6217. Mitoxantrone

Nomenclature

CAS number: 65271-80-9
1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione; DHAQ; NSC-279836.
C22H28N4O6; mol wt 444.48.
C 59.45%, H 6.35%, N 12.61%, O 21.60%.

Description and references

Immunosuppressive and cytostatic anthracenedione. Prepn: R. K. Y. Zee-Cheng, C. C. Cheng, J. Med. Chem. 21, 291 (1978); K. C. Murdock et al., ibid. 22, 1024 (1979); eidem, DE 2835661; K. C. Murdock, F. E. Durr, US 4197249 (1979, 1980 both to Am. Cyanamid). Antitumor activity: R. E. Wallace et al., Cancer Res. 39, 1570 (1979). HPLC determn in plasma: K. T. Lin et al., J. Chromatogr. 465, 75 (1989). Clinical evaluation in indolent lymphomas: F. Hagemeister et al., Oncologist 10, 150 (2005); in neuromyelitis optica: B. Weinstock-Guttman et al., Arch. Neurol. 63, 957 (2006). Comprehensive description: J. H. Beijnen et al., Anal. Profiles Drug Subs. 17, 221-258 (1988). Review of toxicology: M. McDonald et al., Drugs Exp. Clin. Res. 10, 745-752 (1984); of pharmacology and clinical efficacy in cancer: J. Koeller, M. Eble, Clin. Pharm. 7, 574-581 (1988); of pharmacokinetics and metabolism: G. Ehninger et al., Clin. Pharmacokinet. 18, 365-380 (1990); of pharmacology and clinical efficacy in multiple sclerosis: E. J. Fox, Clin. Ther. 28, 461-474 (2006); O. Neuhaus et al., Pharmacol. Ther. 109, 198-209 (2006).

Chemical structure

Properties

Crystals from ethanol/hexane, mp 160-162°. Abs max (ethanol): 244, 279, 525, 620, 660 nm (log ε 4.64, 4.31, 3.70, 4.37, 4.38). Sparingly sol in water, slightly sol in methanol. Practically insol in acetonitrile, chloroform, acetone.

Derivative

Dihydrochloride.

Nomenclature

CAS number: 70476-82-3
DHAD; CL-232315; NSC-301739; Elsep (Wyeth); Novantron (Wyeth); Novantrone (Immunex); Onkotrone (Baxter); Ralenova (Wyeth).
C22H28N4O6.2HCl; mol wt 517.40.
C 51.07%, H 5.84%, N 10.83%, O 18.55%, Cl 13.70%.

Properties

Hygroscopic blue-black solid from water/ethanol, mp 203-205°. Abs max (water): 241, 273, 608, 658 nm (ε 41000, 12000, 19200, 20900). Sparingly sol in water, slightly sol in methanol. Practically insol in acetonitrile, chloroform, acetone.

Therapeutic Category

Antineoplastic; immunomodulator.

Therapeutic Category (Veterinary)

Antineoplastic.

Keywords

Antineoplastic; Immunomodulator; Topoisomerase II Inhibitor