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Merck
CN

S4026

Semustine

Synonym(s):

N-(2-Chloroethyl)-N′-(4-methylcyclohexyl)-N-nitrosourea, Methyl-CCNU

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About This Item

Empirical Formula (Hill Notation):
C10H18ClN3O2
CAS Number:
13909-09-6
Molecular Weight:
247.72
NACRES:
NA.22
PubChem Substance ID:
24899584
UNSPSC Code:
12352100
MDL number:
MFCD00133811

Key Documents

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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)

SMILES string

CC1CCC(CC1)NC(=O)N(CCCl)N=O

InChI key

FVLVBPDQNARYJU-UHFFFAOYSA-N

Related Categories

Application

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

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Carc. 1B - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
091H0080

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Roy E Smith et al.
Journal of the National Cancer Institute, 96(15), 1128-1132 (2004-08-05)
The National Surgical Adjuvant Breast and Bowel Project C-01 trial reported in 1988 that, for patients with adenocarcinoma of the colon, compared with surgery alone, 1) postoperative chemotherapy with 1-(2-chloroethyl)-3-(4-trans-methylcyclohexyl)-1-nitrosourea (i.e., MeCCNU or semustine), vincristine, and 5-fluorouracil was associated with
Nitrosourea chemotherapeutic agents: 1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea.
Report on carcinogens : carcinogen profiles, 12, 327-328 (2011-08-24)
Leonard C Hymes et al.
Pediatric transplantation, 11(5), 536-539 (2007-07-17)
Subclinical acute rejection (SCR) has been increasingly recognized in adult renal transplant recipients with the advent of surveillance biopsies. However, in children, surveillance biopsies are not routinely performed at most centers. Therefore, the incidence, predisposing factors, treatment, and clinical outcomes
Andreas Biffar et al.
European radiology, 20(11), 2679-2689 (2010-06-18)
To evaluate spin-lattice (T1) and spin-spin (T2) relaxation times as well as apparent diffusion coefficients (ADCs) of the fat and water components in the vertebral bone marrow (vBM) of patients with benign and malignant lesions. Forty-four patients were examined at
Ye Guo et al.
Oral oncology, 44(1), 23-30 (2007-02-20)
The objective of this analysis was to evaluate the efficacy and treatment outcome of CHOP and CHOP combined with nitrosourea chemotherapy in natural killer (NK)/T-cell lymphoma of the nasal cavity. Sixty-three patients with NK/T-cell lymphoma of the nasal cavity were
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