellular DNA effects. Lomustine induces p53 expression in A2870 cells.
Mechanism of action	Like other nitrosoureas, lomustine acts as a DNA-alkylating agent, and it also inhibits various key enzymatic reactions by carbamoylating proteins.
Clinical Use	#N/A
Safety Profile	Confirmed 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 Synthesis	Lomustine, 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 Exposure	A potential danger to those involved in the manufacture, administration or consumption of this antineoplastic (anti-cancer) agent
Veterinary Drugs and Treatments	Lomustine may be useful in the adjunctive treatment of CNS neoplasms, lymphomas, and mast cell tumors in dogs and cats.
Carcinogenicity	1-(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.
Metabolism	Molecular weight (daltons) 233.7 % Protein binding 60 % Excreted unchanged in urine 50 (as metabolites) Volume of distribution (L/kg) No data Half-life - normal/ESRF (hrs) 16-48 (metabolites)
Shipping	UN2811 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 Disposal	It 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.

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