Semustine

Base Information

• Chemical Name: Semustine
• CAS No.: 13909-09-6
• Deprecated CAS: 56748-54-0
• Molecular Formula: C10H18ClN3O2
• Molecular Weight: 247.725
• Hs Code.: 2924299090
• European Community (EC) Number: 634-275-9
• NSC Number: 758471,135091,95441
• UN Number: 3249
• UNII: 2281H4FBL9,EGU4CMI14D
• DSSTox Substance ID: DTXSID8031603,DTXSID301170045
• Nikkaji Number: J60.486K,J83.888H,J8.456E
• Wikipedia: Semustine
• Wikidata: Q1230937,Q27277177
• NCI Thesaurus Code: C827
• Metabolomics Workbench ID: 67496
• ChEMBL ID: CHEMBL12948,CHEMBL1967746,CHEMBL2051944
• Mol file: 13909-09-6.mol

Synonyms:Me CCNU;Me-CCNU;MeCCNU;Methyl CCNU;Methyl-CCNU;NSC 95441;NSC-95441;NSC95441;Semustine

Chemical Property of Semustine

Chemical Property:

• Appearance/Colour: Light yellow powder
• Melting Point: 64°C (rough estimate)
• Refractive Index: 1.51
• PKA: 10.89±0.40(Predicted)
• PSA: 61.77000
• Density: 1.315 g/cm³
• LogP: 2.88780
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 247.1087545
• Heavy Atom Count: 16
• Complexity: 242
• Transport DOT Label: Poison

Purity/Quality:

98%,99%, ^*data from raw suppliers

Semustine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-46-23/24/25-36/37/38
• Safety Statements: 53-22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC(CC1)NC(=O)N(CCCl)N=O
• Recent ClinicalTrials: A Study Comparing Haploidentical Hematopoietic Stem Cell Transplantations (HSCTs) From Young Non-first-degree and Older First-degree Donors in Hematological Malignancies
• 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.
• Uses: Me-CCNU is an investigational drug used in chemotherapy to treat various types of cancers like Hodgkin’s disease, malignant gliomas, gastrointestinal tract adenocarcinomas, breast carcinomas, squamous-cell carcinomas, malignant melanoma, and epidermoid carcinoma of the lung. It is an antineoplastic agent that functions as an alkylating agent. An emerging trend in this arena has been to design hybrid steroid compounds of anticancer agents, because they presumably produce less toxicity, significantly lower than the cytotoxic components alone, and increase anticancer activity of alkylating esters. 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 antihyperlipidemic

Technology Process of Semustine

There total 2 articles about Semustine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-(4-methylcyclohexyl)-3-(2-chloroethyl)urea (13908-15-1) → N-<2-chloroethyl>-N'-<4-methylcyclohexyl>-N-nitrosourea (13909-09-6)

Guidance literature:

With tin(IV) chloride; sodium nitrite; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1055/s-2006-942397

Reference yield:

4-methylcyclohexylamine (6321-23-9) → N-<2-chloroethyl>-N'-<4-methylcyclohexyl>-N-nitrosourea (13909-09-6)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether

2: NaNO₂, HCO₂H

With formic acid; sodium nitrite; In diethyl ether;

DOI:10.1021/jm00324a026

Reference yield:

N-<2-chloroethyl>-N'-<4-methylcyclohexyl>-N-nitrosourea (13909-09-6) → ethanol (64-17-5) + 1-(4-methylcyclohexyl)-3-(2-chloroethyl)urea (13908-15-1) + ethylamine (75-04-7,85404-22-4) + 4-methylcyclohexylamine (6321-23-9)

Guidance literature:

With potassium hydroxide; aluminum nickel; In methanol; Product distribution; Mechanism; degradation under various conditions (HBr in glac. CH₃CO₂H) with preparation of nonmutagenic reaction mixtures of products;

DOI:10.1002/jps.2600780811

upstream raw materials:

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

4-methylcyclohexylamine

Downstream raw materials:

ethanol

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

ethylamine

4-methylcyclohexylamine

Refernces

• 1、 Johnston,McCaleb,Opliger,Montgomery. "The synthesis of potential anticancer agents. XXXVI. N-nitrosoureas. II. Haloalkyl derivatives.". . p. 892 - 911. Retrieved 2007/10/05.