semustine
Sign in to saveAlso known as 1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea, 1-(2-Chloroethyl)-1-([(4-methylcyclohexyl)amino]carbonyl)-2-oxohydrazine, N-(2-Chloroethyl)-N'-(4-methylcyclohexyl)-N-nitrosourea, Methyl-CCNU
Semustine (1-(2-chloroethyl)-3-(trans-4-methylcyclohexyl)-1-nitrosourea, MeCCNU) is an alkylating nitrosourea compound used in chemotherapy treatment of various types of tumours. Due to its lipophilic property, semustine can cross the blood-brain barrier for the chemotherapy of brain tumours, where it interferes with DNA replication in the rapidly-dividing tumour cells. Semustine, just as lomustine, is administered orally. Evidence has been found that treatment with semustine can cause acute leukaemia as a delayed effect in very rare cases.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 443222760
- Drug.IUPAC_name
- 1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea
- Drug.image
- Semustine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.CAS_number
- 13909-09-6
- Drug.ATC_prefix
- L01
- Drug.ATC_suffix
- AD03
- Drug.PubChem
- 5198
- Drug.UNII
- 6YY7T1T567
- Drug.KEGG
- D05822
- Drug.ChEBI
- 6863
- Drug.ChemSpiderID
- 5009
- Drug.C
- 10
- Drug.H
- 18
- Drug.Cl
- 1
via Wikipedia infobox
Research
520 papers- Nephrotoxicity of semustine.Cancer treatment reports · 1983
- Identification of potential immunotherapy biomarkers for breast cancer by bioinformatics analysis.Bioscience reports · 2022
- CEAC (oral semustine, etoposide, cytarabine and cyclophosphamide) vs BEAM (carmustine, etoposide, cytarabine, and melphalan) conditioning regimen of autologous stem cell transplantation for diffuse large B-cell lymphoma: a post-hoc, propensity score-matched, cohort study in Chinese patients.Annals of hematology · 2024
- Efficacy and toxicity of SEAM (semustine, etoposide, cytarabine, and melphalan) conditioning regimen followed by autologous stem cell transplantation in lymphoma.Hematology (Amsterdam, Netherlands) · 2022
- Molecular modeling and spectroscopic studies of semustine binding with DNA and its comparison with lomustine-DNA adduct formation.Journal of biomolecular structure & dynamics · 2015
via PubMed
~8 min read
Encyclopedic overview
11 sectionsContents
- Structure and reactivity
- Synthesis
- Available forms
- Mechanism of action
- Metabolism
- Indications
- Efficacy and side effects
- Efficacy
- Adverse effects
- Effects on animals
- References
Semustine (1-(2-chloroethyl)-3-(trans-4-methylcyclohexyl)-1-nitrosourea, MeCCNU) is an alkylating nitrosourea compound used in chemotherapy treatment of various types of tumours. Due to its lipophilic property, semustine can cross the blood-brain barrier for the chemotherapy of brain tumours, where it interferes with DNA replication in the rapidly-dividing tumour cells. Semustine, just as lomustine, is administered orally. Evidence has been found that treatment with semustine can cause acute leukaemia as a delayed effect in very rare cases.
== Structure and reactivity == Semustine (Me-CCNU) is an organochlorine compound that is urea in which the two hydrogens on one of the amino groups are replaced by nitroso and 2-chloroetyl groups and one hydrogen from the other amino group is replaced by a 4-methylcyclohexcyl group. Semustine is also known as a 4-methyl derivative of lomustine.
Excerpted from Wikipedia’s “semustine” article, available under the CC BY-SA 4.0 licence.