8288. Rubitecan

Nomenclature

CAS number: 91421-42-0
(4S)-4-Ethyl-4-hydroxy-10-nitro-1H-pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; 9-nitrocamptothecin; 9-nitro-(20S)-camptothecin; 9-NC; Orathecin (SuperGen).
C20H15N3O6; mol wt 393.35.
C 61.07%, H 3.84%, N 10.68%, O 24.40%.

Description and references

Semisynthetic camptothecin which inhibits DNA topoisomerase I. Prodrug of 9-aminocamptothecin, (9-AC), q.v. Prepn: JP Kokai 59 51288 (1984 to Yakult Honsha), C.A. 101, 91322 (1984); M. C. Wani et al., J. Med. Chem. 29, 2358 (1986); and activity: S. Sawada et al., Chem. Pharm. Bull. 39, 3183 (1991). Conversion to 9-AC by human cells: P. Pantazis et al., Eur. J. Haematol. 53, 246 (1994); eidem, ibid. 55, 211 (1995). Clinical trial in pancreatic cancer: J. S. Stehlin et al., Int. J. Oncol. 14, 821 (1999). Review of development and clinical experience: J. W. Clark, Expert Opin. Invest. Drugs 15, 71-79 (2006).

Chemical structure

Properties

Yellow amorphous powder from CH3OH-CHCl3 (13:87), mp 182-186°. [α]D23 +27° (c = 0.2 in CH3OH-CHCl3, 1:4).

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Alkaloids/Natural Products; Camptothecin Derivatives; Topoisomerase I Inhibitor