9145. Teniposide

Nomenclature

CAS number: 29767-20-2
(5R,5aR,8aR,9S)-5,8,8a,9-Tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[[4,6-O-[(R)-2-thienylmethylene]-β-d-glucopyranosyl]oxy]furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; 4′-demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-β-d-glucopyranoside); 4′-demethylepipodophyllotoxin-β-d-thenylidine glucoside; ETP; NSC-122819; VM-26; Vehem-Sandoz (Sandoz); Vumon (BMS).
C32H32O13S; mol wt 656.65.
C 58.53%, H 4.91%, O 31.67%, S 4.88%.

Description and references

Semi-synthetic derivative of podophyllotoxin, q.v. Prepn: A. Von Wartburg, ZA 6607585; C. Keeler-Juslen et al., US 3524844 (1968, 1970 both to Sandoz). Mechanism of action: H. St"ahlen, Eur. J. Cancer 6, 303 (1970). Pharmacology: M. Hacker, D. Roberts, Cancer Res. 37, 3287 (1977); S. M. Sieber et al., Teratology 18, 31 (1978); T. J. Vietti et al., Cancer Treat. Rep. 62, 1313 (1978). Metabolism: L. Allen, Drug Metab. Rev. 8, 119 (1978); Cancer Res. 38, 2549 (1978). Clinical studies: N. M. Gadel-Mawla et al., Cancer Treat. Rep. 62, 993 (1978); R. E. Bellet et al., ibid. 445. Studies on delayed toxicity in mice after i.p. injections: M. Hacker, D. Roberts, Cancer Res. 35, 1756 (1975); H. St"ahlin, Eur. J. Cancer 12, 925 (1976). Review of pharmacology, pharmacokinetics and assay methods: P. I. Clark, M. L. Slevin, Clin. Pharmacokinet. 12, 223-252 (1987). Comprehensive description: J. J. Kettenes-van den Bosch et al., Anal. Profiles Drug Subs. 19, 575-600 (1990).

Chemical structure

Properties

Crystals from abs ethanol, mp 242-246°. [α]D20 -107° (9:1 chloroform/methanol). uv max (methanol): 283 nm (E1%1cm 64.1). pKa 10.13.

Therapeutic Category

Antineoplastic.

Keywords

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