2996. Diaziquone

Nomenclature

CAS number: 57998-68-2
[2,5-Bis(1-aziridinyl)-3,6-dioxo-1,4-cyclohexadiene-1,4-diyl]biscarbamic acid diethyl ester; 2,5-bis(1-aziridinyl)-3,6-dioxo-1,4-cyclohexadiene-1,4-dicarbamic acid diethyl ester; 2,5-diaziridinyl-3,6-bis(ethoxycarbonylamino)-1,4-benzoquinone; aziridinylbenzoquinone; AZQ; CI-904; NSC-182986.
C16H20N4O6; mol wt 364.35.
C 52.74%, H 5.53%, N 15.38%, O 26.35%.

Description and references

Quinone-containing lipophilic alkylating agent. Prepn as intermediate in dyestuffs: S. Petersen et al., US 2913453 (1959 to Schenley Ind.). Synthesis and antitumor activity: A. H. Khan, J. S. Driscoll, J. Med. Chem. 19, 313 (1976); J. S. Driscoll et al., US 4146622 (1979 to U.S. Gov't). In vivo antitumor studies: J. S. Driscoll et al., J. Pharm. Sci. 68, 185 (1979). Intracerebral penetration and tissue distribution in humans: N. Savaraj et al., J. Neuro-Oncol. 1, 15 (1983). LC determn: B. A. Allen et al., J. Chromatogr. 222, 146 (1981). Pharmacokinetics: S. Zimm et al., Cancer Res. 44, 1698 (1984). Clinical studies in treatment of CNS neoplasms: R. T. Eagan et al., J. Neuro-Oncol. 5, 309 (1987); E. Tapazoglou et al., Am. J. Clin. Oncol. 11, 474 (1988). Review: J. F. Bender et al., Invest. New Drugs 1, 71-84 (1983).

Chemical structure

Properties

Orange needles from ethanol, mp 230° (dec); also reported as yellowish-brown crystals from ethanol decomposing at temperatures above 250° (Petersen). uv max (methanol): 340 nm (log ε 4.17). Soly in water: 0.5 mg/ml. LD50 in mice (mg/m2): 30.9 i.v. (Bender).

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Alkylating Agents; Aziridines