13909-09-6
Chemical Structure
Semustine
- CAS No.: 13909-09-6
- Formula:C10H18ClN3O2
- Molecular Weight:247.72
IUPAC Name: 1-(2-chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea
InChIKey: FVLVBPDQNARYJU-UHFFFAOYSA-N
SMILES: O=C(NC1CCC(C)CC1)N(CCCl)N=O
Biological Activity: Semustine is an orally active, blood-brain barrier permeable antitumor alkylating agent with a binding affinity of 1.53 × 103 M-1 for guanine and thymine residues in bovine DNA. Semustine undergoes major groove-directed alkylation at guanine residues to form O6-chloroethylguanine and N1-O6-ethanoguanine adducts, and generates dG-dC interstrand crosslinks. Semustine induces partial B- to C-type transition of DNA, base stacking and helical structure distortion, mild dehydration, as well as partial DNA double-strand unwinding. Semustine can be used in research related to Lewis lung cancer, leukemia, Hodgkin's lymphoma, malignant melanoma, glioma, and diffuse large B-cell lymphoma[1][2].
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Semustine | 98.0% | Semustine is an orally active, blood-brain barrier permeable antitumor alkylating agent with a binding affinity of 1.53 × 103 M-1 for guanine and thymine residues in bovine DNA. Semustine undergoes major groove-directed alkylation at guanine residues to form O6-chloroethylguanine and N1-O6-ethanoguanine adducts, and generates dG-dC interstrand crosslinks. Semustine induces partial B- to C-type transition of DNA, base stacking and helical structure distortion, mild dehydration, as well as partial DNA double-strand unwinding. Semustine can be used in research related to Lewis lung cancer, leukemia, Hodgkin's lymphoma, malignant melanoma, glioma, and diffuse large B-cell lymphoma. | ||||||||||||||||||||
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- [1]. Agarwal S, et al. Molecular modeling and spectroscopic studies of semustine binding with DNA and its comparison with lomustine-DNA adduct formation. J Biomol Struct Dyn. 2015;33(8):1653-68. [Content Brief]
- [2]. Wang T, et al. 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. Ann Hematol. 2024;103(2):575-582. [Content Brief]
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