3512. Edotecarin

Nomenclature

CAS number: 174402-32-5
12-β-d-Glucopyranosyl-12,13-dihydro-2,10-dihydroxy-6-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione; ED-749; J-107088; PF-804950; PHA-782615.
C29H28N4O11; mol wt 608.55.
C 57.24%, H 4.64%, N 9.21%, O 28.92%.

Description and references

Topoisomerase I inhibitor that induces single strand DNA cleavage. Prepn: K. Kojiri et al., EP 760375; eidem, US 5922860 (1997, 1999 both to Banyu Pharm.); M. Ohkubo et al., Bioorg. Med. Chem. Lett. 9, 3307 (1999). Synthesis: A. Akao et al., Tetrahedron 57, 8917 (2001). Mechanism of action study: T. Yoshinari et al., Cancer Res. 59, 4271 (1999). In vivo antitumor activity: H. Arakawa et al., Jpn. J. Cancer Res. 90, 1163 (1999). LC/MS/MS determn in plasma: A. Q. Wang et al., Rapid Commun. Mass Spectrom. 16, 975 (2002). Review of development: W. A. Denny, IDrugs 7, 173-177 (2004); and clinical experience: M. W. Saif, R. B. Diasio, Clin. Colorectal Cancer 5, 27-36 (2005).

Chemical structure

Properties

Orange solid, mp 330° (dec). [α]D23 +117° (c = 0.8 in 1:1 acetonitrile/water).

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Topoisomerase I Inhibitor