Name: | Etoposide |
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PubChem Compound ID: | 11870245 |
Description: | A semisynthetic derivative of PODOPHYLLOTOXIN that exhibits antitumor activity. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle. |
Molecular formula: | C29H32O13 |
Molecular weight: | 588.557 g/mol |
Synonyms: |
ZINC03925951; 33419-42-0
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Name: | Etoposide |
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Name (isomeric): | DB00773 |
Drug Type: | small molecule |
Description: | A semisynthetic derivative of PODOPHYLLOTOXIN that exhibits antitumor activity. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle. |
Synonyms: |
Etoposidum [INN-Latin]; (-)-Etoposide; trans-Etoposide
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Brand: | Etopophos, Zuyeyidal, Vepesid J, Toposar, Eposin, Vepesid, Lastet |
Category: | Antineoplastic Agents, Phytogenic, Nucleic Acid Synthesis Inhibitors |
CAS number: | 33419-42-0 |
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. |
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Pharmacology: |
Etoposide is an antineoplastic agent and an epipodophyllotoxin (a semisynthetic derivative of the podophyllotoxins). It inhibits DNA topoisomerase II, thereby ultimately inhibiting DNA synthesis. Etoposide is cell cycle dependent and phase specific, affecting mainly the S and G2 phases. Two different dose-dependent responses are seen. At high conce...
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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. |
Absorption: | Absorbed well, time to peak plasma concentration is 1-1.5 hrs. Mean bioavailability is 50%. |
Protein binding: | 97% |
Biotransformation: | Primarily hepatic (through O-demethylation via the CYP450 3A4 isoenzyme pathway) with 40% excreted unchanged in the urine. |
Route of elimination: | Etoposide is cleared by both renal and nonrenal processes, i.e., metabolism and biliary excretion. Glucuronide and/or sulfate conjugates of etoposide are also excreted in human urine. Biliary excretion of unchanged drug and/or metabolites is an important route of etoposide elimination as fecal recovery of radioactivity is 44% of the intravenous dose. Only 8% or less of an intravenous dose is excreted in the urine as radiolabeled metabolites of 14C-etoposide. |
Half Life: | 4-12 hours |
Clearance: | 33 - 48 mL/min [IV administration] |
Toxicity: | Side effects include alopecia, constipation, diarrhea, nausea and vomiting and secondary malignancies (leukemia). |
Affected organisms: | Humans and other mammals |
Food interaction: |
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