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CAS No. :	33419-42-0
Formula :	C₂₉H₃₂O₁₃
M.W :	588.56
SMILES Code :	O=C1OC[C@]2([H])[C@H](O[C@H]3[C@@H]([C@H]([C@@H]4O[C@H](C)OC[C@H]4O3)O)O)C5=C(C=C6OCOC6=C5)[C@@H](C7=CC(OC)=C(O)C(OC)=C7)[C@]21[H]
Synonyms :	VP-16; VP-16-213; NSC 141540
MDL No. :	MFCD00869325
InChI Key :	VJJPUSNTGOMMGY-MRVIYFEKSA-N
Pubchem ID :	36462

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335-H351-H361
Precautionary Statements:	P261-P305+P351+P338

Description	Etoposide (VP-16; VP-16-213) is an anticancer chemotherapeutic agent. It functions by inhibiting topoisomerase II, thereby halting DNA replication. Etoposide induces cell cycle arrest, apoptosis, and autophagy [1].
Target	Topo II

MCF7/VP cells	5 μM	18 h	To evaluate the sensitivity of MCF7/VP cells to etoposide, results showed that CBLC4H10, CBLC4E10, and CBLC4E11 increased the sensitivity of cells to etoposide by 11.6-fold, 6.8-fold, and 7.7-fold, respectively	PMC2746061
U2OS cells	68 μM	24 h	To investigate the effect of RSF1 deficiency on etoposide-induced cell death, results showed that RSF1 deficiency significantly reduced cell death.	PMC6197202
H1048 and H69 cells	1 µM	Not mentioned	To investigate the anticancer efficacy of Etoposide in combination with Silibinin and Cisplatin on small cell lung cancer (SCLC) cells	PMC9532437
HeLa cells	50 µM	2 h	Induced TOP2-DNA crosslinks and monitored SPRTN autocleavage	PMC9867749
HeLa cells	100 µM		Etoposide was used to induce cell death, and the results showed that it could cause apoptosis.	PMC2193790
TC-32 cells	7.2 nM	2–8 h	To investigate the effect of Etoposide on MRP-1 expression in TC-32 cells, results showed that Etoposide increased MRP-1 expression in the plasma membrane and mitochondria.	PMC3304412
TC-32MRP-1.Fb-neo cells	7–240 nM	48 h	To investigate the effect of Etoposide on the viability of TC-32MRP-1.Fb-neo cells, results showed that Etoposide significantly increased drug resistance in these cells.	PMC3304412
H1299 cells	50 μM	24 hours	To evaluate the effect of Pin1 on p53NLS-induced transcription-independent apoptosis, results showed that Pin1 co-expression significantly increased apoptosis induced by p53NLS.	PMC3554345

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CAS No.: 33419-42-0

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CAS No.: 33419-42-0

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mice	TKO mouse model	intraperitoneal injection	15 mg/kg	on days 2 and 4	To evaluate the therapeutic effect of etoposide on tumors in TKO mice, results showed that etoposide increased tumor cell apoptosis and the proportion of Hes1-positive cells	PMC5776014
Mice	Neuroblastoma model	Intraperitoneal injection	6 mg/kg	Once daily for 5 consecutive days	To evaluate the efficacy of etoposide in the neuroblastoma model, results showed that the combination of Reversan with etoposide significantly prolonged the survival time of mice compared to etoposide alone	PMC2746061
Mice	4T1 breast cancer model	Intraperitoneal injection	5 mg/kg	Administered on day 7 and 12	To evaluate the effect of Etoposide on MDSC, results showed that Etoposide had limited effects on MDSC depletion	PMC3896092
Mice	Rsf1 conditional knockout mice	Intraperitoneal injection	4 mg/kg	Single dose, embryos treated at E15.0	To investigate the effect of Rsf1 deficiency on etoposide-induced DNA damage and apoptosis, results showed that Rsf1 deficiency significantly reduced apoptosis.	PMC6197202
BALB/c nude mice	Human small cell lung cancer (SCLC) xenograft model	Intraperitoneal injection	12 mg/kg	Once daily for 3 days	To investigate the anticancer efficacy of Etoposide in combination with Silibinin and Cisplatin on small cell lung cancer (SCLC) xenograft models	PMC9532437
Nude mice	SCLC subcutaneous tumor model	Intraperitoneal injection	4 mg/kg	Once every 2 days	To evaluate the antitumor effect of Etoposide on the SCLC subcutaneous tumor model, the results showed that Etoposide significantly inhibited tumor growth	PMC7150483

NCT02179528	Small Cell Lung Cancer Extensi... More >>ve Stage Less <<	PHASE2	UNKNOWN	2025-09-17	Beijing Cancer Hospital, Beiji... More >>ng, Beijing, 100042, China Less <<
NCT00000807	Sarcoma, Kaposi\|HIV Infections	PHASE2	COMPLETED	2000-07-01	Univ of Alabama at Birmingham,... More >> Birmingham, Alabama, 35294, United States\|K Norris Cancer Hosp / Los Angeles County - USC Med Ctr, Los Angeles, California, 900331079, United States\|Univ of Southern California / LA County USC Med Ctr, Los Angeles, California, 900331079, United States\|San Francisco Gen Hosp, San Francisco, California, 941102859, United States\|Denver Dept of Health and Hosps, Denver, Colorado, 80262, United States\|Univ of Colorado Health Sciences Ctr, Denver, Colorado, 80262, United States\|Yale Univ / New Haven, New Haven, Connecticut, 065102483, United States\|Univ of Miami School of Medicine, Miami, Florida, 331361013, United States\|Northwestern Univ Med School, Chicago, Illinois, 60611, United States\|Indiana Univ Hosp, Indianapolis, Indiana, 462025250, United States\|Boston Med Ctr, Boston, Massachusetts, 02118, United States\|Adirondack Med Ctr at Saranac Lake, Albany, New York, 122083479, United States\|Albany Med College / Division of HIV Medicine A158, Albany, New York, 122083479, United States\|Mid - Hudson Care Ctr, Albany, New York, 122083479, United States\|SUNY / Erie County Med Ctr at Buffalo, Buffalo, New York, 14215, United States\|City Hosp Ctr at Elmhurst / Mount Sinai Hosp, Elmhurst, New York, 11373, United States\|Saint Clare's Hosp and Health Ctr, New York, New York, 10019, United States\|Mount Sinai Med Ctr, New York, New York, 10029, United States\|Columbia Presbyterian Med Ctr, New York, New York, 100323784, United States\|Julio Arroyo, West Columbia, South Carolina, 29169, United States Less <<
NCT04356690	COVID-19	PHASE2	TERMINATED	2022-07-01	Boston Medical Center, Boston,... More >> Massachusetts, 02118, United States Less <<
NCT04804007	Germ Cell Tumor\|Non-seminomato... More >>us Germ Cell Tumor\|Ovarian Germ Cell Tumor Less <<	PHASE2	RECRUITING	2025-12-28	Indiana University Melvin & Br... More >>en Simon Cancer Center, Indianapolis, Indiana, 46202, United States Less <<
NCT01492556	Breast Cancer	PHASE2	UNKNOWN	2025-06-15	Beijing Hospital of the Minist... More >>ry of Health, Beijing, Beijing, 100005, China\|Peking Union Medical College Hospital, Beijing, Beijing, 100005, China\|Beijing Chao-yang Hospital, Beijing, Beijing, 100020, China\|Cancer Institute and Hospital, Chinese Academy of Medical Sciences, Beijing, Beijing, 100021, China\|China-Japan Friendship Hospital, Beijing, Beijing, 100029, China\|Peking University Cancer Hospital, Beijing, Beijing, 100142, China\|Guangxi Cancer Hospital, Nanning, Guangxi, 530021, China\|Harbin Medical University Cancer Hospital, Harbin, Heilongjiang, 150081, China\|Henan Cancer Hospital, Zhengzhou, Henan, 450008, China\|First Affiliated Hospital of Dalian Medical University, Dalian, Liaoning, 116011, China\|International Peace Maternity & Child Health Hospital of the China Welfare Institute, Shanghai, Shanghai, 200030, China\|Shanghai Putuo District Center Hospital, Shanghai, Shanghai, 200062, China\|Affiliated Cancer Hospital of Xinjiang Medical University, Urumqi, Xinjiang, 830011, China\|Zhejiang Cancer Hospital, Hangzhou, Zhejiang, 310022, China Less <<
NCT00000660	Sarcoma, Kaposi\|HIV Infections	PHASE1	COMPLETED	1992-07-01	San Francisco Gen Hosp, San Fr... More >>ancisco, California, 941102859, United States\|Bellevue Hosp / New York Univ Med Ctr, New York, New York, 10016, United States\|Mem Sloan - Kettering Cancer Ctr, New York, New York, 10021, United States\|Saint Luke's - Roosevelt Hosp Ctr, New York, New York, 10025, United States\|Univ of Rochester Medical Center, Rochester, New York, 14642, United States\|Julio Arroyo, West Columbia, South Carolina, 29169, United States Less <<

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
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P251	Pressurized container: Do not pierce or burn, even after use.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
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P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
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P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
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P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
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P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed