Semustine

Semustine
Clinical data
ATC code
Identifiers
  • 1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.162.271 Edit this at Wikidata
Chemical and physical data
FormulaC10H18ClN3O2
Molar mass247.72 g·mol−1
3D model (JSmol)
  • CC1CCC(CC1)NC(=O)N(CCCl)N=O
  • InChI=1S/C10H18ClN3O2/c1-8-2-4-9(5-3-8)12-10(15)14(13-16)7-6-11/h8-9H,2-7H2,1H3,(H,12,15) ☒N
  • Key:FVLVBPDQNARYJU-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

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.[1][2] 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.[2] 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.[3]

  1. ^ Kramer RA, McMenamin MG, Boyd MR (March 1985). "Differential distribution and covalent binding of two labeled forms of methyl-CCNU in the Fischer 344 rat". Cancer Chemotherapy and Pharmacology. 14 (2): 150–155. doi:10.1007/BF00434355. PMID 3971479. S2CID 23111607.
  2. ^ a b Agarwal S, Chadha D, Mehrotra R (3 August 2015). "Molecular modeling and spectroscopic studies of semustine binding with DNA and its comparison with lomustine-DNA adduct formation" (PDF). Journal of Biomolecular Structure & Dynamics. 33 (8): 1653–1668. doi:10.1080/07391102.2014.968874. PMID 25350567. S2CID 205575020.
  3. ^ Boice JD, Greene MH, Killen JY, Ellenberg SS, Keehn RJ, McFadden E, et al. (November 1983). "Leukemia and preleukemia after adjuvant treatment of gastrointestinal cancer with semustine (methyl-CCNU)". The New England Journal of Medicine. 309 (18): 1079–1084. doi:10.1056/NEJM198311033091802. PMID 6353233.