teniposide   Click here for help

GtoPdb Ligand ID: 6843

Synonyms: isosulfan blue | VM-26 | Vumon®
Approved drug PDB Ligand
teniposide is an approved drug (FDA (1992))
Compound class: Synthetic organic
Comment: A podophyllotoxin derivative which achieves cytotoxicity by inhibiting type II topoisomerase activity. Many (85) isomeric alternatives for this compound are listed on PubChem. Click here to link directly to the PubChem listing. The structure shown here matches that shown in the INN document for this compound.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 189.07
Molecular weight 656.16
XLogP 1.19
No. Lipinski's rules broken 0
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Canonical SMILES COc1cc(cc(c1O)OC)C1C2C(=O)OCC2C(c2c1cc1OCOc1c2)OC1OC2COC(OC2C(C1O)O)c1cccs1
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)c1cccs1
InChI InChI=1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31+,32-/m0/s1
No information available.
Summary of Clinical Use Click here for help
Used to treat refractory acute lymphoblastic leukemia, predominantly in children.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
A semisynthetic derivative of podophyllotoxin that exhibits antitumor activity. Forms a complex with topoisomerase II and DNA thereby inhibiting DNA synthesis and leading to cell death by preventing cells form undergoing mitosis.
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