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Substance Name: Etoposide [USAN:USP:INN:BAN:JAN]
RN: 33419-42-0
UNII: 6PLQ3CP4P3
InChIKey: VJJPUSNTGOMMGY-MRVIYFEKSA-N

Note

  • 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.

Molecular Formula

  • C29-H32-O13

Molecular Weight

  • 588.5588
 

Classification Codes

Classification Codes

  • Antineoplastic
  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic
  • DNA Topoisomerase II Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Reproductive Effect
  • Topoisomerase II Inhibitors
  • Topoisomerase Inhibitors

Superlist Classification Code

  • Overall Carcinogenic Evaluation: 2A

Names and Synonyms

Name of Substance

  • Etoposide
  • Etoposide [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Etoposide

Synonyms

  • (-)-Etoposide
  • 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside)
  • 4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-beta-D-glucopyranoside)
  • 4'-O-Demethyl-1-O-(4,6-O-ethylidene-beta-D-glucopyranosyl)epipodophyllotoxin
  • 4-Demethylepipodophyllotoxin beta-D-ethylideneglucoside
  • 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
  • CCRIS 2392
  • EINECS 251-509-1
  • Epipodophyllotoxin VP-16213
  • Epipodophyllotoxin, 4'-demethyl-, 9-(4,6-O-ethylidene-beta-D-glucopyranoside)
  • Epipodophyllotoxin-beta-D-ethyliden-glucoside, 4'-demethyl-
  • Etopophos (phosphate salt)
  • Etoposide
  • Etoposido
  • Etoposido [INN-Spanish]
  • Etoposidum
  • Etoposidum [INN-Latin]
  • HSDB 6517
  • Lastet
  • NK 171
  • NSC 141540
  • Toposar
  • trans-Etoposide
  • UNII-6PLQ3CP4P3
  • VePesid
  • Vepesid J
  • VP 16
  • VP 16 (pharmaceutical)
  • VP 16-213
  • VP 16213
  • VP-16
  • VP-16-213
  • Zuyeyidal

Systematic Names

  • Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-beta-D-glucopyranoside (8CI)
  • Epipodophyllotoxin-beta-D-ethyliden-glucoside, 4'-demethyl-
  • Etoposide
  • Etoposide (VP16)
  • 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*)))-

Superlist Name

  • Etoposide

Registry Numbers

CAS Registry Number

  • 33419-42-0

FDA UNII

  • 6PLQ3CP4P3

Other Registry Numbers

  • 121471-01-0
  • 136598-18-0
  • 201594-04-9
  • 35317-32-9
  • 51854-34-3
  • 76576-58-4

System Generated Number

  • 0033419420

Structure Descriptors

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

InChIKey

VJJPUSNTGOMMGY-MRVIYFEKSA-N

Smiles

COc1cc(cc(OC)c1O)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](O[C@@H]4O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]4O)c6cc7OCOc7cc26

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo intravenous 183mg/kg/2H-C (183mg/kg) BEHAVIORAL: ATAXIA Drug Intelligence and Clinical Pharmacy. Vol. 22, Pg. 41, 1988.
human TDLo intravenous 2630ug/kg/10D (2.63mg/kg) BLOOD: AGRANULOCYTOSIS

BLOOD: APLASTIC ANEMIA

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE
Cancer Vol. 34, Pg. 985, 1974.
human TDLo oral 16mg/kg/5D-I (16mg/kg) BLOOD: AGRANULOCYTOSIS

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE

BLOOD: APLASTIC ANEMIA
Cancer Vol. 34, Pg. 985, 1974.
man TDLo intravenous 57ug/kg/2M-C (0.057mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Lancet. Vol. 341, Pg. 1353, 1993.
mouse LD50 intraperitoneal 64mg/kg (64mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 3473, 1985.
mouse LD50 intravenous 15070ug/kg (15.07mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 oral 215mg/kg (215mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 subcutaneous 143mg/kg (143mg/kg)   Drugs in Japan Vol. -, Pg. 190, 1990.
rabbit LD50 intravenous 37mg/kg (37mg/kg)   Journal of Toxicological Sciences. Vol. 11(Suppl,
rabbit LD50 oral 147mg/kg (147mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Journal of Toxicological Sciences. Vol. 11(Suppl,
rat LD50 intraperitoneal 39mg/kg (39mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 3473, 1985.
rat LD50 intravenous 58mg/kg (58mg/kg)   Drugs in Japan Vol. -, Pg. 230, 1995.
rat LD50 oral 1784mg/kg (1784mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 3473, 1985.
rat LD50 oral 1784mg/kg (1784mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 3473, 1985.
rat LD50 subcutaneous > 200mg/kg (200mg/kg)   Drugs in Japan Vol. -, Pg. 190, 1990.
women TDLo intravenous 160ug/kg/3M-C (0.16mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Lancet. Vol. 341, Pg. 1353, 1993.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 236-251 deg C   EXP
log P (octanol-water) 0.6 (none)   EXP
Water Solubility 58.7 mg/L 25 EST
Vapor Pressure 5.35E-23 mm Hg 25 EST
Henry's Law Constant 1.75E-30 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.05E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.