Lomustine

Base Information

• Chemical Name: Lomustine
• CAS No.: 13010-47-4
• Molecular Formula: C9H16ClN3O2
• Molecular Weight: 233.698
• Hs Code.: 29299090
• European Community (EC) Number: 235-859-2
• NSC Number: 759635,79037
• UNII: 7BRF0Z81KG
• DSSTox Substance ID: DTXSID2023222
• Nikkaji Number: J3.122D
• Wikipedia: Lomustine
• Wikidata: Q415378
• NCI Thesaurus Code: C617
• RXCUI: 6466
• Metabolomics Workbench ID: 43420
• ChEMBL ID: CHEMBL514
• Mol file: 13010-47-4.mol

Synonyms:Belustine;CCNU;Cecenu;CeeNU;Lomustine;NSC 79037;NSC-79037;NSC79037

Chemical Property of Lomustine

Chemical Property:

• Appearance/Colour: Yellow powder
• Vapor Pressure: 0.00142mmHg at 25°C
• Melting Point: 88-90 °C
• Refractive Index: 1.57
• Boiling Point: 296.6°C at 760 mmHg
• PKA: 10.88±0.20(Predicted)
• Flash Point: 133.2°C
• PSA: 61.77000
• Density: 1.35 g/cm³
• LogP: 2.64180
• Storage Temp.: −20°C
• Solubility.: Practically insoluble in water, freely soluble in acetone and in methylene chloride, soluble in ethanol (96 per cent).
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 233.0931045
• Heavy Atom Count: 15
• Complexity: 219

Purity/Quality:

98.5%, ^*data from raw suppliers

Lomustine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-25
• Safety Statements: 53-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antineoplastic Agents, Alkylating Agents
• Canonical SMILES: C1CCC(CC1)NC(=O)N(CCCl)N=O
• Recent ClinicalTrials: 9-ING-41 in Patients With Advanced Cancers
• Recent EU Clinical Trials: A Multicenter, Open-Label Study with a Randomized Control Arm of the Efficacy, Safety, and Pharmacokinetics of Intravenously Infused Berubicin in Adult Patients with Recurrent Glioblastoma Multiforme (WHO Grade IV) After Failure of Standard First Line Therapy
• 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. Lomustine USP is used to treat Malignant brain tumors; Hodgkin’s disease. Chloroethylnitrosourea derivative with antitumor activity. Similar to carmustine, chlorozotocin, nimustine, ranimustine. Antineoplastic.
• Clinical Use: #N/A

Technology Process of Lomustine

There total 15 articles about Lomustine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

N-(2-chloroethyl)-N'-cyclohexylurea (13908-11-7) → 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea (13010-47-4)

Guidance literature:

With tin(IV) chloride; sodium nitrite; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1055/s-2006-942397

Reference yield: 81.0%

N-(2-chloroethyl)-N-nitrosocarbamic acid N-hydroxypyrrolidine-2,5-dione ester (80354-49-0) + cyclohexylamine (108-91-8,157973-60-9) → 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea (13010-47-4)

Guidance literature:

Ambient temperature;

DOI:10.1016/S0040-4039(00)85958-4

Reference yield: 80.0%

N-(chloro-2 ethyl)N-nitrosocarbamate de trichloro-2,4,5 phenyle (80354-51-4) + cyclohexylamine (108-91-8,157973-60-9) → 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea (13010-47-4)

Guidance literature:

In N,N-dimethyl-formamide; at 0 ℃; for 2h;

DOI:10.1021/jm00344a017

upstream raw materials:

N-(2-chloroethyl)-N'-cyclohexylurea

2-(cyclohexylimino)-3-nitroso-2-oxazolidine

p-nitrophenyl N-(2-chloroethyl)-N-nitroso-carbamate

cyclohexylamine

Downstream raw materials:

ethylene glycol

acetaldehyde

2-chloro-ethanol

Diazoethan

Refernces

• 1、 Jaman, Zinia,Sobreira, Tiago J. P.,Mufti, Ahmed,Ferreira, Christina R.,Cooks, R. Graham,Thompson, David H.. "Rapid On-Demand Synthesis of Lomustine under Continuous Flow Conditions". . p. 334 - 341. Retrieved 2019.
• 2、 -. "On-Demand Rapid Synthesis of Lomustine Under Continuous Flow Conditions". Paragraph 0053; 0090-0093. . Retrieved 2020/05/02.
• 3、 -. "THERAPEUTIC FOR HEPATIC CANCER". . . Retrieved 2011/02/18.