3-(2-chloroethyl)-1-(4-methylcyclohexyl)-3-nitrosourea

• ChemBase ID: 133366
• Molecular Formular: C10H18ClN3O2
• Molecular Mass: 247.72182
• Monoisotopic Mass: 247.10875451
• SMILES: CC1CCC(CC1)NC(=O)N(CCCl)N=O
• Canonical SMILES: ClCCN(C(=O)NC1CCC(CC1)C)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)
• InChIKey: FVLVBPDQNARYJU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-chloroethyl)-1-(4-methylcyclohexyl)-3-nitrosourea
• IUPAC Traditional name: semustine
• Synonyms: Methyl-CCNU; Semustine; N-(2-氯乙基)-N′-(4-甲基环己基)-N-亚硝脲; 司莫司汀

Database IDs

• CAS Number: 13909-09-6
• MDL Number: MFCD00133811
• PubChem SID: 162227643; 24899584
• PubChem CID: 5198

CALCULATED PROPERTIES

• Acid pKa: 13.398404
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.444456
• LogD (pH = 7.4): 2.4444556
• Log P: 2.444456
• Molar Refractivity: 63.1992 cm^3
• Polarizability: 23.741993 Å^3
• Polar Surface Area: 61.77 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: YS5000000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 45-46-23/24/25-36/37/38
• Safety Statements: 53-22-26-36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H311-H315-H319-H331-H335-H350-H360
• GHS Precautionary statements: P201-P261-P264-P280-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2

DETAILS

Sigma Aldrich - S4026

Application
Commonly used in pharmacological studies involving:
• Nutrient-sensitized screening for drugs that shift the energy metabolism from mitchondrial respiration to glycolysis1
• CEOP regimen with semustine used as induction chemotherapy in patients with lymphoma2
• Investigations into its use for chemotherapy3,4