9139. Temozolomide

Nomenclature

CAS number: 85622-93-1
3,4-Dihydro-3-methyl-4-oxoimidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxamide; 8-carbamoyl-3-methylimidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one; methazolastone; M & B 39831; CCRG-81045; NSC-362856; Temodal (Schering-Plough); Temodar (Schering-Plough).
C6H6N6O2; mol wt 194.15.
C 37.12%, H 3.11%, N 43.29%, O 16.48%.

Description and references

Imidazotetrazine alkylating agent. Prepn: E. Lunt et al., DE 3231255 (1983 to May & Baker); eidem, US 5260921 (1993 to Cancer Res. Campaign Technol.); M. F. G. Stevens et al., J. Med. Chem. 27, 196 (1984). Crystal structure and structure-activity study: P. R. Lowe et al., ibid. 35, 3377 (1992). Synthesis: Y. Wang et al., J. Org. Chem. 62, 7288 (1997). HPLC determn in plasma and urine: F. Shen et al., J. Chromatogr. B 667, 291 (1995). Review of pharmacology and clinical efficacy in melanoma and brain tumor: E. S. Newlands et al., Cancer Treat. Rev. 23, 35-61 (1997); S. J. Danson, M. R. Middleton, Expert Rev. Anticancer Ther. 1, 13-19 (2001).

Chemical structure

Properties

Crystals from dichloromethane, mp 212° (dec). uv max (95% ethanol): 327 nm.

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Alkylating Agents