Etoposide

Topoisomerase Inhibitor

DB00773

Approved Indication

For use in combination with other chemotherapeutic agents in the treatment of refractory testicular tumors and as first line treatment in patients with small cell lung cancer. Also used to treat other malignancies such as lymphoma, non-lymphocytic leukemia, and glioblastoma multiforme.

2 Targets

0 Resistance Mutations

2 References

5GWK Structure Loaded

3D Structure PDB: 5GWK

Switch structure: RCSB ↗

Protein Targets

TOP2A P11388 ✓ 1 PDB TOP2B Q02880 1 PDB

Mechanism of Action

Etoposide inhibits DNA topoisomerase II, thereby inhibiting DNA re-ligation. This causes critical errors in DNA synthesis at the premitotic stage of cell division and can lead to apoptosis of the cancer cell. Etoposide is cell cycle dependent and phase specific, affecting mainly the S and G2 phases of cell division. Inhibition of the topoisomerase II alpha isoform results in the anti-tumour activity of etoposide. The drug is also capable of inhibiting the beta isoform but inhibition of this target is not associated with the anti-tumour activity. It is instead associated with the carcinogenic effect.

Details

DrugBank ID DB00773 ↗

Approval Date 1996-08-01

Molecular Weight 588.5566 g/mol

Drug Class Topoisomerase Inhibitor

ATC Codes L01CB01

Synonyms (−)-etoposide, Etoposido, Etoposidum

PubChem CID: 36462 ↗

ChEMBL CHEMBL44657 ↗

SMILES

[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])CO[C@@H](C)O[C@@]2([H])[C@H](O)[C@H]1O

ADMET Profile

Computing properties…

Drug References (DrugBank)

PMID:11531262 PMID:17578914