Compound: etoposide
SMILES: O=C1OC[C@H]2[C@H]1[C@@H](c3c(cc4OCOc4c3)[C@H]2O[C@@H]5O[C@H]6[C@@H](O[C@H](C)OC6)[C@@H]([C@H]5O)O)c7cc(OC)c(O)c(c7)OC
InChIKey: VJJPUSNTGOMMGY-MRVIYFEKSA-N
Synonyms: etoposide, 33419-42-0, VePesid, Toposar, trans-Etoposide, (-)-Etoposide, Lastet, Etoposido, Etoposidum, Eposin, Sintopozid, VP-16-213, VP 16-213, NSC-141540, 4-Demethylepipodophyllotoxin beta-D-ethylideneglucoside, VP 16, EPEG, VP 16213, 6PLQ3CP4P3, 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside), NSC 141540, DTXSID5023035, CHEBI:4911, DTXCID601473876, Eposide, 4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-beta-D-glucopyranoside), (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, 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, 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*)))-, NSC141540, (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, Etoposide Teva, Teva, Etoposide, alpha-D-Glucopyranosyl Isomer 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, (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, Eto GRY, RefChem:56691, Demethyl Epipodophyllotoxin Ethylidine Glucoside, L01CB01, Etoposide, alpha D Glucopyranosyl, VP 16 213, (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(7.7.0.03,7.011,15)hexadeca-1,3(7),8-trien-12-one, (5R,5aR,8aR,9S)-9-((4,6-O-(1R)-Ethylidene-beta-D-glucopyranosyl)oxy)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro(3',4':6,7)naphtho(2,3-d)(1,3)dioxol-6(5aH)-one, 251-509-1, 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, Etoposidum [INN-Latin], VP-16, Etoposide (VP16), Vepesid J, Etoposide (VP-16), VP 16 (pharmaceutical), Epipodophyllotoxin VP-16213, CHEMBL44657, NK 171, Etosid, C29H32O13, Etoposido [INN-Spanish], (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, Etopophos (phosphate salt), Etopol, (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, SMR000112002, ol-6(8H)-one, CCRIS 2392, HSDB 6517, VePESID (TN), EINECS 251-509-1, UNII-6PLQ3CP4P3, 4'-Demethylepipodophyllotoxin ethylidene-.beta.-D-glucoside, Vespid, Etopophos;, Abiposid;, Vepeside;, Amizide;, Citodox;, Toposar;, Vepesid;, Etoposide CRS, Exitop;, NCGC00016821-01, (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, (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, EPE, EVP, 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)-, Demethylepipodophyllotoxin-beta-D-ethylideneglucoside, 4'-O-Demethyl-1-O-(4,6-O-ethylidene-beta-D-glucopyranosyl)epipodophyllotoxin, Epipodophyllotoxin, 4'-demethyl-, 9-(4,6-O-ethylidene-beta-D-glucopyranoside), CAS-33419-42-0, AVOPEF, Etoposide (Standard), Etoposide [USAN:USP:INN:BAN:JAN], Etoposide; VP-16, CPD000112002, Epipodophyllotoxin-beta-D-ethyliden-glucoside, 4'-demethyl-, ETOPOSIDE [INN], ETOPOSIDE [JAN], ETOPOSIDE [MI], ETOPOSIDE [HSDB], ETOPOSIDE [IARC], ETOPOSIDE [USAN], Prestwick3_000396, ETOPOSIDE [VANDF], ETOPOSIDE [MART.], Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-beta-D-glucopyranoside, ETOPOSIDE [USP-RS], ETOPOSIDE [WHO-DD], ETOPOSIDE [WHO-IP], SCHEMBL4259, BSPBio_000611, 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, MLS000049957, MLS001074951, MLS001424283, MLS002153463, MLS002207239, MLS002222184, Etoposide - Bio-X trade mark, Etoposide (JP18/USP/INN), BPBio1_000673, GTPL6815, orb1310906, orb3141266, ETOPOSIDE [EP IMPURITY], ETOPOSIDE [ORANGE BOOK], ETOPOSIDE [EP MONOGRAPH], ETOPOSIDE [USP IMPURITY], SCHEMBL29653657, ETOPOSIDE [USP MONOGRAPH], ETOPOSIDUM [WHO-IP LATIN], HMS2052N05, HMS2089F14, HMS2096O13, HMS2232L03, HMS3713O13, HMS6018O17, EX-A1207, Tox21_110630, Tox21_302201, BDBM50127140, EBC-11154, Etoposide for system suitability CRS, HY-13629R, MSK001347, s1225, Etoposide - CAS 33419-42-0, AKOS007930275, CCG-101165, CS-1774, DB00773, Etoposide, synthetic, >=98%, powder, ME09941, NC00415, SDCCGSBI-0050405.P002, 4'-Demethyl-epipodophyllotoxin 9-[4,6-O-(R)-ethylidene-beta-D-glucopyranoside, NCGC00179504-02, NCGC00255126-01, AS-35312, BE164434, HY-13629, SBI-0051910.P002, AB00438905, NS00009585, T0132, EN300-97099, C01576, D00125, AB00438905-17, AB00438905-18, AB00438905_19, Q418817, SR-01000763196, SR-01000763196-3, BRD-K37798499-001-02-5, BRD-K37798499-001-05-8, BRD-K37798499-001-10-8, BRD-K37798499-001-14-0, BRD-K37798499-001-18-1, BRD-K37798499-001-21-5, BRD-K37798499-001-22-3, BRD-K37798499-001-25-6, BRD-K37798499-001-27-2, -5-yl 4,6-O-[(1R)-ethylidene]-beta-D-glucopyranoside, Etoposide, British Pharmacopoeia (BP) Reference Standard, Z1304065033, Etoposide, European Pharmacopoeia (EP) Reference Standard, Etoposide, United States Pharmacopeia (USP) Reference Standard, 4?-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-b-D-glucopyranoside), 4''-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside), 4'-DEMETHYLEPIPODOPHYLLOTOXIN 9-(4,6-O-(R)-ETHYLIDENE-.BETA.-D-GLUCOPYRANOSIDE), Etoposide for system suitability, European Pharmacopoeia (EP) Reference Standard, (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]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-[[4,6-O-(1R)-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, (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-dimethoxy-phenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[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-hexahydro-2H-furo[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, 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, 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*)))-
Theoretical properties:
molecular_formula: C29H32O13
molecular_weight: 588.6 g/mol
exact_mass: 588.18429107 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 13
rotatable_bond_count: 5
heavy_atom_count: 42
topological_polar_surface_area: 161 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from methanol
color: Crystals from methanol
melting_point: 236-251 °C
solubility: Sparingly soluble
vapor_pressure: 5.4X10-23 mm Hg at 25 °C /Estimated/
Descriptions:
pubchem: Etoposide can cause cancer according to California Labor Code. It can cause developmental toxicity according to state or federal government labeling requirements.
chembl: ETOPOSIDE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Etoposide, sold under the brand name Vepesid among others, is a chemotherapy medication used for the treatments of a number of types of cancer including testicular cancer, lung cancer, lymphoma, leukemia, neuroblastoma, and ovarian cancer. It is also used for hemophagocytic lymphohistiocytosis. It is used by mouth or injection into a vein.
Side effects are very common. They can include low blood cell counts, vomiting, loss of appetite, diarrhea, hair loss, and fever. Other severe side effects include allergic reactions and low blood pressure. Use during pregnancy will likely harm the fetus. Etoposide is in the topoisomerase inhibitor family of medication. It is believed to work by damaging DNA.
Etoposide was approved for medical use in the United States in 1983. It is on the World Health Organization's List of Essential Medicines.