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.
In the Vinony graph
Within Vinony's link graph, semustine is referenced by 278 other articles, and connects out to tiazofurin, China and Connecticut.
Vinony files it under Alkylating antineoplastic agents, Chemical pages without DrugBank identifier and Chloroethyl compounds.
Its subject is documented across 13 Wikipedia language editions.
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
Wikidata facts
- Mass
- 247.109
Show 4 more facts
- chemical formula
- C₁₀H₁₈ClN₃O₂
- canonical SMILES
- CC1CCC(CC1)NC(=O)N(CCCl)N=O
- World Health Organisation international non-proprietary name
- semustine
- Commons category
- Semustine
via Wikidata · CC0
~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.