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Substance Name: Semustine [USAN:INN]
RN: 13909-09-6
UNII: 6YY7T1T567
InChIKey: FVLVBPDQNARYJU-UHFFFAOYSA-N

Note

  • 4-Methyl derivative of LOMUSTINE; (CCNU). An antineoplastic agent which functions as an alkylating agent.

Molecular Formula

  • C10-H18-Cl-N3-O2

Molecular Weight

  • 247.7242
 

Classification Codes

Classification Codes

  • Alkylating Agents
  • Antineoplastic
  • Antineoplastic Agents
  • Antineoplastic Agents, Alkylating
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Noxae
  • Skin / Eye Irritant
  • Tumor Data

Superlist Classification Codes

  • Known to be a Carcinogen
  • Overall Carcinogenic Evaluation: Group 1
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Names and Synonyms

Name of Substance

  • Semustine
  • Semustine [USAN:INN]

MeSH Heading

  • Semustine

Synonyms

  • 1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea
  • CCRIS 6336
  • HSDB 7760
  • ICIG 1110
  • Lomustine, methyl-
  • Methyl-CCNU
  • N-(2-Chloroethyl)-N'-(trans-4-methylcyclohexyl)-N-nitrosourea
  • NCI-C04955
  • NSC 95441
  • Semustina
  • Semustina [INN-Spanish]
  • Semustine
  • Semustinum
  • Semustinum [INN-Latin]
  • UNII-6YY7T1T567
  • Urea, 1-(2-chloroethyl)-3-(4-methylcyclohexyl)-1-nitroso-, trans-

Systematic Names

  • N-(2-Chloroethyl)-N'-(4-methylcyclohexyl)-N-nitrosourea
  • Urea, 1-(2-chloroethyl)-3-(4-methylcyclohexyl)-1-nitroso-
  • Urea, N-(2-chloroethyl)-N'-(4-methylcyclohexyl)-N-nitroso-

Superlist Names

  • 1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea
  • 1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea [Chloroethyl nitrosoureas]
  • MeCCNU
  • Methyl-CCNU
  • Methyl-CCNU [Chloroethyl nitrosoureas]

Registry Numbers

CAS Registry Number

  • 13909-09-6

FDA UNII

  • 6YY7T1T567

Other Registry Number

  • 56748-54-0

System Generated Number

  • 0013909096

Structure Descriptors

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)

InChIKey

FVLVBPDQNARYJU-UHFFFAOYSA-N

Smiles

C1(NC(N(CCCl)N=O)=O)CCC(C)CC1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
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.
child TDLo oral 37950mg/kg/2Y (37950mg/kg) KIDNEY, URETER, AND BLADDER: CHANGES IN BOTH TUBULES AND GLOMERULI New England Journal of Medicine. Vol. 300, Pg. 1200, 1979.
dog LDLo intravenous 14mg/kg (14mg/kg) BLOOD: AGRANULOCYTOSIS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Cancer Treatment Reports. Vol. 60, Pg. 1559, 1976.
dog LDLo oral 25mg/kg (25mg/kg)   Advances in Cancer Research. Vol. 16, Pg. 273, 1972.
human TDLo oral 6mg/kg (6mg/kg) BLOOD: THROMBOCYTOPENIA

BLOOD: LEUKOPENIA

GASTROINTESTINAL: NAUSEA OR VOMITING
Cancer Treatment Reports. Vol. 60, Pg. 709, 1976.
human TDLo oral 90mg/kg (90mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: LEUKOPENIA

BLOOD: THROMBOCYTOPENIA
Cancer Chemotherapy Reports, Part 3. Vol. 4, Pg. 257, 1973.
monkey LDLo intravenous 45mg/kg (45mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE

BLOOD: OTHER CHANGES
Cancer Treatment Reports. Vol. 60, Pg. 1559, 1976.
monkey LDLo oral 100mg/kg (100mg/kg)   Cancer Chemotherapy Reports, Part 3. Vol. 4(3), Pg. 13, 1973.
mouse LD10 intraperitoneal 37mg/kg (37mg/kg)   Cancer Research. Vol. 34, Pg. 194, 1974.
mouse LD50 oral 49900ug/kg (49.9mg/kg) BEHAVIORAL: WITHDRAWAL

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
National Technical Information Service. Vol. PB269-473,
mouse LD50 unreported 30mg/kg (30mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 12, Pg. 397, 1977.
rat LDLo subcutaneous 100mg/kg (100mg/kg)   Toxicology and Applied Pharmacology. Vol. 82, Pg. 540, 1986.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 3.3 (none)   EXP
Water Solubility 37 mg/L 25 EST
Vapor Pressure 5.61E-06 mm Hg 25 EST
Henry's Law Constant 2.46E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.36E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.