Etoposide

  • CAT Number: A001070
  • CAS Number: 33419-42-0
  • Molecular Formula: C₂₂H₂₉FO₅
  • Molecular Weight: 588.56
  • Purity: ≥95%
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Etoposide is a semisynthetic derivative of podophyllotoxin and a substance extracted from the mandrake root Podophyllum peltatum. Possessing potent antineoplastic properties, etoposide binds to and inhibits topoisomerase II and its function in ligating cleaved DNA molecules, resulting in the accumulation of single- or double-strand DNA breaks, the inhibition of DNA replication and transcription, and apoptotic cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

Catalog Number A001070
CAS Number 33419-42-0
Synonyms

VePesid; Toposar; Trans-Etoposide; Lastet; (-)-Etoposide

Molecular Formula

C₂₂H₂₉FO₅

Purity 95%
Target Topoisomerase
Solubility >29.4mg/mL in DMSO
Storage -20°C
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
InChIKey VJJPUSNTGOMMGY-MRVIYFEKSA-N
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
Reference

1: Purnak S, Azar J, Mark LA. Etoposide as a single agent in the treatment of
mycosis fungoides: A retrospective analysis. Dermatol Ther. 2018 Jan 9. doi:
10.1111/dth.12586. [Epub ahead of print] PubMed PMID: 29316111.
<br>

2: Fei HR, Li ZJ, Ying-Zhang, Yue-Liu, Wang FZ. HBXIP regulates etoposide-induced
cell cycle checkpoints and apoptosis in MCF-7 human breast carcinoma cells. Gene.
2018 Jan 5. pii: S0378-1119(18)30026-X. doi: 10.1016/j.gene.2018.01.019. [Epub
ahead of print] PubMed PMID: 29309885.
<br>

3: Pantín C, Letellez J, Calzas J, Mohedano E. [Indirect identification of
hypersensitivity reaction to etoposide mediated by polysorbate 80]. Farm Hosp.
2018 Jan 1;42(1):27-28. doi: 10.7399/fh.10882. Spanish. PubMed PMID: 29306312.
<br>

4: Dittus C, Grover N, Ellsworth S, Tan X, Park SI. Bortezomib in combination
with dose-adjusted EPOCH (etoposide, prednisone, vincristine, cyclophosphamide,
and doxorubicin) induces long-term survival in patients with plasmablastic
lymphoma: a retrospective analysis. Leuk Lymphoma. 2018 Jan 5:1-7. doi:
10.1080/10428194.2017.1416365. [Epub ahead of print] PubMed PMID: 29303024.
<br>

5: Kim YA, Byun JM, Park K, Bae GH, Lee D, Kim DS, Yoon SS, Koh Y. Redefining the
role of etoposide in first-line treatment of peripheral T-cell lymphoma. Blood
Adv. 2017 Oct 27;1(24):2138-2146. doi: 10.1182/bloodadvances.2017010819.
eCollection 2017 Nov 14. PubMed PMID: 29296861; PubMed Central PMCID: PMC5737133.
<br>

6: Grafe C, Semrau S, Hein A, Beckmann MW, Mackensen A, D&#246;rje F, Fromm MF. Dose
adjustment of cisplatin, etoposide, and ifosfamide according to kidney function:
a retrospective analysis and implications for medication safety. Naunyn
Schmiedebergs Arch Pharmacol. 2018 Jan 2. doi: 10.1007/s00210-017-1456-2. [Epub
ahead of print] PubMed PMID: 29294142.
<br>

7: Mayer SA, Solimando DA, Waddell JA. Cancer Chemotherapy Update: Bevacizumab,
Etoposide, and Cisplatin Regimen for Refractory Brain Metastases. Hosp Pharm.
2017 Jun;52(6):394-399. doi: 10.1177/0018578717717622. Epub 2017 Aug 20. PubMed
PMID: 29276261; PubMed Central PMCID: PMC5735694.

<br>
8: Ferreira de Oliveira JMP, Pacheco AR, Coutinho L, Oliveira H, Pinho S, Almeida
L, Fernandes E, Santos C. Combination of etoposide and fisetin results in
anti-cancer efficiency against osteosarcoma cell models. Arch Toxicol. 2017 Dec
21. doi: 10.1007/s00204-017-2146-z. [Epub ahead of print] PubMed PMID: 29270805.
<br>

9: Ehl S. Etoposide for HLH: the limits of efficacy. Blood. 2017 Dec
21;130(25):2692-2693. doi: 10.1182/blood-2017-10-808543. PubMed PMID: 29269529.
<br>

10: Yoon S, Lee DH, Kim SW. Comments on the trial of cisplatin and etoposide plus
thoracic radiotherapy followed by nivolumab or placebo for locally advanced
non-small cell lung cancer (RTOG 3505). J Thorac Dis. 2017 Oct;9(10):3525-3528.
doi: 10.21037/jtd.2017.09.12. PubMed PMID: 29268332; PubMed Central PMCID:
PMC5723812.

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