593. Amrubicin

Nomenclature

CAS number: 110267-81-7
(7S,9S)-9-Acetyl-9-amino-7-[(2-deoxy-β-d-erythro-pentopyranosyl)oxy]-7,8,9,10-tetrahydro-6,11-dihydroxy-5,12-naphthacenedione; (+)-9-amino-4-demethoxy-9-deoxy-7-O-(2-deoxy-β-d-erythro-pentopyranosyl)daunomycinone.
C25H25NO9; mol wt 483.47.
C 62.11%, H 5.21%, N 2.90%, O 29.78%.

Description and references

Synthetic anthracycline antibiotic; inhibits DNA topoisomerase II. Prepn: K. Ishizumi et al., EP 107486; eidem, US 4673668 (1984, 1987 both to Sumitomo); eidem, J. Org. Chem. 52, 4477 (1987). NMR study of complex with DNA: J. Igarashi, M. Sunagawa, Bioorg. Med. Chem. Lett. 5, 2923 (1995). Mechanism of action: M. Hanada et al., Jpn. J. Cancer Res. 89, 1229 (1998). Toxicology: S. Morisada et al., ibid. 80, 77 (1989). Clinical pharmacokinetics: K. Inoue et al., Invest. New Drugs 7, 213 (1989); Y. Matsunaga et al., Ther. Drug Monit. 28, 76 (2006). Clinical evaluation in lung cancer: T. Sugiura et al., Invest. New Drugs 23, 331 (2005); in combination with cisplatin: Y. Ohe et al., Ann. Oncol. 16, 430 (2005).

Chemical structure

Properties

mp 172-174°. [α]D20 +119° (c = 0.02 in CHCl3).

Derivative

Hydrochloride.

Nomenclature

CAS number: 110311-30-3
SM-5887; Calsed (Sumitomo).
C25H25NO9.HCl; mol wt 519.93.
C 57.75%, H 5.04%, N 2.69%, O 27.69%, Cl 6.82%.

Properties

mp 145-151°. LD50 i.v. in mice: 32-50 mg/kg (Morisada).

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Antibiotics and Analogs; Anthracyclines; Topoisomerase II Inhibitor