- Molecular NameEtoposide
- Synonym(-)-Etoposide; Etoposidum [INN-Latin]; trans-Etoposide
- Weight588.562
- Drugbank_IDDB00773
- ACS_NO33419-42-0
- Show 2D model
- LogP (experiment)0.6
- LogP (predicted, AB/LogP v2.0)0.54
- pka9.7
- LogD (pH=7, predicted)0.54
- Solubility (experiment)0.1 mg/ml
- LogS (predicted, ACD/Labs)(ph=7)-3.88
- LogSw (predicted, AB/LogsW2.0)0.76
- Sw (mg/ml) (predicted, ACD/Labs)0.08
- No.of HBond Donors3
- No.of HBond Acceptors13
- No.of Rotatable Bonds5
- TPSA160.83
- StatusFDA approved
- AdministrationN/A
- PharmacologyAn inhibitor of the enzyme topoisomerase II. It is used as a form of chemotherapy for malignancies such as Ewing's sarcoma, lung cancer, testicular cancer, lymphoma, non-lymphocytic leukemia, and glioblastoma multiforme. It is often given in combination with other drugs. It is also sometimes used in a conditioning regimen prior to a bone marrow or blood stem cell transplant.
- Absorption_value50.0
- Absorption (description)Pharmacokinetics show wide interindividual variation. Absorption is variable after oral administration, but on average about 50% of a dose is absorbed. Peak plasma concentrations occur 0.5 to 3 h after oral administration. A substrate for P-glycoprotein
- Caco_2N/A
- Bioavailability52.0
- Protein binding96.0
- Volume of distribution (VD)0.36 L/kg
- Blood/Plasma Partitioning ratio (D_blood)N/A
- MetabollsmUndergoes rapid distribution (CYP3A). It is metabolised to several metabolites, including a hydroxy acid metabolite, glucuronide and sulfate conjugates, and an O-demethylated compound.
- Half life8.1 h
- ExcretionExcreted in urine and via bile in the faeces (a small amount) as unchanged drug and metabolites; 30 to 50% of a dose is excreted in urine over 72 h as the unchanged drug and 20% as metabolites. Crosses the blood–brain barrier poorly; concentrations in CSF about 1 to 10% of those in plasma. It is distributed into breast milk.
- Urinary Excretion35
- Clerance0.68 ml/min/kg
- ToxicitySide effects include alopecia, constipation, diarrhea, nausea and vomiting and secondary malignancies (leukemia). Etoposide doses of 2.4 to 3.5 mg/m2 administered intravenously over 3 days caused severe mucositis and myelotoxicity. Metabolic acidosis and cases of severe hepatotoxicity have also been reported with doses above the recommended [Bristol Myers Squibb Pharmaceuticals Ltd., prescribing data]. The dose-limiting toxicity is dose-related myelosuppression.
- LD50 (rat)N/A
- LD50 (mouse)N/A