3912. Exatecan

Nomenclature

CAS number: 171335-80-1
(1S,9S)-1-Amino-9-ethyl-5-fluoro-1,2,3,9,12,15-hexahydro-9-hydroxy-4-methyl-10H,13H-benzo[de]pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-10,13-dione; DX-8951.
C24H22FN3O4; mol wt 435.45.
C 66.20%, H 5.09%, F 4.36%, N 9.65%, O 14.70%.

Description and references

Topoisomerase I inhibitor; synthetic analogue of camptothecin, q.v. Prepn: H. Terasawa et al., EP 495432 (1992 to Daiichi); of mesylate: S. Kamihara et al., EP 737686; eidem, US 6552197 (1996, 2003 both to Daiichi). HPLC determn in mouse plasma: T. Oguma et al., Biol. Pharm. Bull. 24, 176 (2001). Clinical pharmacokinetics and evaluation in advanced leukemia: F. J. Giles et al., Clin. Cancer Res. 8, 2134 (2002); in advanced solid malignancies: M. A. Garrison et al., ibid. 9, 2527 (2003); in breast cancer: F. J. Esteva et al., Cancer 98, 900 (2003); in gastric cancer: J. A. Ajani et al., Invest. New Drugs 23, 479 (2005).

Chemical structure

Derivative

Methanesulfonate dihydrate.

Nomenclature

CAS number: 197720-53-9; 169869-90-3 (anhydrous)
Exatecan mesylate; DX-8951f.
C24H22FN3O4.CH4O3S.2H2O; mol wt 567.58.
C 52.90%, H 5.33%, F 3.35%, N 7.40%, O 25.37%, S 5.65%.

Properties

mp 245-255° (dec). Sol in water.

Therapeutic Category

Antineoplastic.

Keywords

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