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Semustine

Semustine Structure
CAS No.
13909-09-6
Chemical Name:
Semustine
Synonyms
Me-CCNU;icig1110;Semustin;SEMUSTINE;ICIG 1110;NSC 95441;nsc-95441;trans-ure;NCI-C04955;Aids126009
CBNumber:
CB1173336
Molecular Formula:
C10H18ClN3O2
Molecular Weight:
247.72
MOL File:
13909-09-6.mol
Modify Date:
2024/7/2 8:55:00

Semustine Properties

Melting point 64°C (rough estimate)
Density 1.3346 (rough estimate)
refractive index 1.5500 (estimate)
storage temp. Store at -20°C,unstable in solution, ready to use.
solubility Soluble in DMSO
pka 10.89±0.40(Predicted)
form Solid
color Light yellow to yellow
CAS DataBase Reference 13909-09-6
IARC 1 (Vol. Sup 7, 100A) 2012
EPA Substance Registry System 1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea (13909-09-6)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06,GHS08
Signal word  Danger
Hazard statements  H300-H311+H331-H315-H319-H335-H350-H360
Precautionary statements  P202-P280-P301+P310-P302+P352+P312-P304+P340+P311-P305+P351+P338
Hazard Codes  T
Risk Statements  45-46-23/24/25-36/37/38
Safety Statements  53-22-26-36/37/39-45
RIDADR  3249
WGK Germany  3
RTECS  YS5000000
HazardClass  6.1(a)
PackingGroup  II
Toxicity child,LDLo,oral,5550mg/kg/30W (5550mg/kg),KIDNEY, URETER, AND BLADDER: CHANGES IN BOTH TUBULES AND GLOMERULI,New England Journal of Medicine. Vol. 300, Pg. 1200, 1979.

Semustine price More Price(1)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) S4026 Semustine 13909-09-6 100MG ₹15057.58 2022-06-14 Buy
Product number Packaging Price Buy
S4026 100MG ₹15057.58 Buy

Semustine Chemical Properties,Uses,Production

Description

In October 2008, scientists of the International Agency for Research on Cancer reaffirmed the Group 1 classification ‘carcinogenic to humans’ of 20 pharmaceutical agents including semustine. Me-CCNU [1-(2-chloroethyl)-3- (4-methylcyclohexyl)-1-nitrosourea] is an alkylating agent of the nitrosourea group, used alone or in combination with other chemotherapeutic agents to treat several types of cancers, including primary and metastatic brain tumors, Lewis lung tumor, and L1210 leukemia. It has also been used to treat cancers of the digestive tract, Hodgkin lymphoma, malignant melanoma, and epidermoid carcinoma of the lung. Doses varied depending on the type of cancer and body weight of the individual. The typical oral dose was 125–200 mgm-2 body surface area, and was repeated every 6 weeks. An alternative regimen was reported to be 200–225 mg m-2 orally every 6–8 weeks. Me-CCNU is a bifunctional antineoplastic agent that undergoes spontaneous chemical decomposition, yielding electrophilic compounds and ultimately inducing alkylation and carbamoylation of cellular macromolecules, including DNA and protein.

Chemical Properties

A crystalline solid or light yellow powder.

Uses

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

Definition

ChEBI: An organochlorine compound that is urea in which the two hydrogens on one of the amino groups are replaced by nitroso and 2-chloroethyl groups and one hydrogen from the other amino group is replaced by a 4-methylcyclohexyl group.

General Description

Light yellow powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

A halogenated and nitrated amide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Fire Hazard

Flash point data for SEMUSTINE are not available. SEMUSTINE is probably combustible.

Safety Profile

Confirmed human carcinogen producing leukemia. Experimental carcinogenic and tumorigenic data. Poison by ingestion, intraperitoneal, intravenous, and possibly other routes. Mutation data reported. Human systemic effects by ingestion: nausea or vomiting, damage to kidney tubules and glomeruli, and hematuria (blood in the urine). When heated to decomposition it emits very toxic fumes of Cland NOx. See also N-NITROSO COMPOUNDS.

Potential Exposure

Semustine is chemotherapy agent; an antineoplastic agent which functions as an alkylating agent.

Carcinogenicity

1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea (methyl-CCNU) is known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans.

Shipping

UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials. PG II.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from strong acids, alkaline materials, strong bases. Semustine, an organic amide, reacts with azo and diazo compounds, releasing toxic gases. Amides are very weak bases but they can react as acids, forming salts. Contact with reducing agents can release flammable gases. Mixing amides with dehydrating agents such as such as phosphorus pentoxide or thionyl chloride generates the corresponding nitrile.

Waste Disposal

It is inappropriate to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, doublebagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

Semustine Preparation Products And Raw materials

Raw materials

Preparation Products

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N-[2-CHLOROETHYL]-N'-[4-METHYLCYCLOHEXYL]-N-NITROSOUREA SEMUSTINE 1-(2-Chloroethyl)-1-([(4-methylcyclohexyl)amino]carbonyl)-2-oxohydrazine 1-(2-chloroethyl)-3-(4-methylcyclohexyl)-1-nitroso-ure 1-(2-Chloroethyl)-3-(4-methyl-cyclohexyl)-1-nitrosourea 1-(2-Chloroethyl)-3-(trans-4-methyl-cyclohexyl)-1-nitrosourea ICIG 1110 icig1110 Lomustine, methyl- Me-CCNU Methyl-CCNU methyl-lomustin N-(2-Chloroethyl)-N'-(trans-4-methylcyclohexyl)-N-nitrosourea n-(2-chloroethyl)-n’-(4-methylcyclohexyl)-n-nitroso-ure n-(2-chloroethyl)-n’-(trans-4-methylcyclohexyl)-n-nitrosourea NCI-C04955 NSC 95441 nsc-95441 trans-Methyl-ccnu trans-ure Urea, 1-(2-chloroethyl)-3-(4-methylcyclohexyl)-1-nitroso- Urea, 1-(2-chloroethyl)-3-(4-methylcyclohexyl)-1-nitroso-, (E)- Urea, 1-(2-chloroethyl)-3-(4-methylcyclohexyl)-1-nitroso-, trans- Urea, N-(2-chloroethyl)-N'-(4-methylcyclohexyl)-N-nitroso- N-(4-METHYLCYCLOHEXYL)-N-(2-CHLOROETHYL)-N-NITROSOUREA 1-(2-Chloroethyl)-3-(trans-4-methylcyclohexane)-1-nitrosourea 1-(2-Choroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea Aids126009 Aids-126009 Semustine,N-(2-Chloroethyl)-N′-(4-methylcyclohexyl)-N-nitrosourea Semustin SEMUSTINE(ME-CCNU) FACT.STANDARD Semustine USP/EP/BP 13909-09-6 C10H18ClN3O2 Nitroso Compounds Nitrogen Compounds Organic Building Blocks Building Blocks ATROMID Building Blocks Chemical Synthesis Nitrogen Compounds Nitroso Compounds Organic Building Blocks