Etoposide

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Etoposide are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Etoposide?

The molecule Etoposide presents a molecular formula of C29H32O13 and its IUPAC name is (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.

Etoposide (Etopophos) is a chemotherapy medication used to treat a number of types of cancer. This includes testicular cancer, ovarian cancer, breast cancer, lung cancer, and leukemia. Etoposide is also used in the treatment of brain tumors..

Etoposide works by inhibiting the growth of cancer cells. It does this by interfering with the ability of the cells to divide. Etoposide also kills cancer cells by inducing apoptosis (cell death)..

Etoposide is typically given as an intravenous (IV) infusion over a period of 1 to 5 hours. The infusion can be given daily, weekly, or every other week. The dosage and schedule depends on the type and stage of cancer being treated..

Common side effects of etoposide include nausea, vomiting, diarrhea, hair loss, and fatigue. Etoposide can also cause low blood counts, which can lead to an increased risk of infection and bleeding..

Etoposide is a potentially toxic medication and should be used with caution. It is important to consult with a healthcare professional prior to starting treatment to ensure that etoposide is the best option for you..

3D structure

Cartesian coordinates

Geometry of Etoposide in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Etoposide VJJPUSNTGOMMGY-MRVIYFEKSA-N chemical compound 2D structure molecule svg
Etoposide

 

Molecule descriptors

 
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
InChI codeInChI=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
SMILESCOc1cc([C@@H]2c3cc4c(cc3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (-)-Etoposide
  • (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(9),2,7-trien-12-one
  • (10r,11r,15r,16s)-16-([(2r,4ar,7r,8r,8as)-7,8-dihydroxy-2-methyl-hexahydro-2h-pyrano[3,2-d][1,3]diox
  • (5R,5AR,8AR,9S)-9-((4,6-O-((1R)-ETHANE-1,1-DIYL)-.ALPHA.-D-GLUCOPYRANOSYL)OXY)-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-5,8,8A,9-TETRAHYDRO(2)BENZOFURO(5,6-F)(1,3)BENZODIOXOL-6(5AH)-ONE
  • (5R,5AR,8aR,9S)-9-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahy
  • (5R,5aR,8aR,9S)-9-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one
  • (5R,5aR,8aR,9S)-9-(((4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one
  • (5R,5aR,8aR,9S)-9-[[4,6-O-(1R)-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
  • (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-dimethoxy-phenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[5,6-f][1,3]benzodioxol-8-one
  • (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[5,6-f]
  • (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
  • (5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3'',4'':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-[(1R)-ethylidene]-beta-D-glucopyranoside
  • (5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol -5-yl 4,6-O-[(1R)-ethylidene]-beta-D-glucopyranoside
  • (5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-[(1R)-ethylidene]-beta-D-glucopyranoside
  • 121471-01-0
  • 33419-42-0
  • 4''-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside)
  • 4'-DEMETHYLEPIPODOPHYLLOTOXIN 9-(4,6-O-(R)-ETHYLIDENE-.BETA.-D-GLUCOPYRANOSIDE)
  • 4'-Demethyl-epipodophyllotoxin 9-[4,6-O-(R)-ethylidene-beta-D-glucopyranoside
  • 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside)
  • 4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-beta-D-glucopyranoside)
  • 4'-Demethylepipodophyllotoxin ethylidene-.beta.-D-glucoside
  • 4'-O-Demethyl-1-O-(4,6-O-ethylidene-beta-D-glucopyranosyl)epipodophyllotoxin
  • 4-Demethylepipodophyllotoxin beta-D-ethylideneglucoside
  • 419E420
  • 6PLQ3CP4P3
  • 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, (5R-(5alpha,5abeta,8aalpha,9beta(R*)))-
  • 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
  • 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
  • 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
  • AB00438905
  • AB00438905-17
  • AB00438905-18
  • AB00438905_19
  • AS-35312
  • BCP9000669
  • BDBM50127140
  • BE164434
  • BPBio1_000673
  • BSPBio_000611
  • C01576
  • CCG-101165
  • CCRIS 2392
  • CPD000112002
  • CS-1774
  • D00125
  • DB00773
  • Demethylepipodophyllotoxin-beta-D-ethylideneglucoside
  • EVP
  • EX-A1207
  • Epipodophyllotoxin VP-16213
  • Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-beta-D-glucopyranoside
  • Epipodophyllotoxin, 4'-demethyl-, 9-(4,6-O-ethylidene-beta-D-glucopyranoside)
  • Epipodophyllotoxin-beta-D-ethyliden-glucoside, 4'-demethyl-
  • Etopol
  • Etopophos (phosphate salt)
  • Etoposide
  • Etoposide (JP17/USP/INN)
  • Etoposide (VP-16)
  • Etoposide (VP16)
  • Etoposide - CAS 33419-42-0
  • Etoposide resolution mixture
  • Etoposide,(S)
  • Etoposide; VP-16
  • Etoposido
  • Etoposidum
  • Etosid
  • FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE-, 9-((4,6-O-ETHYLIDENE-.BETA.-D-GLUCOPYRANOSYL)OXY)5,8,8A,9-TETRAHYDRO-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL), (5R-(5.ALPHA.,5A.BETA.,8A.ALPHA.,9.BETA.(R*)))-
  • Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 9-((4,6-O-(1R)-ethylidene-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-
  • Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one-, 9-((4,6-O-ethylidene-beta-D-glucopyranosyl)oxy)5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl), (5R-(5alpha,5abeta,8aalpha,9beta(R*)))-
  • Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[[4,6-O-(1R)-ethylidene-.beta.-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-
  • GTPL6815
  • HMS2052N05
  • HMS2089F14
  • HMS2096O13
  • HMS2232L03
  • HMS3713O13
  • HSDB 6517
  • HY-13629
  • Lastet
  • MFCD00869325
  • MLS000049957
  • MLS001074951
  • MLS001424283
  • MLS002153463
  • MLS002207239
  • MLS002222184
  • NC00415
  • NCGC00179504-02
  • NK 171
  • NSC 141540
  • NSC-141540
  • NSC141540
  • Prestwick3_000396
  • Q418817
  • SBI-0051910.P002
  • SDCCGSBI-0050405.P002
  • SMR000112002
  • SR-01000763196
  • SR-01000763196-3
  • Sintopozid
  • Toposar
  • VP 16
  • VP 16 (pharmaceutical)
  • VP 16-213
  • VP 16213
  • VP-16
  • VP-16-213
  • VePesid
  • Vepesid J
  • Zuyeyidal
  • [1,3]benzodioxol-8-one
  • [5R-[5?,5a?,8a?,9?(R*)]]-9-[(4,6-?-Ethylidene-?-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
  • etoposide
  • etoposide4-o-b-d-galactopyranoside
  • s1225
  • trans-Etoposide

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3938684
  • UNII-6PLQ3CP4P3
  • AKOS007930275
  • BRD-K37798499-001-02-5
  • BRD-K37798499-001-05-8
  • BRD-K37798499-001-10-8
  • BRD-K37798499-001-14-0
  • BRD-K37798499-001-27-2
  • DTXSID5023035
  • CHEMBL44657
  • CHEBI:4911
  • EINECS 251-509-1
  • SCHEMBL4259

Physico-Chemical properties

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
Molecular formulaC29H32O13
Molecular weight588.557
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity139.11
LogP1.3
Topological polar surface area160.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.