Etoposide phosphate

  • CAT Number: R053531
  • CAS Number: 117091-64-2
  • Molecular Formula: C29H33O16P
  • Molecular Weight: 668.541
  • Purity: ≥95%
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Etoposide phosphate is a phosphate salt of a semisynthetic derivative of podophyllotoxin. Etoposide binds to the enzyme topoisomerase II, inducing double-strand DNA breaks, inhibiting DNA repair, and resulting in decreased DNA synthesis and tumor cell proliferation. Cells in the S and G2 phases of the cell cycle are most sensitive to this agent.

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 CC1OCC2C(O1)C(C(C(O2)OC3C4COC(=O)C4C(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

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