3886. Etoposide

Nomenclature

CAS number: 33419-42-0
9-[(4,6-O-Ethylidene-β-d-glucopyranosyl)oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; 4′-demethylepipodophyllotoxin 9-[4,6-O-ethylidene-β-d-glucopyranoside]; EPEG; NSC-141540; VP-16-213; Lastet (Nippon Kayaku); Vepesid (BMS).
C29H32O13; mol wt 588.56.
C 59.18%, H 5.48%, O 35.34%.

Description and references

DNA topoisomerase II inhibitor. Semi-synthetic deriv of podophyllotoxin, related structurally to teniposide, q.q.v. Prepn: C. Keller-Juslén et al., US 3524844 (1970 to Sandoz); idem et al., J. Med. Chem. 14, 936 (1971). Teratogenicity and cytogenicity study: S. M. Sieber et al., Teratology 18, 31 (1978). Review of pharmacokinetics and assay methods: P. I. Clark, M. L. Slevin, Clin. Pharmacokinet. 12, 223-252 (1987). Comprehensive description: J. J. M. Holthuis et al., Anal. Profiles Drug Subs. 18, 121-151 (1989). Review of pharmacology and clinical experience: J. D. Hainsworth, F. A. Greco, Ann. Oncol. 6, 325-341 (1995); S. Joel, Cancer Treat. Rev. 22, 179-221 (1996).

Chemical structure

Properties

Crystals from methanol, mp 236-251°. [α]D20 -110.5° (c = 0.6 in chloroform). uv max (abs methanol): 283 nm (ε 4245). pKa 9.8. Very sol in methanol, chloroform; slightly sol in ethanol; sparingly sol in water.

Derivative

Phosphate.

Nomenclature

CAS number: 117091-64-2
BMY-40481; Etopophos (BMS).
C29H33O16P; mol wt 668.54.
C 52.10%, H 4.98%, O 38.29%, P 4.63%.

Description and references

Review: A. H. I. Witterland et al., Pharm. World Sci. 18, 163-170 (1996).

Properties

Sol in water. Practically insol in organic solvents.

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Alkaloids/Natural Products; Podophyllum Derivatives; Topoisomerase II Inhibitor