Determine the necessary mass, volume, or concentration for preparing a solution.
Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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SKU | Size | Availability | Price | Qty |
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E121713-100mg | 100mg | In stock | $39.90 | |
E121713-250mg | 250mg | In stock | $59.90 | |
E121713-500mg | 500mg | In stock | $99.90 | |
E121713-1g | 1g | In stock | $169.90 | |
E121713-5g | 5g | In stock | $589.90 |
Topoisomerase II inhibitor
Synonyms | VP-16-213 | 4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-beta-D-glucopyranoside) | ETOPOSIDE [HSDB] | ETOPOSIDE [IARC] | (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- |
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Specifications & Purity | Moligand™, ≥98% |
Biochemical and Physiological Mechanisms | Etoposide is an antitumor agent that complexes with topoisomerase II and DNA to enhance double-strand and single-strand cleavage of DNA and reversibly inhibit religation. Blocks the cell cycle in in S-phase and G2-phase of the cell cycle; induces apoptosi |
Storage Temp | Protected from light,Store at -20°C |
Shipped In | Ice chest + Ice pads |
Grade | Moligand™ |
Action Type | INHIBITOR |
Mechanism of action | DNA topoisomerase II inhibitor |
Note | Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details. |
Product Description | Etoposide is an antitumor agent that complexes with topoisomerase II and DNA to enhance double-strand and single-strand cleavage of DNA and reversibly inhibit religation. Blocks the cell cycle in in S-phase and G2-phase of the cell cycle; induces apoptosis in normal and tumor cell lines; inhibits synthesis of the oncoprotein Mdm2 and induces apoptosis in tumor lines that overexpress Mdm2. product description: Etoposide is synthesised from podophyllotoxins of plants. |
ALogP | 0.6 |
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Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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IUPAC Name | (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 |
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INCHI | 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 |
InChi Key | VJJPUSNTGOMMGY-MRVIYFEKSA-N |
Canonical SMILES | CC1OCC2C(O1)C(C(C(O2)OC3C4COC(=O)C4C(C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O |
Isomeric SMILES | C[C@@H]1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)O[C@H]3[C@H]4COC(=O)[C@@H]4[C@@H](C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O |
WGK Germany | 3 |
RTECS | KC0190000 |
PubChem CID | 36462 |
Molecular Weight | 588.56 |
Reaxy-Rn | 365969 |
DrugBank Ligand | DB00773 |
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PubChem CID | 36462 |
CAS Registry No. | 33419-42-0 |
ChEMBL Ligand | CHEMBL44657 |
Wikipedia | Etoposide |
ChEBI | CHEBI:4911 |
RCSB PDB Ligand | EVP |
DrugCentral Ligand | 1112 |
Enter Lot Number to search for COA:
Find and download the COA for your product by matching the lot number on the packaging.
Lot Number | Certificate Type | Date | Item |
---|---|---|---|
C2111192 | Certificate of Analysis | Dec 04, 2024 | E121713 |
C2111193 | Certificate of Analysis | Dec 04, 2024 | E121713 |
E1922217 | Certificate of Analysis | Mar 09, 2023 | E121713 |
K2208137 | Certificate of Analysis | Aug 17, 2022 | E121713 |
K2208142 | Certificate of Analysis | Aug 17, 2022 | E121713 |
K2208143 | Certificate of Analysis | Aug 17, 2022 | E121713 |
K2208144 | Certificate of Analysis | Aug 17, 2022 | E121713 |
K2208145 | Certificate of Analysis | Aug 17, 2022 | E121713 |
K2420152 | Certificate of Analysis | Aug 17, 2022 | E121713 |
Solubility | Soluble in DMSO (30 mg/ml), dimethyl formamide, ethyl ether, chloroform:methanol (1:1), methanol (slightly), acetone (slightly), water (<1 mg/ml) at 25 °C, and ethanol (<1 mg/ml) at 25 °C. |
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Sensitivity | light sensitive |
Specific Rotation[α] | -110.5° (C=0.6,CHCl3) |
Melt Point(°C) | 251°C |
Pictogram(s) | GHS08, GHS07 |
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Signal | Danger |
Hazard Statements | H302:Harmful if swallowed H350:May cause cancer |
Precautionary Statements | P280:Wear protective gloves/protective clothing/eye protection/face protection. P405:Store locked up. P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P270:Do not eat, drink or smoke when using this product. P330:Rinse mouth. P203:Obtain, read and follow all safety instructions before use. P301+P317:IF SWALLOWED: Get medical help. P318:if exposed or concerned, get medical advice. |
WGK Germany | 3 |
RTECS | KC0190000 |
Reaxy-Rn | 365969 |
Merck Index | 3886 |
Starting at $45.90
1. Zhuangzhuang Li, Baoyan Ding, Mustafa R. K. Ali, Lizhen Zhao, Xiaoling Zang, Zhihua Lv. (2022) Dual Effect of Tryptamine on Prostate Cancer Cell Growth Regulation: A Pilot Study. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 23 (19): (11087). [PMID:36232383] [10.3390/ijms231911087] |
2. Ma Xiaojing, Wang Tong, Yu Zequan, Shao Junqian, Chu Jun, Zhu Huixia, Yao Risheng. (2022) Formulation and Physicochemical and Biological Characterization of Etoposide-Loaded Submicron Emulsions with Biosurfactant of Sophorolipids. AAPS PHARMSCITECH, 23 (6): (1-13). [PMID:35773548] [10.1208/s12249-022-02329-2] |
3. Wang Xiao, Xu Na, Li Qinglin, Chen Shengqi, Cheng Hui, Yang Mo, Jiang Ting, Chu Jun, Ma Xiaojing, Yin Dengke. (2021) Lactonic sophorolipid–induced apoptosis in human HepG2 cells through the Caspase-3 pathway. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 105 (5): (2033-2042). [PMID:33582833] [10.1007/s00253-020-11045-5] |
4. Meifang Cai, Caiping Ding, Xuanyu Cao, Fangfang Wang, Cuiling Zhang, Yuezhong Xian. (2019) Label-free fluorometric assay for cytochrome c in apoptotic cells based on near infrared Ag2S quantum dots. ANALYTICA CHIMICA ACTA, 1056 (153). [PMID:30797456] [10.1016/j.aca.2019.01.005] |
5. Jingwei Wang, Zhiheng Guo, Jianxin Xiong, Datong Wu, Shan Li, Yongxin Tao, Yong Qin, Yong Kong. (2019) Facile synthesis of chitosan-grafted beta-cyclodextrin for stimuli-responsive drug delivery. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 125 (941). [PMID:30572042] [10.1016/j.ijbiomac.2018.12.150] |
6. Xiaolin Liu, Yongxin Tao, Huihui Mao, Yong Kong, Jian Shen, Linhong Deng, Linsong Yang. (2017) Construction of magnetic-targeted and NIR irradiation-controlled drug delivery platform with Fe3O4@Au@SiO2 nanospheres. CERAMICS INTERNATIONAL, 43 (5061). [PMID:] [10.1016/j.ceramint.2017.01.017] |
7. Junling Wang, Ran Wang, Fangrong Zhang, Yajun Yin, Leixia Mei, Fengjuan Song, Mingtao Tao, Wanqing Yue, Wenying Zhong. (2016) Overcoming multidrug resistance by a combination of chemotherapy and photothermal therapy mediated by carbon nanohorns. Journal of Materials Chemistry B, 4 (36): (6043-6051). [PMID:32263493] [10.1039/C6TB01469K] |
8. Lian Chen, Hengmin Cui, Jing Fang, Huidan Deng, Ping Kuang, Hongrui Guo, Xun Wang, Ling Zhao. (2016) Glutamine deprivation plus BPTES alters etoposide- and cisplatin-induced apoptosis in triple negative breast cancer cells. Oncotarget, 7 (34): ( 54691–54701). [PMID:27419628] [10.18632/oncotarget.10579] |
9. Yadong Tang,Boxin Huang,Yuqin Dong,Wenlong Wang,Xi Zheng,Wei Zhou,Kun Zhang,Zhiyun Du. (2017-06-07) Three-dimensional prostate tumor model based on a hyaluronic acid-alginate hydrogel for evaluation of anti-cancer drug efficacy.. Journal of biomaterials science. Polymer edition, 28 ((14)): (1603-1616). [PMID:28583017] |
1. Lammert CR et al.. (2020) AIM2 inflammasome surveillance of DNA damage shapes neurodevelopment.. Nature, 580 (7805): (647-652). [PMID:32350463] |
2. Tian R et al.. (2019) CRISPR Interference-Based Platform for Multimodal Genetic Screens in Human iPSC-Derived Neurons.. Neuron, 104 (2): (239-255.e12). [PMID:31422865] |
3. Saliou B et al.. (2013) Development and in vitro evaluation of a novel lipid nanocapsule formulation of etoposide.. Eur J Pharm Sci, 50 (2): (172-80). [PMID:23831519] |
4. Sultana S & Bishayi B. (2020) Etoposide-mediated depletion of peripheral blood monocytes post s.aureus infection attenuates septic arthritis by modulating macrophage-derived factors responsible for inflammatory destruction.. Immunol Lett, 220 (51-62). [PMID:32032616] |
5. Hijaze N et al.. (2020) Inducing regulated necrosis and shifting macrophage polarization with anti-EMMPRIN antibody (161-pAb) and complement factors.. J Leukoc Biol, [PMID:33205451] |
6. Moretti FA et al.. (2021) Metabolite and thymocyte development defects in ADA-SCID mice receiving enzyme replacement therapy.. Sci Rep, 11 (23221). [PMID:34853379] |
7. Ulrich G et al.. (2018) Phosphorylation of nuclear Tau is modulated by distinct cellular pathways.. Sci Rep, 8 (17702). [PMID:30531974] |
8. Sola M et al.. (2020) Tau affects P53 function and cell fate during the DNA damage response.. Commun Biol, 3 (245). [PMID:32427887] |
9. Hu Q et al.. (2020) The ARK Assay Is a Sensitive and Versatile Method for the Global Detection of DNA-Protein Crosslinks.. Cell Rep, 30 (4): (1235-1245.e4). [PMID:31995761] |
10. Zhuangzhuang Li, Baoyan Ding, Mustafa R. K. Ali, Lizhen Zhao, Xiaoling Zang, Zhihua Lv. (2022) Dual Effect of Tryptamine on Prostate Cancer Cell Growth Regulation: A Pilot Study. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 23 (19): (11087). [PMID:36232383] [10.3390/ijms231911087] |
11. Ma Xiaojing, Wang Tong, Yu Zequan, Shao Junqian, Chu Jun, Zhu Huixia, Yao Risheng. (2022) Formulation and Physicochemical and Biological Characterization of Etoposide-Loaded Submicron Emulsions with Biosurfactant of Sophorolipids. AAPS PHARMSCITECH, 23 (6): (1-13). [PMID:35773548] [10.1208/s12249-022-02329-2] |
12. Wang Xiao, Xu Na, Li Qinglin, Chen Shengqi, Cheng Hui, Yang Mo, Jiang Ting, Chu Jun, Ma Xiaojing, Yin Dengke. (2021) Lactonic sophorolipid–induced apoptosis in human HepG2 cells through the Caspase-3 pathway. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 105 (5): (2033-2042). [PMID:33582833] [10.1007/s00253-020-11045-5] |
13. Meifang Cai, Caiping Ding, Xuanyu Cao, Fangfang Wang, Cuiling Zhang, Yuezhong Xian. (2019) Label-free fluorometric assay for cytochrome c in apoptotic cells based on near infrared Ag2S quantum dots. ANALYTICA CHIMICA ACTA, 1056 (153). [PMID:30797456] [10.1016/j.aca.2019.01.005] |
14. Jingwei Wang, Zhiheng Guo, Jianxin Xiong, Datong Wu, Shan Li, Yongxin Tao, Yong Qin, Yong Kong. (2019) Facile synthesis of chitosan-grafted beta-cyclodextrin for stimuli-responsive drug delivery. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 125 (941). [PMID:30572042] [10.1016/j.ijbiomac.2018.12.150] |
15. Xiaolin Liu, Yongxin Tao, Huihui Mao, Yong Kong, Jian Shen, Linhong Deng, Linsong Yang. (2017) Construction of magnetic-targeted and NIR irradiation-controlled drug delivery platform with Fe3O4@Au@SiO2 nanospheres. CERAMICS INTERNATIONAL, 43 (5061). [PMID:] [10.1016/j.ceramint.2017.01.017] |
16. Junling Wang, Ran Wang, Fangrong Zhang, Yajun Yin, Leixia Mei, Fengjuan Song, Mingtao Tao, Wanqing Yue, Wenying Zhong. (2016) Overcoming multidrug resistance by a combination of chemotherapy and photothermal therapy mediated by carbon nanohorns. Journal of Materials Chemistry B, 4 (36): (6043-6051). [PMID:32263493] [10.1039/C6TB01469K] |
17. Lian Chen, Hengmin Cui, Jing Fang, Huidan Deng, Ping Kuang, Hongrui Guo, Xun Wang, Ling Zhao. (2016) Glutamine deprivation plus BPTES alters etoposide- and cisplatin-induced apoptosis in triple negative breast cancer cells. Oncotarget, 7 (34): ( 54691–54701). [PMID:27419628] [10.18632/oncotarget.10579] |
18. Yadong Tang,Boxin Huang,Yuqin Dong,Wenlong Wang,Xi Zheng,Wei Zhou,Kun Zhang,Zhiyun Du. (2017-06-07) Three-dimensional prostate tumor model based on a hyaluronic acid-alginate hydrogel for evaluation of anti-cancer drug efficacy.. Journal of biomaterials science. Polymer edition, 28 ((14)): (1603-1616). [PMID:28583017] |