Etoposide (CED0001059)

Record Information
Version1.0
Creation Date2014-09-11 02:05:21 UTC
Update Date2026-05-14 16:48:29 UTC
SynCED IDCED0001059
Secondary Accession Numbers
  • CHEM003653
  • T3D4695
Identification
Common NameEtoposide
ClassSmall Molecule
Description
Etoposide belongs to the podophyllotoxins, a subclass of lignan lactones within the organic compounds. With an average molecular weight of 588.56 g/mol, Etoposide is a heavy molecule. This exogenous solid has the chemical formula C29H32O13. It is used as a treatment for cancer (PMC12993860 , PMC5564849 ), leukemia (PMC4558124 ), breast cancer (PMC11084730 ), prostate cancer (PMC13031462 ), pain (PMC4718299 ), and fever (PMC4718299 ). Its recorded protein targets include DNA topoisomerase 2-alpha (TOP2A) and DNA topoisomerase 2-beta (TOP2B). Etoposide is found in or released from eight recorded sources, including healthcare, pharmaceuticals & veterinary products (antineoplastic agents), food, food processing & cookware (processing meats), household cleaning & consumer products (soap dispensers), and electrical & electronic equipment (antennas, electric switches, emergency protective devices, radio transmission systems, relays). Recorded exposure routes for the compound are oral and intravenous.
Contaminant Type
  • Antineoplastic Agent, Phytogenic
  • Drug
  • Ester
  • Ether
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
(-)-EtoposideChEBI
4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside)ChEBI
4-Demethylepipodophyllotoxin beta-D-ethylideneglucosideChEBI
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)-oneChEBI
EposinChEBI
EtopophosChEBI
EtoposidoChEBI
EtoposidumChEBI
LastetChEBI
ToposarChEBI
trans-EtoposideChEBI
VepesidChEBI
VP-16ChEBI
4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-b-D-glucopyranoside)Generator
4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-β-D-glucopyranoside)Generator
4-Demethylepipodophyllotoxin b-D-ethylideneglucosideGenerator
4-Demethylepipodophyllotoxin β-D-ethylideneglucosideGenerator
9-((4,6-O-Ethylidine-b-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)-oneGenerator
9-((4,6-O-Ethylidine-β-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)-oneGenerator
Baxter oncology brand OF etoposideHMDB
Bristol myers brand OF etoposideHMDB
Bristol-myers squibb brand OF etoposideHMDB
Demethyl epipodophyllotoxin ethylidine glucosideHMDB
EtomedacHMDB
Etoposide tevaHMDB
ExitopHMDB
Pierre fabre brand OF etoposideHMDB
Bristol myers squibb brand OF etoposideHMDB
Bristol-myers brand OF etoposideHMDB
CelltopHMDB
Etoposide pierre fabreHMDB
Etoposide, (5a alpha)-isomerHMDB
Etoposide, (5a alpha,9 alpha)-isomerHMDB
Etoposide, alpha-D-glucopyranosyl isomerHMDB
Ferrer brand OF etoposideHMDB
Lemery brand OF etoposideHMDB
Onkoworks brand OF etoposideHMDB
Sanfer brand OF etoposideHMDB
Vépéside sandozHMDB
Ribosepharm brand OF etoposideHMDB
Baxter brand OF etoposideHMDB
EposideHMDB
Eto gryHMDB
Eto-gryHMDB
Etoposide, (5S)-isomerHMDB
Etoposido ferrer farmaHMDB
Gry brand OF etoposideHMDB
Novartis brand OF etoposideHMDB
OnkoposidHMDB
Pharmachemie brand OF etoposideHMDB
RiboposidHMDB
Tedec meiji brand OF etoposideHMDB
EtoposHMDB
Etoposide, alpha D glucopyranosyl isomerHMDB
Medac brand OF etoposideHMDB
Prasfarma brand OF etoposideHMDB
Teva brand OF etoposideHMDB
VP 16HMDB
Vépéside-sandozHMDB
alpha-D-Glucopyranosyl isomer etoposideHMDB
Teva, etoposideHMDB
Chemical FormulaC29H32O13
Average Molecular Mass588.557 g/mol
Monoisotopic Mass588.184 g/mol
CAS Registry Number33419-42-0
IUPAC Name(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one
Traditional Name(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one
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
InChI IdentifierInChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1
InChI KeyVJJPUSNTGOMMGY-MRVIYFEKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydroisoquinolines
Sub ClassNot Available
Direct ParentTetrahydroisoquinolines
Alternative Parents
Substituents
  • Tetrahydroisoquinoline
  • 3-piperidinecarboxamide
  • Piperidinecarboxamide
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • Piperidine
  • Tertiary carboxylic acid amide
  • Tertiary aliphatic amine
  • Amino acid or derivatives
  • Tertiary amine
  • Carboxamide group
  • Carboxylic acid ester
  • Azacycle
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic Effects
  • white colour ?
  • colorless colour ?
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point236 - 251°C
Boiling PointNot Available
Solubility9.78e-01 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.98 g/LALOGPS
logP0.73ALOGPS
logP1.16ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area160.83 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity139.02 m³·mol⁻¹ChemAxon
Polarizability57.95 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0bvi-1901070000-74ac7d5d623bed96366eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0mm1-2900107000-099107e3dc57314671efNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0690000000-25202a61d19d3dfaed8bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0090420000-e5d6bcd633116e0553a0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0190000000-ac64a57347a9295be5dcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0590000000-e0e45774111103754c46Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-0980000000-ccf595459b4b1988d77aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-0950000000-4d3313053107615d463aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0590000000-e653736b252cc5e2e795Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-0980000000-48f8ee63240c179183f6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0090420000-4257cbcff5646216f202Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0590000000-8c7420414be0c3746affNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-0091540000-94d46ba9cac17da0c456Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0930000000-d9d8244725f2e57fce96Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0019-0397150000-e467d625bbc856208c08Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0930000000-2f7ed12e16b6771697e6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0290010000-9da8eeb575b398d3bdbdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0930000000-d15ca68c1981073da181Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-0950000000-4d3313053107615d463aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0390000000-b642957170b052134776Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-0091670000-9a34ca7c7757308b4693Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0390010000-66e8c167b7f76c77b80bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0590000000-e0e45774111103754c46Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-0980000000-ccf595459b4b1988d77aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0190000000-ac64a57347a9295be5dcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0090420000-e5d6bcd633116e0553a0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0490000000-98fe917ae569f2dad3dcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0290010000-ef884518c08ce24544b2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0791000000-1a458ee9b4d2f02a3ee1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0191100000-7608a740f3371996b35aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0590000000-2ec3834e1b815095e60aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0690000000-49232cc1f203f4afd261Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0930000000-aba212495febedd32a12Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0390010000-a84112d8511f443f58c2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0930000000-282e441337e65a47dc64Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0590000000-1b45ac088cf115d38c1cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0290000000-c3041196a27b3df90779Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-0091540000-b4e0de0242ca182b03d4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uei-0106690000-bd98e3ad1ce23f0413c0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-0119510000-51cff21db98c0ed7effdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-0219300000-8bb469d4a7eadf8f5308Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000j-1306090000-5791526d6f416ac328bfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000t-2009030000-3ed5cbe07a1ce3f87bf6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000t-2009000000-41d7c2765f3c44df7f34Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f80-0057890000-b40046bb923663e61038Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001r-0029030000-d51905baa0ef03c8de2dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0569-0229000000-1399af131a3242af89a1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0000090000-9baf08bb7ab51d7e512bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052u-1001090000-3d6e3b8a172c83292737Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-017i-0009040000-d9fa90d104f0c67a2f17Not AvailableView Spectrum
Toxicity Profile
Toxicity Values
Toxicity ValueOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalToxicity RatingReference
897.0 Log mg/kg [500:1600]RatLD50oralpredictedNot AvailableNot Available
Toxicity / Toxin ClassNot Available
Mechanism of ToxicityEtoposide 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.
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (3)
Minimum Risk LevelNot Available
SymptomsSide effects include alopecia, constipation, diarrhea, nausea and vomiting and secondary malignancies (leukemia).
TreatmentNot Available
Health Effects
Health EffectRelationshipDirectionDescriptionReference
lung cancerNot AvailableNot AvailableA respiratory system cancer that is located in the lung. (DO)PMC7763534
lung cancerHas Therapeutic Effect OnNot AvailableA respiratory system cancer that is located in the lung. (DO)PMC11206683
cancerNot AvailableNot AvailableCancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. Possible signs and symptoms include a lump, abnormal bleeding, prolonged cough, unexplained weight loss, and a change in bowel movements. There are over 100 types of cancers affect humans. The risk of developing certain cancers can be reduced by not smoking, maintaining a healthy weight, not drinking too much alcohol, eating plenty of vegetables, fruits and whole grains, vaccination against certain infectious diseases, not eating too much processed and red meat and avoiding too much sunlight exposure. Cancer is often treated with some combination of radiation therapy, surgery, chemotherapy and targeted therapy. The majority of cancers, some 90–95% of cases, are due to genetic mutations from environmental and lifestyle factors. The remaining 5–10% are due to inherited genetics.PMC12993860 , PMC5564849
Alzheimer's diseaseAssociated With?Not AvailableA neurodegenerative disease which causes neural atrophy, leading to dementia and memory loss.PMC6412732
breast cancerNot AvailableNot AvailableA breast cancer that has material basis in abnormally proliferating cells derives from epithelial cells. (DO)PMC11084730
breast cancerHas Therapeutic Effect OnNot AvailableA breast cancer that has material basis in abnormally proliferating cells derives from epithelial cells. (DO)PMC11206683
multiple myelomaNot AvailableNot AvailableA myeloid neoplasm that is located in the plasma cells in bone marrow. (DO)PMC7463238
asthmaNot AvailableNot AvailableA bronchial disease that is characterized by chronic inflammation and narrowing of the airways, which is caused by a combination of environmental and genetic factors. The disease has symptom recurring periods of wheezing (a whistling sound while breathing), has symptom chest tightness, has symptom shortness of breath, has symptom mucus production and has symptom coughing. The symptoms appear due to a variety of triggers such as allergens, irritants, respiratory infections, weather changes, exercise, stress, reflux disease, medications, foods and emotional anxiety. (DO)PMC7835872
feverNot AvailableNot AvailableA disorder characterized by an abnormally high body temperature.PMC4718299
painNot AvailableNot AvailableA disorder characterized by the sensation of marked discomfort, distress or agony. (NCI CTCAE)PMC4718299
Prostate cancerNot AvailableNot AvailableA male reproductive organ cancer that is located in the prostate. (DO)PMC13031462
leukemiaNot AvailableNot AvailableA cancer that affects the blood or bone marrow characterized by an abnormal proliferation of blood cells. (DO)PMC4558124 , PMC7967234
schizophreniaAssociated With?Not AvailableA psychotic disorder that is characterized by a disintegration of thought processes and of emotional responsiveness. (DO)PMC6412732
psoriasisHas Therapeutic Effect OnNot AvailableA disorder characterized by a quicker life span of skin cells causing cells to build up rapidly on the surface of the skin.PMC12752079
glioblastomaNot AvailableNot AvailableA type of brain tumor characterized by its aggressiveness and believed to originate from astrocytes.PMC7022905
lymphomaNot AvailableNot AvailableA hematologic cancer that affects lymphocytes that reside in the lymphatic system and in blood-forming organs. (DO)PMC9323819 , PMC7967234
testicular cancerNot AvailableNot AvailableA male reproductive system cancer that is located in the testicles. (DO)PMC7123643
neuroblastomaNot AvailableNot AvailableAn autonomic nervous system neoplasm that derives from immature nerve cells. (DO)PMC9657890 , PMC12828674
neuroblastomaHas Therapeutic Effect OnNot AvailableAn autonomic nervous system neoplasm that derives from immature nerve cells. (DO)PMC12828674
Parkinson's diseaseAssociated With?Not AvailableA long-term degenerative disorder of the central nervous system that mainly affects the motor system. The symptoms generally come on slowly over time.PMC6412732 , PMC7835872
Kaposi's sarcomaNot AvailableNot AvailableNot AvailablePMC6334177
seminomaNot AvailableNot AvailableA germinoma that has material basis in cells that make sperm and eggs. (DO)PMC10953835
small cell carcinomaNot AvailableNot AvailableNot AvailablePMC4155059
osteosarcomaNot AvailableNot AvailableNot AvailablePMC9657890
rhabdomyosarcomaNot AvailableNot AvailableNot AvailablePMC9657890
cardiac arrestNot AvailableNot AvailableA congestive heart failure characterized by a sudden stop in effective blood circulation due to the failure of the heart to contract effectively or at all.PMC7835872
plasma cell leukemiaNot AvailableNot AvailableNot AvailablePMC6223128 , PMC9387011
mantle cell lymphomaNot AvailableNot AvailableMantle cell lymphoma is a B-cell non-Hodgkin lymphoma (NHL). Lymphoma is a cancer of the lymphatic system, which is part of the body's germ-fighting network. The lymphatic system includes the lymph nodes (lymph glands), spleen, thymus gland, stomach and bone marrow. Mantle cell lymphoma typically develops in the outer edge of a lymph node called the mantle zone. Mantle cell lymphoma occurs more often in men than in women. It is usually diagnosed in people in their early 60s.PMC3004744
myelodysplastic syndromeAssociated With?Not AvailableA bone marrow cancer characterized as the failure of bone marrow to make enough healthy blood cells and thus there are blast cells in the blood and/or bone marrow.PMC7123643
mucositisNot AvailableNot AvailableNot AvailablePMC3935911
embryonal carcinomaNot AvailableNot AvailableNot AvailablePMC4718299
diffuse large B-cell lymphomaNot AvailableNot AvailableNot AvailablePMC7581128
plasmablastic lymphomaNot AvailableNot AvailableNot AvailablePMC9323819
Cell DeathAssociated With?Not AvailableNot AvailablePMC3572937
Cell DeathAssociated With?increaseNot AvailablePMC2679389 , PMC8309170
DNA DamageAssociated With?Not AvailableNot AvailablePMC8480152 , PMC10294509
DNA DamageAssociated With?increaseNot AvailablePMC10294509
DNA DamageAssociated With?decreaseNot AvailablePMC2853120
SepsisNot AvailableNot AvailableNot AvailablePMC7835872
depressive disorderAssociated With?Not AvailableNot AvailablePMC6412732
NeoplasmsNot AvailableNot AvailableNot AvailablePMC7571232
lung non-small cell carcinomaHas Therapeutic Effect OnNot AvailableNot AvailablePMC12290890
anaphylaxisNot AvailableNot AvailableNot AvailablePMC7835872
Neoplasm MetastasisNot AvailableNot AvailableNot AvailablePMC12452751
neoplasmNot AvailableNot AvailableNot AvailablePMC5713456
small cell lung carcinomaNot AvailableNot AvailableNot AvailablePMC6334177 , PMC5164907
Leukemia, Myeloid, AcuteAssociated With?Not AvailableNot AvailablePMC7139235
bone neoplasmNot AvailableNot AvailableNot AvailablePMC13073827
Ewing sarcomaNot AvailableNot AvailableNot AvailablePMC9657890
TeratomaNot AvailableNot AvailableNot AvailablePMC12821418
adrenocortical carcinomaNot AvailableNot AvailableNot AvailablePMC6784971
large cell carcinomaNot AvailableNot AvailableNot AvailablePMC5164907
Sarcoma, EwingNot AvailableNot AvailableNot AvailablePMC4688361
secondary neoplasmAssociated With?increaseNot AvailablePMC7123643
Exposure Sources
Source IDSourceSectorReference
CEDs000010Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.Agriculture & land managementPubChem
CEDs000222Lotions?Lotions are emulsified formulations primarily composed of water, oils, and various active ingredients designed for skin hydration and protection.Personal care & cosmeticsPMC11721023
CEDs000358Antineoplastic agents?Antineoplastic agents are a class of synthetic chemicals used primarily in the treatment of cancer.Healthcare, pharmaceuticals & veterinary productsNot Available
CEDs000506Antennas?Antennas, commonly used in communication technologies, can be a source of synthetic chemical contamination through the materials and coatings used in their construction.Electrical & Electronic EquipmentPubChem
CEDs000517Electric Switches?Electric switches, integral components in numerous devices, can be a source of synthetic chemical contamination due to the materials and manufacturing processes involved in their production.Electrical & Electronic EquipmentPubChem
CEDs000519Electrodes?Electrodes, used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials from which they are constructed and the processes involved in their manufacturing.Electrical & Electronic EquipmentPubChem
CEDs000520Emergency Protective Devices?Emergency protective devices, such as circuit breakers and surge protectors, are essential components in electrical systems designed to prevent damage from overcurrent and surges.Electrical & Electronic EquipmentPubChem
CEDs000530Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.Electrical & Electronic EquipmentPubChem
CEDs000531Relays?Relays are electromechanical switches used to control circuits and manage electrical loads.Electrical & Electronic EquipmentPubChem
CEDs000545Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.Food, food processing & cookwarePubChem
CEDs000552Processing Meats?Processing meats can lead to synthetic chemical contamination primarily through the use of additives and preservatives.Food, food processing & cookwarePubChem
CEDs000564Soap Dispensers?Soap dispensers, commonly used for dispensing liquid soaps and sanitizers, can become a source of synthetic chemical contamination due to the materials used in their construction and the products they dispense.Household cleaning & consumer productsPubChem
CEDs000579Manufacture Of Iron Or Steel?The manufacture of iron or steel involves various processes, including smelting, refining, and alloying, which can result in the release of synthetic chemicals and contaminants.Industrial manufacturing & chemical processingPubChem
CEDs000596Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.Agriculture & land managementPubChem
CEDs000606Plant Growth Regulators?Plant Growth Regulators (PGRs) are synthetic chemicals designed to influence the growth and development of plants.Agriculture & land managementPubChem
CEDs000613Depilatories?Depilatories are products designed to remove unwanted hair through the application of synthetic chemicals that break down the protein structure of hair, facilitating its removal.Personal care & cosmeticsPubChem
CEDs000615Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.Personal care & cosmeticsPubChem
CEDs000632Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.Textiles, leather & furnishingsPubChem
CEDs000642Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.Textiles, leather & furnishingsPubChem
CEDs000667Gaseous Fire Fighting?Gaseous fire fighting systems utilize synthetic chemicals, such as halocarbons and inert gases, to suppress fires through chemical and physical processes.Fire suppression systems & agentsPubChem
CEDs000671Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.Aviation & AerospacePubChem
CEDs000685Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.Building & ConstructionPubChem
CEDs000692Silica Free Oxide Glass?Silica Free Oxide Glass is a type of glass that is produced using alternative materials to traditional silica-based formulations.Building & ConstructionPubChem
CEDs000696Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.Industrial manufacturing & chemical processingPubChem
CEDs000698Jewellery?Jewellery production often involves the use of various synthetic chemicals during the extraction and processing of metals.Mining & metal processingPubChem
CEDs000727Printing Machines Or Presses?Printing machines or presses commonly utilize synthetic chemicals such as inks, solvents, and cleaning agents.Paper, pulp & fiber productsPubChem
CEDs000743Sludge Treatment?Sludge treatment involves the processing of waste materials generated from wastewater treatment plants, which often contain a variety of organic and inorganic substances.Wastewater, sanitation & biosolidsPubChem
CEDs000744Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.Wastewater, sanitation & biosolidsPubChem
CEDs01153Breast MilkFood, food processing & cookwarePMC8122652 , PMC8122652
CEDs01177BreadFood, food processing & cookwarePMC11963836
CEDs01879ResinIndustrial manufacturing & chemical processingPMC11826486 , PMC11174699
CEDs02255WaterAquatic systems & sedimentsPMC10579118 , PMC10579118
CEDs02845CosmeticsPersonal care & cosmeticsPMC11721023
CEDs02847Personal Care ProductsPersonal care & cosmeticsPMC12583126
CEDs03009Waste WaterWastewater, sanitation & biosolidsPMC10579118 , PMC8718386
Pathways
5 pathwaysPathway Source: PathBank
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Caspase-3 structureClick to view 3D structureCaspase-3P42574HumansKnownNot Available
ATP-binding cassette sub-family C member 2 structureClick to view 3D structureATP-binding cassette sub-family C member 2Q92887HumansKnownNot Available
Click to view 3D structureRegulatory protein E2P03118Human papillomavirus type 1aPredicted (SEA)
Prediction Confidence Score
0.514
Applicability Domain
0.514
Statistical Significance
2.00e-05
Supporting Reference Compounds
1
E-value
0.155698
DNA topoisomerase 2-alpha structureClick to view 3D structureDNA topoisomerase 2-alphaP11388HumansPredicted (SEA)
Prediction Confidence Score
0.36
Applicability Domain
1.0
Statistical Significance
1.10e-04
Supporting Reference Compounds
27
E-value
0.856341
Solute carrier organic anion transporter family member 1B3 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B3Q9NPD5HumansPredicted (SEA)
Prediction Confidence Score
0.35
Applicability Domain
1.0
Statistical Significance
6.30e-04
Supporting Reference Compounds
51
E-value
4.9045
Polyunsaturated fatty acid lipoxygenase ALOX15 structureClick to view 3D structurePolyunsaturated fatty acid lipoxygenase ALOX15P12530Oryctolagus cuniculusPredicted (SEA)
Prediction Confidence Score
0.316
Applicability Domain
1.0
Statistical Significance
8.50e-04
Supporting Reference Compounds
47
E-value
6.61718
Nuclear receptor coactivator 3 structureClick to view 3D structureNuclear receptor coactivator 3Q9Y6Q9HumansPredicted (SEA)
Prediction Confidence Score
0.312
Applicability Domain
1.0
Statistical Significance
3.40e-04
Supporting Reference Compounds
41
E-value
2.64687
Caspase-3 structureClick to view 3D structureCaspase-3P42574HumansPredicted (SEA)
Prediction Confidence Score
0.307
Applicability Domain
1.0
Statistical Significance
0.01
Supporting Reference Compounds
125
E-value
77.5378
DNA topoisomerase 2-beta structureClick to view 3D structureDNA topoisomerase 2-betaQ02880HumansPredicted (SEA)
Prediction Confidence Score
0.301
Applicability Domain
1.0
Statistical Significance
1.00e-05
Supporting Reference Compounds
13
E-value
0.0778492
Nuclear receptor coactivator 1 structureClick to view 3D structureNuclear receptor coactivator 1Q15788HumansPredicted (SEA)
Prediction Confidence Score
0.295
Applicability Domain
1.0
Statistical Significance
1.50e-04
Supporting Reference Compounds
22
E-value
1.16774
Prostaglandin G/H synthase 1 structureClick to view 3D structureProstaglandin G/H synthase 1P05979Ovis ariesPredicted (SEA)
Prediction Confidence Score
0.268
Applicability Domain
0.514
Statistical Significance
0.0205
Supporting Reference Compounds
106
E-value
159.28
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)
Prediction Confidence Score
0.259
Applicability Domain
0.514
Statistical Significance
0.4149
Supporting Reference Compounds
1245
E-value
3229.65
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)
Prediction Confidence Score
0.249
Applicability Domain
0.514
Statistical Significance
0.3725
Supporting Reference Compounds
825
E-value
2899.81
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)
Prediction Confidence Score
0.249
Applicability Domain
0.514
Statistical Significance
0.568
Supporting Reference Compounds
1538
E-value
4422.15
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2Q05769Mus musculusPredicted (SEA)
Prediction Confidence Score
0.246
Applicability Domain
0.514
Statistical Significance
0.0148
Supporting Reference Compounds
43
E-value
115.45
D(1A) dopamine receptor structureClick to view 3D structureD(1A) dopamine receptorP21728HumansPredicted (SEA)
Prediction Confidence Score
0.243
Applicability Domain
0.27 Low confidence
Statistical Significance
0.1819
Supporting Reference Compounds
425
E-value
1416.08
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)
Prediction Confidence Score
0.237
Applicability Domain
0.514
Statistical Significance
0.0321
Supporting Reference Compounds
154
E-value
249.662
Tissue factor structureClick to view 3D structureTissue factorP13726HumansPredicted (SEA)
Prediction Confidence Score
0.234
Applicability Domain
0.27 Low confidence
Statistical Significance
0.0172
Supporting Reference Compounds
29
E-value
133.901
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)
Prediction Confidence Score
0.228
Applicability Domain
0.27 Low confidence
Statistical Significance
0.5281
Supporting Reference Compounds
1103
E-value
4111.61
Nuclear receptor subfamily 0 group B member 1 structureClick to view 3D structureNuclear receptor subfamily 0 group B member 1P51843HumansPredicted (SEA)
Prediction Confidence Score
0.223
Applicability Domain
0.514
Statistical Significance
0.0028
Supporting Reference Compounds
17
E-value
21.8756
Tubulin beta chain structureClick to view 3D structureTubulin beta chainQ6B856Bos taurusPredicted (SEA)
Prediction Confidence Score
0.222
Applicability Domain
0.514
Statistical Significance
0.0095
Supporting Reference Compounds
12
E-value
73.7232
Mitogen-activated protein kinase structureClick to view 3D structureMitogen-activated protein kinaseA3FQ79Cryptosporidium parvum (strain Iowa II)KnownNot Available
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)
Prediction Confidence Score
0.219
Applicability Domain
0.27 Low confidence
Statistical Significance
0.594
Supporting Reference Compounds
953
E-value
4624.48
Tubulin alpha chain structureClick to view 3D structureTubulin alpha chainP02550Sus scrofaPredicted (SEA)
Prediction Confidence Score
0.217
Applicability Domain
0.514
Statistical Significance
0.004
Supporting Reference Compounds
9
E-value
31.5289
Click to view 3D structureEndothelin-1 receptorP26684Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.213
Applicability Domain
0.22 Low confidence
Statistical Significance
0.0406
Supporting Reference Compounds
24
E-value
315.834
D(4) dopamine receptor structureClick to view 3D structureD(4) dopamine receptorP21917HumansPredicted (SEA)
Prediction Confidence Score
0.21
Applicability Domain
0.231 Low confidence
Statistical Significance
0.5691
Supporting Reference Compounds
524
E-value
4430.71
Click to view 3D structureUDP-glucuronosyltransferase 1A1P22309HumansKnownNot Available
Click to view 3D structureEndothelin receptor type BP48302Mus musculusPredicted (SEA)
Prediction Confidence Score
0.209
Applicability Domain
0.22 Low confidence
Statistical Significance
0.0082
Supporting Reference Compounds
2
E-value
63.8364
Endothelin-1 receptor structureClick to view 3D structureEndothelin-1 receptorP25101HumansPredicted (SEA)
Prediction Confidence Score
0.209
Applicability Domain
0.22 Low confidence
Statistical Significance
0.0944
Supporting Reference Compounds
51
E-value
734.741
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansKnownNot Available
Albumin structureClick to view 3D structureAlbuminP02768HumansKnownNot Available
DNA topoisomerase 2-alpha structureClick to view 3D structureDNA topoisomerase 2-alphaP11388HumansKnownNot Available
DNA topoisomerase 2-beta structureClick to view 3D structureDNA topoisomerase 2-betaQ02880HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00773
HMDB IDHMDB0014911
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEtoposide
Chemspider ID33510
ChEBI ID4911
PubChem Compound ID36462
Kegg Compound IDC01576
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

DrugSyn.org

MSDSLink
General References
  1. 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: 17578914]
  2. 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: 11531262]
  3. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. - http://monographs.iarc.fr/index.php