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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB00773
rdf:type
n3:Drug
n3: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. [PubChem]
n3:dosage
n10:271B5DFE-363D-11E5-9242-09173F13E4C5 n10:271B5E01-363D-11E5-9242-09173F13E4C5 n10:271B5DFF-363D-11E5-9242-09173F13E4C5 n10:271B5E00-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Zhou Z, Zwelling LA, Ganapathi R, Kleinerman ES: Enhanced etoposide sensitivity following adenovirus-mediated human topoisomerase IIalpha gene transfer is independent of topoisomerase IIbeta. Br J Cancer. 2001 Sep 1;85(5):747-51. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11531262 # Azarova AM, Lyu YL, Lin CP, Tsai YC, Lau JY, Wang JC, Liu LF: Roles of DNA topoisomerase II isozymes in chemotherapy and secondary malignancies. Proc Natl Acad Sci U S A. 2007 Jun 26;104(26):11014-9. Epub 2007 Jun 19. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17578914
n3:group
approved
n3:halfLife
4-11 hours
n3: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.
n3:manufacturer
n13:271B5DF6-363D-11E5-9242-09173F13E4C5 n13:271B5DF1-363D-11E5-9242-09173F13E4C5 n13:271B5DED-363D-11E5-9242-09173F13E4C5 n13:271B5DF2-363D-11E5-9242-09173F13E4C5 n13:271B5DEE-363D-11E5-9242-09173F13E4C5 n13:271B5DEC-363D-11E5-9242-09173F13E4C5 n13:271B5DF4-363D-11E5-9242-09173F13E4C5 n13:271B5DF5-363D-11E5-9242-09173F13E4C5 n13:271B5DEF-363D-11E5-9242-09173F13E4C5 n13:271B5DF3-363D-11E5-9242-09173F13E4C5 n13:271B5DF0-363D-11E5-9242-09173F13E4C5
owl:sameAs
n15:DB00773 n30:DB00773
dcterms:title
Etoposide
adms:identifier
n6:Etoposide n7:0378-3266-94 n19:4911 n23:46505434 n24:C01576 n25:33510 n26:DB00773 n27:PA449552 n28:36462 n29:D00125
n3:mechanismOfAction
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.
n3:packager
n13:271B5DEB-363D-11E5-9242-09173F13E4C5 n13:271B5DE1-363D-11E5-9242-09173F13E4C5 n13:271B5DE2-363D-11E5-9242-09173F13E4C5 n13:271B5DDF-363D-11E5-9242-09173F13E4C5 n13:271B5DE0-363D-11E5-9242-09173F13E4C5 n13:271B5DDD-363D-11E5-9242-09173F13E4C5 n13:271B5DDE-363D-11E5-9242-09173F13E4C5 n13:271B5DDB-363D-11E5-9242-09173F13E4C5 n13:271B5DDC-363D-11E5-9242-09173F13E4C5 n13:271B5DE9-363D-11E5-9242-09173F13E4C5 n13:271B5DEA-363D-11E5-9242-09173F13E4C5 n13:271B5DE7-363D-11E5-9242-09173F13E4C5 n13:271B5DE8-363D-11E5-9242-09173F13E4C5 n13:271B5DE5-363D-11E5-9242-09173F13E4C5 n13:271B5DE6-363D-11E5-9242-09173F13E4C5 n13:271B5DE3-363D-11E5-9242-09173F13E4C5 n13:271B5DE4-363D-11E5-9242-09173F13E4C5
n3:routeOfElimination
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. 56% of the dose was in the urine, 45% of which was excreted as etoposide.
n3:synonym
Vepesid VP-16 Eposin 4-Demethylepipodophyllotoxin beta-D-ethylideneglucoside Lastet (-)-Etoposide Etoposide 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside) Etoposidum Epipodophyllotoxin Etoposido 9-((4,6-O-Ethylidine-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,4-dimethyloxyphenyl)furo(3',4'':6,7)naptho-(2,3-D)-1,3-dioxol-6(5ah)-one Etoposid EPEG EPE trans-Etoposide Toposar Etopophos
n3:toxicity
Side effects include alopecia, constipation, diarrhea, nausea and vomiting and secondary malignancies (leukemia).
n3:volumeOfDistribution
The disposition of etoposide is a biphasic process with a distribution half-life of 1.5 hours. It does not cross into cerebrospinal fluid well. Volume of distribution, steady state = 18 - 29 L.
n8:hasAHFSCode
n9:10-00-00
n3:foodInteraction
Grapefruit and grapefruit juice should be avoided throughout treatment as grapefruit can decrease serum levels of this product.
n3:proteinBinding
97% protein bound.
n3:salt
n3:synthesisReference
"DrugSyn.org":http://www.drugsyn.org/Etoposide.htm
n21:hasConcept
n22:M0007930
foaf:page
n12:etoposide.html n17:etopophos.htm
n3:IUPAC-Name
n4:271B5E06-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B5E0C-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B5E0B-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B5E08-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B5E09-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B5E0A-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B5E1C-363D-11E5-9242-09173F13E4C5 n4:271B5E04-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B5E1E-363D-11E5-9242-09173F13E4C5 n4:271B5E02-363D-11E5-9242-09173F13E4C5 n4:271B5E05-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B5E03-363D-11E5-9242-09173F13E4C5
n8:hasATCCode
n18:L01CB01
n3:H-Bond-Acceptor-Count
n4:271B5E12-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5E13-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B5E0D-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5E0E-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B5E10-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5E0F-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B5E11-363D-11E5-9242-09173F13E4C5
n3:absorption
Absorbed well, time to peak plasma concentration is 1-1.5 hrs. Mean bioavailability is 50% (range of 25% - 75%). Cmax and AUC values for orally administered etoposide capsules display intra- and inter-subject variability. There is no evidence of first-pass effect for etoposide.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
33419-42-0
n3:category
n3:clearance
* Total body clearance = 33 - 48 mL/min [IV administration, adults] * Mean renal clearance = 7 - 10 mL/min/m^2
n3:containedIn
n20:271B5DFD-363D-11E5-9242-09173F13E4C5 n20:271B5DFB-363D-11E5-9242-09173F13E4C5 n20:271B5DFC-363D-11E5-9242-09173F13E4C5 n20:271B5DF9-363D-11E5-9242-09173F13E4C5 n20:271B5DFA-363D-11E5-9242-09173F13E4C5 n20:271B5DF7-363D-11E5-9242-09173F13E4C5 n20:271B5DF8-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B5E18-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5E1A-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5E1B-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B5E1D-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B5E17-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B5E16-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B5E19-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B5E07-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B5E14-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B5E15-363D-11E5-9242-09173F13E4C5