semustine

Description

semustine · CAS 13909-09-6 · C10H18ClN3O2. UNII 2281H4FBL9. Melting Point: 147 °F (NTP, 1992); Melting Point: 64 °C (decomposes); Solubility: Water 0.09 (mg/mL).

Identification

CAS Registry Number	13909-09-6
PubChem CID	5198
Molecular formula	C10H18ClN3O2
IUPAC name	1-(2-chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea
UNII (FDA)	2281H4FBL9

Computed Descriptors

Molecular Weight	247.72
XLogP3	3.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	247.1087545
Monoisotopic Mass	247.1087545
Topological Polar Surface Area	61.8
Heavy Atom Count	16
Formal Charge	0

Physical & Chemical Properties

Melting Point	147 °F (NTP, 1992)
Melting Point	64 °C (decomposes)
Solubility	Water 0.09 (mg/mL)
Solubility	0.1 N HCI 0.09 (mg/mL)
Solubility	0.1 N NaOH 0.09 (mg/mL)
Solubility	10% Ethanol 0.10 (mg/mL)
Solubility	DMSO 250.00 (mg/mL)
Solubility	Chloroform 667.00 (mg/mL)
LogP	log Kow = 3.30
LogP	3.25

Physical description & handling notes

• 1-(2-chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea is a light yellow powder. (NTP, 1992)
• Crystals
• less than 1 mg/mL at 64 °F (NTP, 1992)
• Absolute Ethanol 100.00 (mg/mL)
• It is stable under normal conditions but should be protected from moisture.
• Bulk: A sample stored at room temperature for 30 days showed 4% decomposition (UV). Solution: A refrigerated solution in 10% EtOH decomposed 2% in 6 hours while a solution at room temperature showed 25% decomposition in 6 hours (UV). Solutions in methanol were also found to be unstable by UV analysis.

GHS Hazard Classification

Reported hazard statements	H300 (100%), H311 (100%), H315 (100%), H319 (100%), H331 (100%), H335 (100%), H350 (100%), H360 (100%)

Documented Uses

• An antineoplastic agent which functions as an alkylating agent.
• Withdrawn as Investigational New Drug Application
• A methylated derivative of carmustine with antineoplastic activity.
• /EXPERIMENTAL THERAPY:/ Methyl-CCNU is an investigational drug used in chemotherapy to treat several types of cancers, including some brain cancers ... It also has been used to treat cancers of the lung and digestive tract.
• Dose-related nephrotoxicity subsequent to administration of certain chloroethylnitrosourea compounds (carmustine, semustine and streptozocin) is commonly heralded by increased serum creatinine levels, uremia and proteinuria .....
• A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA,

Synonyms

semustine; 13909-09-6; Methyl-CCNU; 1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea; Semustina; MeCCNU; METHYL CCNU; N-(2-Chloroethyl)-N'-(4-methylcyclohexyl)-N-nitrosourea; Semustinum; ICIG 1110; methyl lomustine; Lomustine, methyl; NSC 95441; Urea, N-(2-chloroethyl)-N'-(4-methylcyclohexyl)-N-nitroso-; NCI-C04955; DTXSID8031603

Frequently Asked Questions

What are the CAS number and molecular formula of semustine?

CAS 13909-09-6; molecular formula C10H18ClN3O2; molecular weight — g/mol.

What other names is semustine known by?

semustine, 13909-09-6, Methyl-CCNU, 1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea, Semustina, MeCCNU.

Is semustine classified as hazardous?

Hazard statements reported: H300, H311, H315, H319, H331.

What are the key physical properties of semustine?

Melting Point: 147 °F (NTP, 1992); Melting Point: 64 °C (decomposes); Solubility: Water 0.09 (mg/mL); Solubility: 0.1 N HCI 0.09 (mg/mL).

Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.