Semustine
- Methyllomustin
- 4- Methyllomustin
- Methyl - CCNU
- MeCCNU
- NSC 95441
- 1 - (2 -chloroethyl ) -3 - (4- methylcyclohexyl) -1 -nitrosourea (IUPAC)
L01AD03
Cytostatic
Risk
Template: Infobox chemical / molecular formula search available
Semustine ( synonym: methyl -chloroethyl -cyclohexyl -nitroso- urea = MeCCNU ), chemically 1 - (2 -chloroethyl ) -3 - (4- methylcyclohexyl) -1 -nitrosourea, is the generic name for a cytostatic agent from the group of nitrosoureas. It is the 4 -methyl derivative of lomustine.
- 2.1 Mechanism of Action
- 2.2 Side Effects
Chemical Properties
Stereochemistry
Semustine is a compound of two isomers, called cis / trans isomers exist on the basis of the unsterschiedlichen substitution possibilities on the cyclohexane ring. Such isomers may differ in certain physical properties, and physiological effects. By a suitable synthetic strategies or separation processes can be selectively isolate the individual compounds.
Pharmacology
Mechanism of Action
Semustine changed as nitrosoureas all the genetic material in the cell nuclei. This causes the affected cells can no longer divide and die after some time. From the genomic damage are essentially rapidly dividing cells - especially cancerous cells - affected. Semustine is able to overcome the blood- brain barrier. This is in the treatment of melanoma with CNS metastasis advantageous.
Side effects
Semustine is myelotoxic, meaning it damages the bone marrow. This damage has a negative effect on blood formation, especially the platelets and leucocytes. In addition, nausea and hair loss are the main side effects.
Semustine - like all nitrosoureas - carcinogenic itself, that is carcinogenic. In animal experiments, it increased in rats after intraperitoneal administration, the total incidence of tumors in female mice and the incidence of leukemia and malignant lymphoma. For humans it is classified as carcinogenic since the early 1990s. Increases the risk of leukemia after treatment with semustine significantly.