etoposide   Click here for help

GtoPdb Ligand ID: 6815

Synonyms: (-)-etoposide | Etopophos® | Toposar® | trans-etoposide | VePesid® | VP 16-213 | VP-16
Approved drug PDB Ligand
etoposide is an approved drug (FDA (1983))
Compound class: Synthetic organic
Comment: A DNA topoisomerase II inhibitor which is a synthetic derivative of podophyllotoxin, found in the American Mayapple (Podophyllum peltatum).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 160.83
Molecular weight 588.18
XLogP 0.78
No. Lipinski's rules broken 0
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Canonical SMILES COc1cc(cc(c1O)OC)C1C2C(=O)OCC2C(c2c1cc1OCOc1c2)OC1OC2COC(OC2C(C1O)O)C
Isomeric SMILES COc1cc(cc(c1O)OC)[C@H]1[C@H]2C(=O)OC[C@@H]2[C@@H](c2c1cc1OCOc1c2)O[C@@H]1O[C@@H]2CO[C@H](O[C@H]2[C@@H]([C@H]1O)O)C
InChI InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1
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Summary of Clinical Use Click here for help
This compund is a topoisomerase inhibitor used as an anticancer agent, for cancers such as Kaposi's sarcoma, Ewing's sarcoma, lung cancer, testicular cancer, lymphoma, nonlymphocytic leukemia, and glioblastoma multiforme. It is often given in combination with other drugs (such as bleomycin in treating testicular cancer). It is also sometimes used in a conditioning regimen prior to a bone marrow or blood stem cell transplant
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Inhibits DNA synthesis by forming a complex with topoisomerase II and DNA, leading to the accumulation of DNA breaks which prevent the cell from entering mitotic cell division and subsequent cell death.
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