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PubChem
Name: Etoposide
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
DrugBank
Identification
Name: Etoposide
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
Brand: Etopophos, Zuyeyidal, Vepesid J, Toposar, Eposin, Vepesid, Lastet
Category: Antineoplastic Agents, Phytogenic, Nucleic Acid Synthesis Inhibitors
CAS number: 33419-42-0
Pharmacology
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.
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
Interactions
Food interaction:
Grapefruit and grapefruit juice should be avoided throughout treatment as grapefruit can decrease serum levels of this product.
Drug interaction:
TelithromycinTelithromycin may reduce clearance of Etoposide. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Etoposide if Telithromycin is initiated, discontinued or dose changed.
TrastuzumabTrastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
CyclosporineCyclosporine may increase the therapeutic and adverse effects of etoposide.
VoriconazoleVoriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of etoposide by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of etoposide if voriconazole is initiated, discontinued or dose changed.
QuinupristinThis combination presents an increased risk of toxicity
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