Cyclohexyl chloroethyl nitrosourea CCNU

Chloroethyl)-3-cyclohexyl-l-nitrosourea (CCNU) [13010-47-4] (Vol. 26, Suppl. 7 1 (NB Overall evaluation upgraded from 2B to 2A with supporting evidence from other carcinogenicity and its mechanisms)... 

Although N-methyl-N-nitrosourea can induce cancer in human beings, its derivatives were found to be potent antitumor agents. l,3-Bis(2-chloroethyl)-l-nitrosourea (BCNU), l-(2-chloroethyl)-3-cyclohexyl-l-nitrosourea (CCNU) and l-(2-chloroethyl)-3-(2,6-dioxo-3-piperidyl-l-nitrosourea (PCNU) l-(2-Choroethyl)-3-(4-methylcyclo-hexyl)-l-nitrosourea and l-(2-chloroethyl)-3-cyclohexyl-l-nitrosourea showed antitumor activity by alkylating with DNA [82-84]. N-Nitrosourea-based prodrugs designed to become activated by tumor-associated proteases were found to provide enhanced... 

Two TV-nitrosoureas, Bischloroethyl-nitrosourea (BCNU) and l-chloroethyl-3-cyclohexyl-1-nitrosourea (CCNU), have been used as anticancer agents in clinics but their mechanism and their toxicities have yet to be determined78. 

Chang, T.K..H., H. Chen, and D.J. Waxman (1994). l-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea (CCNU) modulates rat liver microsomal cyclophosphamide and ifosphamide activation by suppressing cytochrome P450 2C11 messenger RNA levels. Drug Metab. Dispos. 22,... 

Chloroethyl)-3-cyclohexyl-1 -nitrosourea CCNU Lomustine Belustine 13010-47-4... 

Twofold increases in SCE frequencies have been found in six patients treated with l-(2-chloroethyl)-3-cyclohexyl-l-nitrosourea (CCNU) and one patient treated with melphalan, although SCE frequencies in patients treated with fluorodeoxyuridine, vincristine, methotrexate, bleomycin, actinomycin D, adriamycin, and CP were all within the normal range.Increased SCEs have been found in cultured lymphocytes from individuals treated with adriamycin,and with CP alone or in combination with other cytostatic drugs. 

Nitrosoureas - 1,3-Bis (2-chloroethyl)-1-nitrosourea (BCNU), l-(2-chloroethyl)-3-cyclohexyl-l-nitrosourea (CCNU) are extremely lipid soluble and readily cross the blood-brain barrier.CCNU is more efficacious than BCNU against implanted gliomas and leukemia L-1210. Clinically,... 

Nitrosoureas such as 1,3-bls (2-chloroethyl)-1-nitrosourea (BCNU) and l-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea (CCNU) have shown significant activiiy in a wide spectrum of animal and human neoplasms 97-99 Qf particular value is their ability to penetrate the blood-brain barrier. These compounds appear to act by allqrlatlon of nucleic acids and/or by cyclohejqrlcarbamoylation of the lysine residues of proteins . 3-(Tetraacetyl glucopyranos-2-yl)-l-(2-chloroethyl)-l-nitrosourea (GCNU) (XI), which is structurally related to streptozotodn, is markedly active against leukemia L-1210, without the marked bone marrow toxicity exhibited by BCNU or CCNU . Marked inhibition of L-1210 growth has also been reported for 1,1 -ethylenebis (1-nitrosourea) and for the hexa-methylene derivative. ... 

SYNS BELUSTINE CCNU CECENU CEENU CHLOROETHYLCYCLOHEXYLNITROSOUREA N-(2-CHLOROETHYL)-N -CYCLOHEXYL-N-NITROSOUREA (CHLORO-2-ETHYL)-l-CYCLOHEXYL-3-NITROSOUREA CINU (CLORO-2-ETIL)-l-CICLOESIi 3-NITROSO-UREA (ITALIAN) ICIG 1109 LOMUSTINE NCI-C04740 NSC-79037 RB 1509 SRI 2200... 

SYNS N-(2-CHLOROETHYL)-N -(tratis-4-METHYL-CYCLOHEXYL)-N-NITROSOUREA l-(2-CHLORO-ETHYL)-3-(trans-4-METHYLCYCLOHEXYL)-l-NITROSOUREA ICIG 1110 ME-CCNU METHYL-CCNU trans-METHYL-CCNU METHYL-LOMUSTINE NCI-C04955 NSC-95441 SEMUSTINE... 

One further development is worth mentioning. A slight chemical modification to the nitrogen mustards provides the nitrosourea mustards like car-mustine (6zs-chloroethyl nitrosourea, BCNU), lomustine (chloroethyl, cyclohexyl nitrosourea, CCNU), semustine and streptozocin. The first three of these penetrate the brain well and are thus useful for eradicating deposits of cancer cells there. Unlike the other nitrosoureas, streptozocin is a natural product, isolated from the microorganism Streptomyces acromogenes, and has selectivity for tumours of the pancreas. 

The nitrosoureas, which include compounds, such as 1, 3- iT-(2-chloroethyl)-l-nitrosourea (carmustine BCNU), l-(2-chloroethyl)-3-cyclohexyl-l-nitrosourea (lomustine CCNU), and its methyl derivative (semustine methyl-CCNU), as well as the antibiotic streptozocin (streptozoto-cin), exert their cytotoxicity throngh the spontaneous breakdown to an alkylating intermediate, the 2-chloroethyl diazonium ion (see Fignre 15). 

METHYL CCNU (l-(2-CHLOROETHYL>3-(4-METHYL-CYCLOHEXYL-l-NITROSOUREA)... 

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