2177. Chlorozotocin

Nomenclature

CAS number: 54749-90-5
2-[[[(2-Chloroethyl)nitrosoamino]carbonyl]amino]-2-deoxy-d-glucose; 2-[3-(2-chloroethyl)-3-nitrosoureido]-2-deoxy-d-glucopyranose; 1-(2-chloroethyl)-1-nitroso-3-(d-glucos-2-yl)urea; DCNU; NSC-178248.
C9H16ClN3O7; mol wt 313.69.
C 34.46%, H 5.14%, Cl 11.30%, N 13.40%, O 35.70%.

Description and references

Chloroethylnitrosourea derivative with antitumor activity. Similar to carmustine, lomustine, nimustine, ranimustine, q.q.v; 2-chloroethyl analog of streptozotocin, q.v. Synthesis: H. D. Burns et al., Org. Prep. Proced. Int. 6, 259 (1974); T. P. Johnston et al., J. Med. Chem. 18, 104 (1975). Pharmacology: T. Anderson et al., Cancer Res. 35, 761 (1975); P. S. Schein et al., Cancer Treat. Rep. 60, 801 (1976). Decomposition in aqueous media: J. A. Montgomery et al., J. Med. Chem. 18, 568 (1975).

Chemical structure

Properties

Ivory colored crystals, mp 147-148° (dec with the evolution of gas), (Burns, Heindel). Also reported as mp 140-141° (dec), (Johnston). Sol in water.

Caution

This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-62.

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Alkylating Agents; Nitrosoureas