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Oncology and immunology drugs

Etoposide

Also known as VePesid, Toposar, trans-Etoposide

CAS 33419-42-0Formula C29H32O13Molar mass 588.56 g/molEC 251-509-1
GHS signal word: Danger. Pictograms: Harmful or irritant, Serious health hazard 110 suppliers listed Drug substance
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Etoposide chemical structure, C29H32O13, CAS 33419-42-0
2D chemical structure

Key facts

What buyers check first

All properties
Appearance
Crystals from methanol
Melting point
236 to 251
Solubility
Very soluble in methanol, chloroform, slightly soluble in ethanol, sparingly soluble in…
HS code
293890
Category
Oncology and immunology drugs
Illustrative photo, a shrink wrapped pallet of kraft paper sacks in a chemical plant
Typical packagingIllustrative packaging image, not the actual product

What is Etoposide?

Plain description, key identifiers and synonyms

Etoposide is a beta-D-glucoside, an organic heterotetracyclic compound and a furonaphthodioxole. It has a role as an antineoplastic agent and a DNA synthesis inhibitor. It is functionally related to a podophyllotoxin and a 4'-demethylepipodophyllotoxin.

Identifiers

Registry numbers, names and line notations, tap to copy

IUPAC name
(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
CAS number
33419-42-0 CAS number cross-checkedOther or deprecated CAS: 121471-01-0
EC number
251-509-1
Molecular formula
C29H32O13
UNII
6PLQ3CP4P3
MDL number
MFCD00869325
InChIKey
VJJPUSNTGOMMGY-MRVIYFEKSA-N
InChI
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
Canonical SMILES
COc1cc(C2c3cc4c(cc3C(OC3OC5COC(C)OC5C(O)C3O)C3COC(=O)C23)OCO4)cc(OC)c1O
Isomeric SMILES
C[C@@H]1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)O[C@H]3[C@H]4COC(=O)[C@@H]4[C@@H](C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O

Synonyms

  • VePesid
  • Toposar
  • trans-Etoposide
  • (-)-Etoposide
  • Lastet
  • Etoposido
  • Etoposidum
  • Eposin
  • Sintopozid
  • VP 16-213
  • 4-Demethylepipodophyllotoxin beta-D-ethylideneglucoside
  • VP 16
  • EPEG
  • VP 16213
  • 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside)
  • 4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-beta-D-glucopyranoside)
  • Eposide
  • 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
  • Etoposide Teva
  • Teva, Etoposide
  • alpha-D-Glucopyranosyl Isomer Etoposide
  • Eto GRY
  • Demethyl Epipodophyllotoxin Ethylidine Glucoside
  • Etoposide, alpha D Glucopyranosyl
  • VP 16 213
Show all 34 synonyms
  • 9-((4,6-O-Ethylidene-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one
  • Zuyeyidal
  • Etoposide (VP16)
  • Vepesid J
  • VP 16 (pharmaceutical)
  • Epipodophyllotoxin VP-16213
  • NK 171
  • Etosid
  • Etopophos (phosphate salt)

Physical and chemical properties

Measured values and descriptors computed from the structure

Physical and chemical properties

Measured values, check the supplier specification for your grade

Appearance
Crystals from methanolexp.
Melting point
236 to 251exp.
Solubility
Very soluble in methanol, chloroform, slightly soluble in ethanol, sparingly soluble in water.exp.
Vapour pressure
5.4 × 10⁻²³ mm Hg at 25 °C /Estimated/exp.

Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.

Computed descriptors

Calculated from the structure, useful for screening and formulation

Molecular weight
588.56 g/molcalc.
Exact mass
588.1843 Dacalc.
LogP (octanol/water)
1.34calc.
Topological polar surface area
160.8 Ųcalc.
Hydrogen bond donors
3calc.
Hydrogen bond acceptors
13calc.
Rotatable bonds
5calc.
Heavy atoms
42calc.
Rings
7calc.
Aromatic rings
2calc.
Fraction sp3 carbons
0.55calc.
Formal charge
0calc.
Stereocentres
10calc.
Lipinski rule of five
Fails (2 violations)calc.

Calculated for screening. Confirm critical figures with the supplier.

Murcko scaffold

The ring system that remains when every side chain is removed

Murcko scaffold of this chemical, O=C1OCC2C(OC3CCC4OCOCC4O3)c3cc4c(cc3C(c3ccccc3)C12)OCO4

O=C1OCC2C(OC3CCC4OCOCC4O3)c3cc4c(cc3C(c3ccccc3)C12)OCO4

7 rings, 34 atoms.

15 other chemicals share this scaffold

Safety and hazards

GHS classification summary, not a safety data sheet

GHS signal word
Danger
GHS07: Harmful or irritant
Harmful or irritant
GHS08: Serious health hazard
Serious health hazard

Hazard statements

  • H302Harmful if swallowed.
  • H350May cause cancer.
Precautionary statements (9)
  • P203Obtain, read and follow all safety instructions before use.
  • P264Wash skin thoroughly after handling.
  • P270Do not eat, drink or smoke when using this product.
  • P280Wear protective gloves, protective clothing, eye protection and face protection.
  • P301 + P317If swallowed: Get medical help.
  • P318If exposed or concerned, get medical advice.
  • P330Rinse mouth.
  • P405Store locked up.
  • P501Dispose of contents and container in accordance with local regulations.

GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.

Full safety data and first aid

Etoposide suppliers

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Where suppliers are based

110 suppliers in 19 countries

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Etoposide price

Indicative price range per kg from live supplier offers

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Uses and applications

What the substance is used for, by industry and function

Antineoplastic.

Industries and functions

Pharmacological actions

  • Antineoplastic Agents, Phytogenic
  • Topoisomerase II Inhibitors

Roles

  • DNA synthesis inhibitor
  • antineoplastic agent
  • enzyme inhibitor
  • pathway inhibitor
  • pharmaceutical

Pharmacology

Etoposide is a Topoisomerase Inhibitor. The mechanism of action of etoposide is as a Topoisomerase Inhibitor.

How it is made

Semisynthetic glycoside derivative of podophyllotoxin.

Etoposide can be synthesized from naturally occurring podophyllotoxin by first treating the podophyllotoxin with hydrogen bromide to produce 1-bromo-1-deoxyepipodophyllotoxin, which is demethylated to 1-bromo-4'-demethylepipodophyllotoxin. The bromine is replaced by a hydroxy group, resulting in 4'-demethylepipodophyllotoxin. After protection of the phenolic hydroxyl, the 4-hydroxy group is coupled with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranose. The protecting group at the 4'- hydroxy is removed by hydrogenolysis and the acyl groups by hydrolysis, and the cyclic O-4,6 acetal is formed by reaction with acetaldehyde dimethyl acetal.

Regulatory status

Inventories, regulations and trade controls that list this substance

Health and food

  • Active ingredient in FDA approved drug labels

HS code and trade data

Customs classification and reported world trade statistics

Global trade

World import and export statistics for the HS code Etoposide is traded under.

HS 2938.90Indicative HS code

Natural or reproduced by synthesis, other than rutoside (rutin) and its derivatives

World exports in 2024
$1.4B
−8.3% vs 2023, imports $1.35B
2019 to 2024
Top exporters
  1. China49.2%
  2. France * partner reported8.9%
  3. Malaysia6.1%
Top importers
  1. United States22.3%
  2. India * partner reported7.8%
  3. Brazil5.5%

* Partner reported figures, a lower bound.

Reported customs values in USD, not prices.Full trade data

The HS code shown for Etoposide is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.

Frequently asked questions

Quick answers about Etoposide, based on the data on this page

What is Etoposide?

Etoposide is a beta-D-glucoside, an organic heterotetracyclic compound and a furonaphthodioxole. It has a role as an antineoplastic agent and a DNA synthesis inhibitor. It is functionally related to a podophyllotoxin and a 4'-demethylepipodophyllotoxin.

Is Etoposide hazardous?

Etoposide carries the GHS signal word "Danger". Main hazards: harmful if swallowed, may cause cancer. This summary is not an SDS, always read the supplier safety data sheet.

Guides for buyers

Practical guides that help when you source, ship or handle Etoposide

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Data last updated 7 Oct 2026. Details may have changed, please confirm them with the supplier. Report an error on this page
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