1244. Bisantrene

Nomenclature

CAS number: 78186-34-2
9,10-Anthracenedicarboxaldehyde bis[(4,5-dihydro-1H-imidazol-2-yl)hydrazone]; 9,10-anthracenedicarboxaldehyde bis(2-imidazolin-2-ylhydrazone).
C22H22N8; mol wt 398.46.
C 66.31%, H 5.57%, N 28.12%.

Description and references

Prepn: K. C. Murdock et al., DE 2850822; K. C. Murdock, F. E. Durr, US 4258181 (1979, 1981 both to Am. Cyanamid); and antitumor activity: K. C. Murdock et al., J. Med. Chem. 25, 505 (1982). Crystallographic characterization of hydrochloride: R. B. Bates et al., Acta Crystallogr. C42, 186 (1986); C. G. Pierpont, S. A. Lang, Jr., ibid. 1085. HPLC determn in plasma: Y.-M. Peng et al., J. Chromatogr. 233, 235 (1982). Antitumor activity in vitro: J. D. Cowan et al., Invest. New Drugs 1, 139 (1983); in vivo: R. V. Citarella et al., Cancer Res. 42, 440 (1982). Clinical pharmacokinetics: K. Lu et al., Cancer Chemother. Pharmacol. 16, 156 (1986). Clinical trials in breast cancer: H.-Y. Yap et al., Cancer Res. 43, 1402 (1983); C. K. Osborne et al., Cancer Treat. Rep. 68, 357 (1984).

Chemical structure

Derivative

Dihydrochloride.

Nomenclature

CAS number: 71439-68-4
ADAH; ADCA; NSC-337766; CL-216942; Orange Crush (Cyanamid); Zantrène (Lederle).
C22H22N8.2HCl; mol wt 471.39.
C 56.05%, H 5.13%, N 23.77%, Cl 15.04%.

Properties

Crystalline orange solid from ethanol. Hemihydrate, mp 288-289° (dec). uv max (H2O) 260, 415 nm (ε 72700, 16300).

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic