Semustine

Semustine
Clinical data
ATC code	L01AD03 (WHO) ;
Identifiers
	IUPAC name 1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea;
CAS Number	13909-09-6 ;
PubChem CID	5198;
ChemSpider	5009 ;
UNII	6YY7T1T567;
KEGG	D05822 ;
ChEBI	CHEBI:6863 ;
CompTox Dashboard (EPA)	DTXSID8031603 ;
ECHA InfoCard	100.162.271
Chemical and physical data
Formula	C10H18ClN3O2
Molar mass	247.72 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1CCC(CC1)NC(=O)N(CCCl)N=O;
	InChI 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) ; Key:FVLVBPDQNARYJU-UHFFFAOYSA-N ;
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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]

^ 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.
^ ^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.
^ 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.

[Kramer-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.

[Agarwal-2] 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.

[Boice-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.

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