Annamycin is a semi-synthetic doxorubicin analogue annamycin with antineoplastic activity. Annamycin intercalates into DNA and inhibits topoisomerase II, resulting in the inhibition of DNA replication and repair and RNA and protein synthesis. This agent circumvents multidrug-resistance (MDR) transporters, including P-glycoprotein (P-gp).
CAS 92689-49-1 MFCD00914599
化学结构图
SMILES: C[C@@H]1O[C@@H](O[C@H]2C[C@](O)(C(=O)CO)Cc3c(O)c4c(c(O)c32)C(=O)c2ccccc2C4=O)[C@H](I)[C@H](O)[C@H]1O
化学属性
| Mol. Formula | C26H25IO11 |
|---|---|
| Mol. Weight | 640.37 |
| Appearance | Solid powder |
| Solubility | Soluble in DMSO, not in water |
别名和识别编码
| Chemical Name | Annamycin is a semi-synthetic doxorubicin analogue annamycin with antineoplastic activity. Annamycin intercalates into DNA and inhibits topoisomerase II, resulting in the inhibition of DNA replication and repair and RNA and protein synthesis. This agent circumvents multidrug-resistance (MDR) transporters, including P-glycoprotein (P-gp). |
|---|---|
| Formula | C26H25IO11 |
| Synonym | Annamycin. |
| IUPAC Name | (7S,9S)-7-(((2R,3R,4R,5R,6S)-4,5-dihydroxy-3-iodo-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7,8,9,10-tetrahydrotetracene-5,12-dione |
| InChIKey | CIDNKDMVSINJCG-GKXONYSUSA-N |
| InChI | InChI=1S/C26H25IO11/c1-9-19(30)24(35)18(27)25(37-9)38-13-7-26(36,14(29)8-28)6-12-15(13)23(34)17-16(22(12)33)20(31)10-4-2-3-5-11(10)21(17)32/h2-5,9,13,18-19,24-25,28,30,33-36H,6-8H2,1H3/t9-,13-,18+,19-,24-,25-,26-/m0/s1 |
| Canonical SMILES | O=C1C2=C(O)C([C@@H](O[C@H]3[C@H](I)[C@H](O)[C@@H](O)[C@H](C)O3)C[C@@](C(CO)=O)(O)C4)=C4C(O)=C2C(C5=C1C=CC=C5)=O |
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- Annamycin is a semi-synthetic doxorubicin analogue annamycin with antineoplastic activity. Annamycin intercalates into DNA and inhibits topoisomerase II, resulting in the inhibition of DNA replication and repair and RNA and protein synthesis. This agent circumvents multidrug-resistance (MDR) transporters, including P-glycoprotein (P-gp).
