Etoposide

Modify Date: 2024-01-02 11:27:02

Etoposide Structure
Etoposide structure
 Common Name Etoposide
CAS Number 33419-42-0 Molecular Weight 588.557
Density 1.6±0.1 g/cm3 Boiling Point 798.1±60.0 °C at 760 mmHg
Molecular Formula C29H32O13 Melting Point 236-251ºC
MSDS USA Flash Point 263.6±26.4 °C
Symbol GHS07 GHS08
GHS07, GHS08		 Signal Word Danger

 Use of Etoposide


Etoposide is a chemotherapy medication used for the treatments of a number of types of cancer. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA.

 Names

Name etoposide
Synonym More Synonyms

 Etoposide Biological Activity

Description Etoposide is a chemotherapy medication used for the treatments of a number of types of cancer. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA.
Related Catalog
Target

Topoisomerase II

In Vitro Etoposide is capable of causing cytotoxicity on pancreatic β-cells by inducing apoptosis through the JNK/ERK-mediated GSK-3 downstream-triggered mitochondria-dependent signaling pathway in RIN-m5F cells[1]. Etoposide and Bevacizumab significantly abolish P1 sphere-forming ability, an effect associated with apoptosis of this subset of cells[2].
In Vivo Etoposide (50 μM) and Bevacizumab-treated hypoxic cells injected intravenously into immunodeficient mice reveals a reduced capacity to induce lung colonies, which also appear with a longer latency period[2]. Etoposide (10 mg/kg/day, i.v.) with ifosfamide and carboplatin, reduces the tumor volume in the hepatoblastoma cell injected NMRI nude mice[3].
Kinase Assay RIN-m5F cells are seeded and treated with Etoposide (10-50 μM) in the absence or presence of Z-DEVD-FMK (20 μM). At the end of treatments (for 24 h), the cell lysates are incubated at 37°C with 10 μM Ac-DEVD-AMC, a caspase-3/CPP32 substrate, for 1 h. The fluorescence of the cleaved substrate is measured by a spectrofluorometer with an excitation wavelength at 380 nm and an emission wavelength at 460 nm. Protein levels of cell lysate samples are determined using the bicinchoninic acid protein assay kit with an absorption band of 570 nm to normalize the cell numbers between control and etoposide-treated groups.
Cell Assay RIN-m5F cell is a rat pancreatic β-cell line, and cultured in a humidified chamber with a 5% CO2-95% air mixture at 37°C and maintained in RPIM 1640 medium supplemented with 10% fetal bovine serum (FBS) and antibiotics (100 U/mL of penicillin and 100 μg/mL of streptomycin). RIN-m5F cells are seeded (2 × 104 cells/well) in 96-well plates and allowed to adhere and recover overnight. The cells are changed to fresh media and then incubated with Etoposide (1-100 μM) in the absence or presence of the pharmacological inhibitors (lithium chloride (LiCl)-50 μM; SP600125-20 μM; PD98059-20 μM) for 24 h.
Animal Admin The in vivo model for nude mice HB (NMHB) has been established. Only HB cells with embryonal components are grafted and reproduced successfully in this model. Each NMHB subsequently is transplanted into 50 mice for treatment groups. Treatment is initiated when the majority of the tumors reach a volume of 50-100 mm3. The mice are stratified according to their tumor volume and randomLy assigned to groups of ten animals each. The animals injected with tumor are given ifosfamide, cisplatin, doxorubicin, etoposide (10 mg/kg/day, i.v.), and carboplatin as single agents in two blocks. One group of ten animals for each original xenograft served as a control group. After initiation of treatment, the tumor growth is recorded at 5-day intervals for 25-30 days and the relative tumor volumes are calculated. Twenty-four hours before the animals are sacrificed, bromodeoxyuridine (BrdU) is injected intraperitoneally for the semiquantitative determination of proliferation activity of the tumor cells (50 μg of BrdU/g body weight).
References

[1]. Lee KI, et al. Etoposide induces pancreatic β-cells cytotoxicity via the JNK/ERK/GSK-3 signaling-mediated mitochondria-dependent apoptosis pathway. Toxicol In Vitro. 2016 Jul 26. pii: S0887-2333(16)30147-3.

[2]. Calvani M, det al. Etoposide-Bevacizumab a new strategy against human melanoma cells expressing stem-like traits. Oncotarget. 2016 Jun 9. doi: 10.18632/oncotarget.9939.

[3]. Fuchs, J., et al. Comparative activity of cisplatin, ifosfamide, doxorubicin, carboplatin, and etoposide in heterotransplanted hepatoblastoma. Cancer, 1998. 83(11): p. 2400-7.

 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

 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
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

 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%

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 Synonyms

(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
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