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.
CAS 117091-64-2 MFCD00270859
化学结构图
SMILES: COc1cc([C@@H]2c3cc4c(cc3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1OP(=O)(O)O
化学属性
| Mol. Formula | C29H33O16P |
|---|---|
| Mol. Weight | 668.54 |
| Appearance | Solid powder |
| Solubility | Soluble in DMSO, not in water |
别名和识别编码
| Chemical Name | 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. |
|---|---|
| CAS Number | 117091-64-2 |
| Synonym | ######## Eposin Etopophos Vepesid VP16. US brand name: Etopophos. Abbreviation: ETOP. |
| Chemical Name Translation | |
| Formula | C29H33O16P |
| 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 |
| InChIKey | LIQODXNTTZAGID-OCBXBXKTSA-N |
| 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 |
| Canonical SMILES | O=P(O)(OC1=C(OC)C=C([C@H](C2=C3C=C4OCOC4=C2)[C@@]5([H])C(OC[C@]5([H])[C@@H]3O[C@H]6[C@H](O)[C@@H](O)[C@]7([H])O[C@H](C)OC[C@@]7([H])O6)=O)C=C1OC)O |
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分类
- Carbohydrates & Derivatives
- Drug Analogues
- Heterocycles
- Inhibitors
- Pharmaceuticals
- Intermediates & Fine Chemicals,
产品应用
- 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.
相关文献及参考
- Kaul, S. et al.: J. Clin. Pharmacol., 13, 2835 (1995); J. Pharmakin. Biopharmac., 24, 313 (1996); Brooks, D.J. et al.: Anti-Cancer Drugs, 6, 637 (1995);
