ContaminantDB: Etoposide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2014-09-11 02:05:21 UTC

Update Date

2026-03-31 17:50:04 UTC

Accession Number

CHEM003653

Identification

Common Name

Etoposide

Class

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.

Contaminant Sources

HMDB Contaminants - Urine
IARC Carcinogens Group 1
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Antineoplastic Agent, Phytogenic
Drug
Ester
Ether
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Etoposide	ChEBI
4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside)	ChEBI
4-Demethylepipodophyllotoxin beta-D-ethylideneglucoside	ChEBI
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	ChEBI
Eposin	ChEBI
Etopophos	ChEBI
Etoposido	ChEBI
Etoposidum	ChEBI
Lastet	ChEBI
Toposar	ChEBI
trans-Etoposide	ChEBI
Vepesid	ChEBI
VP-16	ChEBI
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-ethylideneglucoside	Generator
4-Demethylepipodophyllotoxin β-D-ethylideneglucoside	Generator
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)-one	Generator
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)-one	Generator
Baxter oncology brand OF etoposide	HMDB
Bristol myers brand OF etoposide	HMDB
Bristol-myers squibb brand OF etoposide	HMDB
Demethyl epipodophyllotoxin ethylidine glucoside	HMDB
Etomedac	HMDB
Etoposide teva	HMDB
Exitop	HMDB
Pierre fabre brand OF etoposide	HMDB
Bristol myers squibb brand OF etoposide	HMDB
Bristol-myers brand OF etoposide	HMDB
Celltop	HMDB
Etoposide pierre fabre	HMDB
Etoposide, (5a alpha)-isomer	HMDB
Etoposide, (5a alpha,9 alpha)-isomer	HMDB
Etoposide, alpha-D-glucopyranosyl isomer	HMDB
Ferrer brand OF etoposide	HMDB
Lemery brand OF etoposide	HMDB
Onkoworks brand OF etoposide	HMDB
Sanfer brand OF etoposide	HMDB
Vépéside sandoz	HMDB
Ribosepharm brand OF etoposide	HMDB
Baxter brand OF etoposide	HMDB
Eposide	HMDB
Eto gry	HMDB
Eto-gry	HMDB
Etoposide, (5S)-isomer	HMDB
Etoposido ferrer farma	HMDB
Gry brand OF etoposide	HMDB
Novartis brand OF etoposide	HMDB
Onkoposid	HMDB
Pharmachemie brand OF etoposide	HMDB
Riboposid	HMDB
Tedec meiji brand OF etoposide	HMDB
Etopos	HMDB
Etoposide, alpha D glucopyranosyl isomer	HMDB
Medac brand OF etoposide	HMDB
Prasfarma brand OF etoposide	HMDB
Teva brand OF etoposide	HMDB
VP 16	HMDB
Vépéside-sandoz	HMDB
alpha-D-Glucopyranosyl isomer etoposide	HMDB
Teva, etoposide	HMDB

Chemical Formula

C₂₉H₃₂O₁₃

Average Molecular Mass

588.557 g/mol

Monoisotopic Mass

588.184 g/mol

CAS Registry Number

33419-42-0

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

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 Identifier

InChI=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 Key

VJJPUSNTGOMMGY-MRVIYFEKSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:27662 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	236 - 251°C
Boiling Point	Not Available
Solubility	9.78e-01 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.98 g/L	ALOGPS
logP	0.73	ALOGPS
logP	1.16	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	160.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	139.02 m³·mol⁻¹	ChemAxon
Polarizability	57.95 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bvi-1901070000-74ac7d5d623bed96366e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0mm1-2900107000-099107e3dc57314671ef	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Etoposide,1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004r-0690000000-25202a61d19d3dfaed8b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004r-0090420000-e5d6bcd633116e0553a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0190000000-ac64a57347a9295be5dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004r-0590000000-e0e45774111103754c46	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-002r-0980000000-ccf595459b4b1988d77a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-002r-0950000000-4d3313053107615d463a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004r-0590000000-e653736b252cc5e2e795	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-002r-0980000000-48f8ee63240c179183f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004r-0090420000-4257cbcff5646216f202	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-004r-0590000000-8c7420414be0c3746aff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-002r-0091540000-94d46ba9cac17da0c456	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0930000000-d9d8244725f2e57fce96	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0019-0397150000-e467d625bbc856208c08	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-0930000000-2f7ed12e16b6771697e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-004i-0290010000-9da8eeb575b398d3bdbd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-0930000000-d15ca68c1981073da181	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-002r-0950000000-4d3313053107615d463a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-004i-0390000000-b642957170b052134776	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-002r-0091670000-9a34ca7c7757308b4693	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uei-0106690000-bd98e3ad1ce23f0413c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-0119510000-51cff21db98c0ed7effd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-0219300000-8bb469d4a7eadf8f5308	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000j-1306090000-5791526d6f416ac328bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000t-2009030000-3ed5cbe07a1ce3f87bf6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000t-2009000000-41d7c2765f3c44df7f34	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

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.

Mechanism of Toxicity

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.

Metabolism

Primarily hepatic (through O-demethylation via the CYP450 3A4 isoenzyme pathway) with 40% excreted unchanged in the urine. Etoposide also undergoes glutathione and glucuronide conjugation which are catalyzed by GSTT1/GSTP1 and UGT1A1, respectively. Prostaglandin synthases are also responsible for the conversion of etoposide to O-demethylated metabolites (quinone). 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. 56% of the dose was in the urine, 45% of which was excreted as etoposide. Half Life: 4-11 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

1, carcinogenic to humans. (3)

Uses/Sources

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.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Side effects include alopecia, constipation, diarrhea, nausea and vomiting and secondary malignancies (leukemia).

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID