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| CAS No.: | 13010-47-4 |
|---|---|
| Name: | Lomustine |
| Molecular Structure: | |
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|
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| Formula: | C9H16ClN3O2 |
| Molecular Weight: | 233.698 |
| Synonyms: | CeeNU;Chloroethylcyclohexylnitrosourea;CiNu;ICIG 1109;Lomustin;N-(2-Chloroethyl)-N'-cyclohexyl-N-nitrosourea;NCI C04740;NSC 79037;RB 1509;SRI 2200;Urea,1-(2-chloroethyl)-3-cyclohexyl-1-nitroso- (7CI,8CI);1-(2-Chloroethyl)-1-nitroso-3-cyclohexylurea;1-(2-Chloroethyl)-3-cyclohexylnitrosourea;Belustine;CCNU;Cecenu; |
| EINECS: | 235-859-2 |
| Density: | 1.35 g/cm3 |
| Melting Point: | 88-90 °C |
| Boiling Point: | 296.6°C at 760 mmHg |
| Flash Point: | 133.2°C |
| Appearance: | Yellow powder |
| Hazard Symbols: |
 T
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| Risk Codes: | 45-25 |
| Safety: | 53-45 |
| PSA: | 61.77000 |
| LogP: | 2.64180 |
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- 73441-42-6METHYL-5-CHLORO-2,2-DIMETHYLVALERATE
- 13908-11-7
N-(2-chloroethyl)-N'-cyclohexylurea
- 13010-47-4
1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
| Conditions | Yield |
|---|---|
| With tin(IV) chloride; sodium nitrite In dichloromethane at 20℃; for 2h; | 100% |
| With tert.-butylnitrite In ethanol; acetonitrile at 25℃; for 0.133333h; Reagent/catalyst; Solvent; Temperature; Time; Flow reactor; | 91.2% |
| With tert.-butylnitrite In ethanol; acetonitrile at 25℃; for 0.133333h; Reagent/catalyst; Temperature; Solvent; | 91.2% |
- 80354-49-0
N-(2-chloroethyl)-N-nitrosocarbamic acid N-hydroxypyrrolidine-2,5-dione ester
- 108-91-8
cyclohexylamine
- 13010-47-4
1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
| Conditions | Yield |
|---|---|
| Ambient temperature; | 81% |
| In N,N-dimethyl-formamide at 0℃; for 2h; | 80% |
- 80354-51-4
(2-chloroethyl)nitrosocarbamic acid 2,4,5-trichlorophenyl ester
- 108-91-8
cyclohexylamine
- 13010-47-4
1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
| Conditions | Yield |
|---|---|
| In N,N-dimethyl-formamide at 0℃; for 2h; | 80% |
- 80354-53-6
N-(2-chloroethyl)-N-nitrosocarbamic acid pentachlorophenyl ester
- 108-91-8
cyclohexylamine
- 13010-47-4
1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
| Conditions | Yield |
|---|---|
| In N,N-dimethyl-formamide at 0℃; for 2h; | 80% |
- 108-91-8
cyclohexylamine
- 80354-55-8
pentafluorophenyl N-(2-chloroethyl)-N-nitrosocarbamate
- 13010-47-4
1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
| Conditions | Yield |
|---|---|
| In N,N-dimethyl-formamide at 0℃; for 2h; | 80% |
- 55661-43-3
p-nitrophenyl N-(2-chloroethyl)-N-nitroso-carbamate
- 108-91-8
cyclohexylamine
- 13010-47-4
1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
| Conditions | Yield |
|---|---|
| With pyridine; benzotriazol-1-ol 1.) -10 deg C, 1 h; 2.) 0 deg C, 24 h; | 75% |
- 1943-83-5
2-chloroethyl isothiocyanate
- 108-91-8
cyclohexylamine
- 13010-47-4
1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
| Conditions | Yield |
|---|---|
| Stage #1: 2-chloroethyl isothiocyanate; cyclohexylamine With triethylamine In tetrahydrofuran; dichloromethane at 50℃; for 0.0166667h; Stage #2: With tert.-butylnitrite In dichloromethane; acetonitrile at 25℃; for 0.133333h; Reagent/catalyst; Solvent; Temperature; | 63.7% |
- 76310-06-0
2-(cyclohexylimino)-3-nitroso-2-oxazolidine
- 13010-47-4
1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
| Conditions | Yield |
|---|---|
| With hydrogenchloride In diethyl ether at 0 - 4℃; for 0.5h; | 43% |
- 108-91-8
cyclohexylamine
- 113900-20-2
1,2,2,2-Tetrachloroethyl N-(2-chloroethyl) N-nitroso-carbamate
- 13010-47-4
1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
| Conditions | Yield |
|---|---|
| With potassium carbonate In tetrahydrofuran for 2h; Ambient temperature; Yield given; |
- 108-91-8
cyclohexylamine
- 13010-47-4
1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: H2O / Heating 2: 85percent formic acid, sodium nitrate / 0 °C View Scheme |
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Consensus Reports
Specification
The Lomustine is an organic compound with the formula C9H16ClN3O2. The IUPAC name of this chemical is 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea. With the CAS registry number 13010-47-4, it is also named as 1-Nitrosourea, 1-(2-chloroethyl)-3-cyclohexyl-. The product's categories are Pharmaceutical; Intermediates & Fine Chemicals; Nitric Oxide Reagents; Pharmaceuticals. Besides, it is a yellow powder, which should be stored in a closed cool and dry place at temperature of -20 °C.
The Lomustine is an alkylating nitrosourea compound used in chemotherapy. It is in the same family as streptozotocin. This is a highly lipid soluble drug, and thus crosses the blood brain barrier. This property makes it ideal for treating brain tumors, and is its primary use.
Physical properties about Lomustine are: (1)ACD/LogP: 2.76; (2)ACD/LogD (pH 5.5): 2.76; (3)ACD/LogD (pH 7.4): 2.76; (4)ACD/BCF (pH 5.5): 73.94; (5)ACD/BCF (pH 7.4): 73.91; (6)ACD/KOC (pH 5.5): 757.43; (7)ACD/KOC (pH 7.4): 757.19; (8)#H bond acceptors: 5; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 52.98 Å2; (12)Index of Refraction: 1.582; (13)Molar Refractivity: 57.84 cm3; (14)Molar Volume: 173 cm3; (15)Polarizability: 22.92×10-24cm3; (16)Surface Tension: 50.2 dyne/cm; (17)Density: 1.35 g/cm3.
Preparation: this chemical can be prepared by cyclohexyl-(3-nitroso-oxazolidin-2-ylidene)-amine. This reaction will need reagent HCl(g) and solvent diethyl ether. The reaction time is 30 min with reaction temperature of 0 - 4 °C. The yield is about 43%.
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When you are using this chemical, please be cautious about it as the following:
It is toxic if swallowed. Besides, this chemical may cause cancer. Please avoid exposure - obtain special instructions before use. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(NC1CCCCC1)N(N=O)CCCl
(2)InChI: InChI=1/C9H16ClN3O2/c10-6-7-13(12-15)9(14)11-8-4-2-1-3-5-8/h8H,1-7H2,(H,11,14)
(3)InChIKey: GQYIWUVLTXOXAJ-UHFFFAOYAV
(4)Std. InChI: InChI=1S/C9H16ClN3O2/c10-6-7-13(12-15)9(14)11-8-4-2-1-3-5-8/h8H,1-7H2,(H,11,14)
(5)Std. InChIKey: GQYIWUVLTXOXAJ-UHFFFAOYSA-N
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LDLo | intravenous | 5mg/kg (5mg/kg) | Cancer Chemotherapy Reports, Part 3. Vol. 4(3), Pg. 13, 1973. | |
| dog | LDLo | oral | 10mg/kg (10mg/kg) | Advances in Cancer Research. Vol. 16, Pg. 273, 1972. | |
| human | TDLo | oral | 3mg/kg (3mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING BLOOD: LEUKOPENIA BLOOD: THROMBOCYTOPENIA | Cancer Treatment Reports. Vol. 60, Pg. 709, 1976. |
| human | TDLo | oral | 30mg/kg (30mg/kg) | BEHAVIORAL: ANOREXIA (HUMAN GASTROINTESTINAL: NAUSEA OR VOMITING | Cancer Chemotherapy Reports, Part 3. Vol. 3, Pg. 33, 1972. |
| monkey | LDLo | intravenous | 20mg/kg (20mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA | National Technical Information Service. Vol. PB214-246, |
| mouse | LD10 | intravenous | 40mg/kg (40mg/kg) | Antibiotics and Chemotherapy Vol. 23, Pg. 64, 1978. | |
| mouse | LD50 | intraperitoneal | 53mg/kg (53mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED | Toxicology and Applied Pharmacology. Vol. 21, Pg. 405, 1972. |
| mouse | LD50 | oral | 38mg/kg (38mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" | Toxicology and Applied Pharmacology. Vol. 21, Pg. 405, 1972. |
| mouse | LD50 | subcutaneous | 54mg/kg (54mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED | Toxicology and Applied Pharmacology. Vol. 21, Pg. 405, 1972. |
| mouse | LD50 | unreported | 30mg/kg (30mg/kg) | European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 12, Pg. 397, 1977. | |
| rat | LD50 | intraperitoneal | 50350ug/kg (50.35mg/kg) | National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986, | |
| rat | LD50 | oral | 70mg/kg (70mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" | Toxicology and Applied Pharmacology. Vol. 21, Pg. 405, 1972. |
| women | LDLo | oral | 28mg/kg/1W-I (28mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BLOOD: APLASTIC ANEMIA | Annals of Pharmacotherpy. Vol. 29, Pg. 384, 1995. |