1,3-bis(2-chloroethyl)-1-nitrosourea

• ChemBase ID: 147
• Molecular Formular: C5H9Cl2N3O2
• Molecular Mass: 214.04986
• Monoisotopic Mass: 213.0071819
• SMILES: ClCCN(N=O)C(=O)NCCCl
• Canonical SMILES: ClCCNC(=O)N(CCCl)N=O
• InChI: InChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)
• InChIKey: DLGOEMSEDOSKAD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-bis(2-chloroethyl)-1-nitrosourea; 1,3-bis(2-chloroethyl)-3-nitrosourea
• IUPAC Traditional name: 1,3-bis(2-chloroethyl)-1-nitrosourea; carmustine
• Brand Name: Becenun; Bi CNU; Carmubris; Gliadel; Gliadel Wafer; Nitrumon; BiCNU
• Synonyms: BCNU, N,N’-Bis(2-chloroethyl)-N-nitrosourea, NSC-409962, Becenun, Bicnu,; BCNU; Bischlorethylnitrosourea; Bischlorethylnitrosurea; Carmustin; Carmustine; 1,3-Bis(2-chloroethyl)-1-nitrosourea; Carmustine; Becenum; Carmubris; Nitrumon

Database IDs

• CAS Number: 154-93-8
• EC Number: 205-838-2
• MDL Number: MFCD00057706
• PubChem SID: 160963610; 24278289; 46506980
• PubChem CID: 2578

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.963143
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.0226562
• LogD (pH = 7.4): 1.0226457
• Log P: 1.0226563
• Molar Refractivity: 46.9797 cm^3
• Polarizability: 17.322094 Å^3
• Polar Surface Area: 61.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.24
• LOG S: -2.15
• Solubility (Water): 1.53e+00 g/l

PROPERTIES

Physical Property

• Solubility: < 0.1 g/100 mL at 18 °C; DMSO; Methanol
• Apperance: (Oily liquid to amorphous solid); Light Yellow to Pale Orange Solid
• Melting Point: 30 °C(lit.); 30-32°C
• Hydrophobicity(logP): 1.5

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: YS2625000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 45-46-60-61-28
• Safety Statements: 53-22-36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H350-H360
• GHS Precautionary statements: P201-P264-P301 + P310-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... GSR(2936)
• Mechanism of Action: Alkylating agent in cancer chemotherapy

Product Information

• Purity: ≥98%
• Application(s): Antineoplastic agent; Used to treat gliomas, glioblastoma multiforme, medulloblastoma and astrocytoma, multiple myeloma and lymphoma (Hodgkin's and non-Hodgkin).
• Empirical Formula (Hill Notation): C5H9Cl2N3O2

DETAILS

DrugBank - DB00262

• Drug Groups: approved
• Description: A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed)
• Indication: For the treatment of brain tumors, multiple myeloma, Hodgkin's disease and Non-Hodgkin's lymphomas.
• Pharmacology: Carmustine is one of the nitrosoureas indicated as palliative therapy as a single agent or in established combination therapy with other approved chemotherapeutic agents in treatment of brain tumors, multiple myeloma, Hodgkin's disease, and non-Hodgkin's lymphomas. Although it is generally agreed that carmustine alkylates DNA and RNA, it is not cross resistant with other alkylators. As with other nitrosoureas, it may also inhibit several key enzymatic processes by carbamoylation of amino acids in proteins.
• Toxicity: The oral LD₅₀s in rat and mouse are 20 mg/kg and 45 mg/kg, respectively. Side effects include leukopenia, thrombocytopenia, nausea. Toxic effects include pulmonary fibrosis (20-0%) and bone marrow toxicity.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic and rapid with active metabolites. Metabolites may persist in the plasma for several days.
• Absorption: 5 to 28% bioavailability
• Half Life: 15-30 minutes
• Protein Binding: 80%
• Elimination: Approximately 60% to 70% of a total dose is excreted in the urine in 96 hours and about 10% as respiratory CO2.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - C0400

Biochem/physiol Actions
Carmustine is a DNA alkylating agent causing DNA interstrand crosslinks.1 Effective against glioma and other solid tumors.

Toronto Research Chemicals - C183875

An alkylating and carbamoylating nitrosourea compound. It interacts with DNA, RNA and proteins causing DNA interstrand cross linking which is cytotoxic and leads to apoptotic cell death.

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