An inhibitor of topoisomerase II
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Labeled Version(s)
26488Etoposide-d3
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Etoposide

Item No. 12092

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5aR)-9S-[[4,6-O-ethylidene-β-D-glucopyranosyl]oxy]-5R,8,8aR,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-furo[3',4':6,7]naphtho[2,3-d]-1R,3-dioxol-6(5aH)-one
CAS Number
33419-42-0
Synonyms
  • EPE
  • NSC 141540
  • VP-16-123
Molecular Formula
C29H32O13
Formula Weight
588.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.5 mg/mlDMSO: 10 mg/mlDMSO:PBS (pH 7.2)(1:5): 0.1 mg/ml
λmax
206, 283 nm
SMILES
O=C1[C@]2([H])[C@H](C3=CC(OC)=C(O)C(OC)=C3)C(C=C(OCO4)C4=C5)=C5[C@@H](O[C@]6([H])O[C@@](CO[C@@H](C)O7)([H])[C@]7([H])[C@H](O)[C@H]6O)[C@@]2([H])CO1
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $28

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    50 mg

    $39

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    100 mg

    $72

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    500 mg

    $220

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    Cayman Chemical
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    Product Description

    Etoposide is a plant alkaloid and an inhibitor of topoisomerase II (IC50 = 60.3 μM).1,2 It inhibits proliferation of a variety of adenocarcinoma cells (IC50s = 0.005-12,200 µM) and human umbilical vein endothelial (HUVEC) cells (IC50 = 0.249 µM).3 It reduces tumor growth in an Ma human embryonal carcinoma mouse xenograft model when administered at a dose of 25 mg/kg, an effect that is enhanced by concomitant administration of the immunosuppressant cyclosporin A (Item No. 12088).4 Etoposide also inhibits nuclear receptor coactivator 3 (IC50 = 2.48 µM).5 Formulations containing etoposide have been used in combination therapy in the treatment of cancer.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chen, G.L., Yang, L., Rowe, T.C., et al. Nonintercalative antitumor drugs interfere with the breakage-reunion reaction of mammalian DNA topoisomerase II. The Journal of Biological Chemisty 259(21), 13560-13566 (1984).

    2. Wu, W.B., Ou, J.B., Huang, Z.H., et al. Synthesis and evaluation of mansonone F derivatives as topoisomerase inhibitors. Eur. J. Med. Chem. 46(8), 3339-3347 (2011).

    3. Drevs, J., Fakler, J., Eisele, S., et al. Antiangiogenic potency of various chemotherapeutic drugs for metronomic chemotherapy. Anticancer Res. 24, 1759-1764 (2004).

    4. Osieka, R., Seeber, S., Pannenbäcker, R., et al. Enhancement of etoposide-induced cytotoxicity by cyclosporin A. Cancer Chemother. Pharmacol. 18(3), 198-202 (1986).

    5. O'Malley, B. Luminescence-based cell-based high throughput dose response assay for inhibitors of the Steroid Receptor Coactivator 3 (SRC;NCOA3) - BioAssay summary.

    Product Citations

    Huang, J.J., Corona, A.L., Dunn, B.P., et al. Increased type III TGF-β receptor shedding decreases tumorigenesis through induction of epithelial-to-mesenchymal transition. Oncogene 38(18), 3402-3414 (2019).

    Fuhrmann-Stroissnigg, H., Ling, Y.Y., Zhao, J., et al. Identification of HSP90 inhibitors as a novel class of senolytics. Nat. Commun. 8(1), 422 (2017).

    Bosnakovski, D., Choi, S.H., Strasser, J.M., et al. High-throughput screening identifies inhibitors of DUX4-induced myoblast toxicity. Skelet. Muscle 4(4), (2014).