42471-28-3

Basic information

• Product Name: Nimustine
• Synonyms: 1-(4-AMINO-2-METHYL-5-PYRIMIDINYL)-METHYL-3-(2-CHLOROETHYL)-3-NITROSOUREA HYDROCHLORIDE;1-((4-amino-2-methylpyrimidin-5-yl)methyl)-3-(2-chloroethyl)-3-nitrosourea;ACNU;NIMUSTINE;NIMUSTINE HCL;N'-[(4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL]-N-(2-CHLORETHYL)-N-NITROSOUREA;3-(4-amino-2-methyl-5-pyrimidinyl)methyl-1-(2-chloroethyl)-1-nitrosourea;n’-((4-amino-2-methyl-5-pyrimidinyl)methyl)-n-(2-chloroethyl)-n-nitroso-ure
• CAS NO: 42471-28-3
• Molecular Formula: C₉H₁₃ClN₆O₂
• Molecular Weight: 272.69
• EINECS: 255-838-1
• Mol File: 42471-28-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 125°C (rough estimate)
• Boiling Point: 98°C (rough estimate)
• Flash Point: 239°C
• Appearance: /solid
• Density: 1.9048 (rough estimate)
• Vapor Pressure: 2.72E-09mmHg at 25°C
• Refractive Index: 1.5790 (estimate)
• PKA: 9.58±0.46(Predicted)
• CAS DataBase Reference: Nimustine(CAS DataBase Reference)
• NIST Chemistry Reference: Nimustine(42471-28-3)
• EPA Substance Registry System: Nimustine(42471-28-3)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 36/37/39-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: YR8450000
• Hazardous Substances Data: 42471-28-3(Hazardous Substances Data)

Usage

Description

Nimustine, also known as ACNU, is an organochlorine compound that is a derivative of urea. It is characterized by the replacement of two hydrogens on one of the amino groups with nitroso and 2-chloroethyl groups, and one hydrogen from the other amino group with a 4-amino-2-methylpyrimidin-5-ylmethyl group. Nimustine is an antitumor agent that is particularly effective against malignant brain tumors.

Uses

Used in Oncology:
Nimustine is used as an antineoplastic agent for the treatment of malignant brain tumors. It works by inhibiting the synthesis of DNA and RNA, thereby preventing the growth and proliferation of cancer cells.
Used in Pharmaceutical Industry:
Nimustine is used in the pharmaceutical industry as a key ingredient in the development of drugs for the treatment of brain tumors and other types of cancer. Its unique chemical structure and mechanism of action make it a valuable component in the fight against cancer.

Originator

Nidran,Sankyo,Japan,1979

Manufacturing Process

0.4 g of sodium nitrite was added with stirring, at 0°C to 5°C, to a solution of 450 mg of 1-(2-chloroethyl)-3-[(2-methyl-4-aminopyridin-5-yl)methyl]urea in 8 ml of 5% hydrochloric acid, and the reaction mixture was then stirred at 0°C to 10°C for an additional 1.5 hours.After completion of the reaction, the reaction mixture was made alkaline by the addition of sodium carbonate, whereupon crystals separated out in situ. The crystals were recovered by filtration, washed with water and then recrystallized from 6 ml of ethanol, to give 0.1 g of the pale yellow pure desired product having a decomposition point of 125°C.

Therapeutic Function

Antitumor, Antileukemic

InChI:InChI=1/C9H13ClN6O2.ClH/c1-6-12-4-7(8(11)14-6)5-13-9(17)16(15-18)3-2-10;/h4H,2-3,5H2,1H3,(H,13,17)(H2,11,12,14);1H

Upstream product

• 42471-43-2 1-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3-(2-chloro-ethyl)-urea 

Relevant articles and documents

Concatamers for Immunemodulation

The invention relates to a polymeric, non-coding nucleic acid molecule for modulation of the activity of the human and animal immune system as well as a method for the manufacture thereof and a vaccine, comprising the polymeric, non-coding nucleic acid molecule, wherein polymeric, non-coding nucleic acid molecules may be understood as non-coding nucleic acid molecules, comprising at least four covalently bound molecules (tetramer) or are assemblies of more non-coding nucleic acid molecules (high molecular polymers) which are covalently bound to each other.