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S4026

Sigma-Aldrich

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
MDL number:
MFCD00133811
UNSPSC Code:
12352100
PubChem Substance ID:
24899584
NACRES:
NA.22

SMILES string

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)

InChI key

FVLVBPDQNARYJU-UHFFFAOYSA-N

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

Signal Word

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 Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Evrim Sahin et al.
Reproduction, fertility, and development, 21(3), 469-478 (2009-03-06)
Mature spermatozoa have a mechanism by which they can reduce cellular swelling caused by hypo-osmotic stress. The development of this ability during epididymal maturation in the bull was investigated. Caput and cauda sperm preparations were exposed to various osmotic stresses
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
Nitrosourea chemotherapeutic agents: 1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea.
Report on carcinogens : carcinogen profiles, 12, 327-328 (2011-08-24)
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