2798. Dacarbazine

Nomenclature

CAS number: 4342-03-4
5-(3,3-Dimethyl-1-triazenyl)-1H-imidazole-4-carboxamide; 5(or 4)-(dimethyltriazeno)imidazole-4(or 5)-carboxamide; DIC; DTIC; NSC-45388; Dacatic (Orion); Dacin (Lipomed); DTIC-Dome (Bayer); Deticene (Sanofi-Aventis).
C6H10N6O; mol wt 182.18.
C 39.56%, H 5.53%, N 46.13%, O 8.78%.

Description and references

Alkylating agent; first synthesized in 1959 at the Southern Research Institute. Prepn: Y. F. Shealy et al., J. Org. Chem. 27, 2150 (1962); Hano et al., Gann 59, 207 (1968), C.A. 69, 42527g (1968). Antitumor activity: Shealy et al., Biochem. Pharmacol. 11, 674 (1962); Hano et al., Gann 56, 417 (1965), C.A. 63, 18856g (1965). Mechanism of action studies: Saunders, Schultz, Biochem. Pharmacol. 19, 911 (1970). Metabolism: Skibba et al., ibid. 2043; Mizuno, Humphrey, Cancer Chemother. Rep. Part 1 56, 465 (1972). Electroanalytical behavior: A. J. M. Ordieres et al., Anal. Chim. Acta 202, 141 (1987). Degradation in aqueous soln: B. V. Shetty et al., J. Pharm. Biomed. Anal. 10, 675 (1992). MS study of transition metal coordination: C. G. Hartinger et al., Polyhedron 25, 1971 (2006). Series of articles on history, activity, mechanism of action and clinical studies: Cancer Treat. Rep. 60, 123-214 (1976). Clinical evaluation in pancreatic islet cell cancer: R. K. Ramanathan et al., Ann. Oncol. 12, 1139 (2001). Review of clinical use in metastatic melanoma: A. M. M. Eggermont, J. M. Kirkwood, Eur. J. Cancer 40, 1825-1836 (2004).

Chemical structure

Properties

Ivory microcrystalline substance; explosive decomp 250-255° (Shealy, J. Org. Chem.). Also reported as mp 205° (Hano, 1965). uv max (0.1N HCl): 223 nm (7500); (pH 7): 237 nm (11200); both solns protected from light. Stable in neutral soln in absence of light.

Caution

This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-76.

Therapeutic Category

Antineoplastic.

Therapeutic Category (Veterinary)

Antineoplastic.

Keywords

Antineoplastic; Alkylating Agents