Etoposide

Suppliers

Names

[ CAS No. ]:
33419-42-0

[ Name ]:
Etoposide

[Synonym ]:
(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)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
VP-16-213
4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-β-D-glucopyranoside)
Vepeside
Etoposide
4'-Demethylepipodophyllotoxin ethylidene-β-D-glucoside
EPEG
MFCD00869325
Etoposide [USAN:BAN:INN:JAN]
Etoposide USP26
Etoposide (VP16)
(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]-β-D-glucopyranoside
(5R,5aR,8aR,9S)-9-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-méthylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy}-5-(4-hydroxy-3,5-diméthoxyphényl)-5,8,8a,9-tétrahydrofuro[3',4':6,7]naphto[2,3-d][1,3]dioxol-6(5aH)-one
4′-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-β-D-glucopyranoside)
Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[[4,6-O-[(1R)-ethylidene]-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-
4‘-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-β-D-glucopyranoside)
EINECS 251-509-1

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
798.1±60.0 °C at 760 mmHg

[ Melting Point ]:
236-251ºC

[ Molecular Formula ]:
C29H32O13

[ Molecular Weight ]:
588.557

[ Flash Point ]:
263.6±26.4 °C

[ Exact Mass ]:
588.184265

[ PSA ]:
160.83000

[ LogP ]:
0.30

[ Vapour Pressure ]:
0.0±3.0 mmHg at 25°C

[ Index of Refraction ]:
1.662

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KC0190000
CHEMICAL NAME :
Epipodophyllotoxin-beta-D-ethyliden-glucoside, 4'-demethyl-
CAS REGISTRY NUMBER :
33419-42-0
LAST UPDATED :
199806
DATA ITEMS CITED :
90
MOLECULAR FORMULA :
C29-H32-O13
MOLECULAR WEIGHT :
588.61

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
16 mg/kg/5D-I
TOXIC EFFECTS :
Blood - agranulocytosis Blood - aplastic anemia Blood - changes in bone marrow (not otherwise specified)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
160 ug/kg/3M-C
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human
DOSE/DURATION :
2630 ug/kg/10D-I
TOXIC EFFECTS :
Blood - agranulocytosis Blood - aplastic anemia Blood - changes in bone marrow (not otherwise specified)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
183 mg/kg/2H-C
TOXIC EFFECTS :
Behavioral - ataxia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
57 ug/kg/2M-C
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1784 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - body temperature decrease
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
39 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
58 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
215 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
64 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - ulceration or bleeding from stomach Skin and Appendages - hair
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
143 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
15070 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
147 mg/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Skin and Appendages - hair Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
37 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1400 mg/kg/5W-C
TOXIC EFFECTS :
Endocrine - other changes Blood - normocytic anemia Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1820 mg/kg/26W-C
TOXIC EFFECTS :
Endocrine - other changes Blood - changes in spleen
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
56 mg/kg/5W-C
TOXIC EFFECTS :
Liver - other changes Endocrine - other changes Blood - normocytic anemia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
182 mg/kg/26W-C
TOXIC EFFECTS :
Endocrine - other changes Blood - normocytic anemia Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
700 mg/kg/5W-C
TOXIC EFFECTS :
Endocrine - other changes Blood - normocytic anemia Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
1165 mg/kg/26W-C
TOXIC EFFECTS :
Endocrine - other changes Blood - normocytic anemia Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
70 mg/kg/5W-C
TOXIC EFFECTS :
Endocrine - other changes Blood - normocytic anemia Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
116 mg/kg/26W-C
TOXIC EFFECTS :
Endocrine - other changes Blood - normocytic anemia Skin and Appendages - dermatitis, other (after systemic exposure)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
312 mg/kg
SEX/DURATION :
female 17-21 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
14630 ug/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
132 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
44 mg/kg
SEX/DURATION :
multigenerations
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
14 mg/kg
SEX/DURATION :
male 5 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
45 mg/kg
SEX/DURATION :
male 90 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
1400 mg/kg
SEX/DURATION :
male 28 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
2 mg/kg
SEX/DURATION :
female 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1500 ug/kg
SEX/DURATION :
female 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - oogenesis Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
70 mg/kg
SEX/DURATION :
male 5 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
29120 ug/kg
SEX/DURATION :
male 26 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Unscheduled DNA synthesis
TYPE OF TEST :
DNA inhibition
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
DNA damage
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Sister chromatid exchange

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Mammal - species unspecified Ascites tumor
DOSE/DURATION :
50 umol/L
REFERENCE :
PAACA3 Proceedings of the American Association for Cancer Research. (Waverly Press, 428 E. Preston St., Baltimore, MD 21202) V.1- 1954- Volume(issue)/page/year: 24,309,1983 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3180 No. of Facilities: 68 (estimated) No. of Industries: 1 No. of Occupations: 4 No. of Employees: 9321 (estimated) No. of Female Employees: 8677 (estimated)

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H350

[ Precautionary Statements ]:
P201-P280-P301 + P312 + P330-P308 + P313

[ Personal Protective Equipment ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic

[ Risk Phrases ]:
R45;R22

[ Safety Phrases ]:
S53-S45

[ RIDADR ]:
UN 3249

[ WGK Germany ]:
3

[ RTECS ]:
KC0190000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

[ HS Code ]:
2932999099

Synthetic Route

Precursor & DownStream

Precursor

  • benzyl (4-((5R,5aR,8aR,9S)-9-(((2R,4aR,6R,7R,8S,8aR)-7,8-bis(benzyloxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-6-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxyphenyl) carbonate
  • Lignan P
  • Dimethyl Acetal
  • 4'-Demethylepipodophyllotoxin
  • 4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin
  • 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4'-demethylepipodophyllotoxin
  • 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOSE

DownStream

  • Lignan P
  • 2'-chloroetoposide

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

TAp73 promotes cell survival upon genotoxic stress by inhibiting p53 activity.

Oncotarget 5(18) , 8107-22, (2014)

p53 plays a key role in regulating DNA damage response by suppressing cell cycle progression or inducing apoptosis depending on extent of DNA damage. However, it is not clear why mild genotoxic stress...

DNA damage-specific deubiquitination regulates Rad18 functions to suppress mutagenesis.

J. Cell Biol. 206(2) , 183-97, (2014)

Deoxyribonucleic acid (DNA) lesions encountered during replication are often bypassed using DNA damage tolerance (DDT) pathways to avoid prolonged fork stalling and allow for completion of DNA replica...

SK053 triggers tumor cells apoptosis by oxidative stress-mediated endoplasmic reticulum stress.

Biochem. Pharmacol. 93(4) , 418-27, (2015)

Thioredoxins (Trx) together with thioredoxin reductases (TrxR) participate in the maintenance of protein thiol homeostasis and play cytoprotective roles in tumor cells. Therefore, thioredoxin-thioredo...


More Articles


Related Compounds

  • etoposide
  • etoposide
  • etoposide
  • NPF-etoposide
  • etoposide aglycone
  • Etoposide Phosphate
  • 4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
  • 1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
  • 2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
  • 1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
  • 5-Bromo-2,4-dimethoxyphenylboronic acid
  • (4-Methyl-tetrahydro-furan-2-yl)-methanol
  • N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
  • 4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
  • tert-Butyl-DL-alanine
  • 4-amino-N-[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-N-ethylbenzenesulfonamide