For research use only. Not for therapeutic Use.
Etoposide Phosphate（Cat No.:R053531）is a water-soluble prodrug of etoposide, a topoisomerase II inhibitor used in chemotherapy. It prevents the re-ligation of DNA strands during replication, causing DNA damage and leading to apoptosis in rapidly dividing cancer cells. Etoposide Phosphate is favored over etoposide due to its enhanced solubility and easier administration, particularly for patients unable to tolerate oral formulations. It is commonly used to treat cancers such as small-cell lung cancer, testicular cancer, and lymphomas. Its efficacy and versatility make it an essential component of cancer treatment regimens.
| Catalog Number | R053531 |
| CAS Number | 117091-64-2 |
| Synonyms | [5R-[5α,5aβ,8aα,9β(R*)]]-5-[3,5-Dimethoxy-4-(phosphonooxy)phenyl]-9-[(4,6-O-ethylidene-β-D-glucopyranosyl)oxy]-5,8,8a,9-tetrahydrofuro[3’,4’:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; BMY 40481; Etopofos; Etopophos; Etoposide 4’-Phosphate; (5R,5aR |
| Molecular Formula | C29H33O16P |
| Purity | ≥95% |
| Storage | Store at -20°C |
| IUPAC Name | [4-[(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]-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]-2,6-dimethoxyphenyl] dihydrogen phosphate |
| InChI | InChI=1S/C29H33O16P/c1-11-38-9-20-27(42-11)23(30)24(31)29(43-20)44-25-14-7-17-16(40-10-41-17)6-13(14)21(22-15(25)8-39-28(22)32)12-4-18(36-2)26(19(5-12)37-3)45-46(33,34)35/h4-7,11,15,20-25,27,29-31H,8-10H2,1-3H3,(H2,33,34,35)/t11-,15+,20-,21-,22+,23-,24-,25-,27-,29+/m1/s1 |
| InChIKey | LIQODXNTTZAGID-OCBXBXKTSA-N |
| 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)OP(=O)(O)O)OC)O)O |
| Reference | </br>1:Dose escalation study to evaluate safety, tolerability and efficacy of intravenous etoposide phosphate administration in 27 dogs with multicentric lymphoma. Boyé P, Serres F, Marescaux L, Hordeaux J, Bouchaert E, Gomes B, Tierny D.PLoS One. 2017 May 15;12(5):e0177486. doi: 10.1371/journal.pone.0177486. eCollection 2017. PMID: 28505195 Free Article</br>2:Preclinical Acute Ocular Safety Study of Combined Intravitreal Carboplatin and Etoposide Phosphate for Retinoblastoma. Mohney BG, Elner VM, Smith AB, Harbour JW, Smith BD, Musch DC, Smith SJ.Ophthalmic Surg Lasers Imaging Retina. 2017 Feb 1;48(2):151-159. doi: 10.3928/23258160-20170130-09. PMID: 28195618 </br>3:Etoposide phosphate hypersensitivity overcome using a desensitisation programme enabling optimal therapy for relapsed Hodgkin lymphoma. Polistena P, Tran Q, Cirillo M, O/’Sullivan M, Purtill D.Bone Marrow Transplant. 2017 Mar;52(3):455-456. doi: 10.1038/bmt.2016.288. Epub 2016 Oct 31. No abstract available. PMID: 27797366 </br>4:Transdermal Delivery of Etoposide Phosphate I: In Vitro and In Vivo Evaluation. Patel H, Joshi A, Joshi A, Stagni G.J Pharm Sci. 2016 Jul;105(7):2114-22. doi: 10.1016/j.xphs.2016.04.014. Epub 2016 May 25. PMID: 27233689 </br>5:Transdermal Delivery of Etoposide Phosphate II: In Vitro In Vivo Correlations (IVIVC). Patel H, Joshi A, Joshi A, Stagni G.J Pharm Sci. 2016 Jul;105(7):2139-45. doi: 10.1016/j.xphs.2016.04.022. Epub 2016 May 25. PMID: 27233686 </br>6:Theranostic etoposide phosphate/indium nanoparticles for cancer therapy and imaging. Srinivas R, Satterlee A, Wang Y, Zhang Y, Wang Y, Huang L.Nanoscale. 2015 Nov 28;7(44):18542-51. doi: 10.1039/c5nr04509f. Epub 2015 Oct 22. PMID: 26489694 Free PMC Article</br>7:Successful Treatment with Etoposide Base after an Acute Hypersensitivity Reaction to Etoposide Phosphate. Leguay Z, Bourneau-Martin D, Pellier I, Le Louet H, Drablier G, Lagarce L, Lainé-Cessac P.Pediatr Blood Cancer. 2016 Mar;63(3):571. doi: 10.1002/pbc.25797. Epub 2015 Oct 15. No abstract available. PMID: 26468691 </br>8:Hypersensitivity reactions to etoposide phosphate. Sambasivan K, Mahmoud S, Kokache A, Seckl M, Savage P.J Oncol Pharm Pract. 2014 Apr;20(2):158-60. doi: 10.1177/1078155213488015. Epub 2013 Jun 4. PMID: 23740378 </br>9:Etoposide phosphate enhances the acetylation level of translation elongation factor 1A in PLC5 cells. Hu JL, Xu G, Lei L, Zhang WL, Hu Y, Huang AL, Cai XF.Z Naturforsch C. 2012 May-Jun;67(5-6):327-30. PMID: 22888539 </br>10:Anaphylactic reaction to etoposide phosphate. Lindsay H, Gaynon P.Pediatr Blood Cancer. 2012 Oct;59(4):765. doi: 10.1002/pbc.24183. Epub 2012 Apr 22. No abstract available. PMID: 22522419 |
