| Identification | Back Directory | [Name]
4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione | [CAS]
130144-34-2 | [Synonyms]
7-Ethyl-10-hydroxycamptothecin
(rac)-7-Ethyl-10-Hydroxy camptothecin
rac-4,11-Diethyl-9-hydroxycamptothecin
(110714-48-2) 7-ethyl-10-hydroxycamptothecin
4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
1H-Pyrano[3,4:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4,11-diethyl-4,9-dihydroxy- | [Molecular Formula]
C22H20N2O5 | [MOL File]
130144-34-2.mol | [Molecular Weight]
392.4 |
| Chemical Properties | Back Directory | [Boiling point ]
810.3±65.0 °C(Predicted) | [density ]
1.51 | [pka]
9.13±0.40(Predicted) | [InChI]
InChI=1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3 | [InChIKey]
FJHBVJOVLFPMQE-UHFFFAOYSA-N | [SMILES]
N1C2C(=CC(O)=CC=2)C(CC)=C2CN3C(C=12)=CC1C(CC)(O)C(=O)OCC=1C3=O |
| Hazard Information | Back Directory | [Description]
7-Ethyl-10-hydroxycamptothecin: a potent topoisomerase I inhibitor
7-Ethyl-10-hydroxycamptothecin (SN-38), as a highly active topoisomerase (Topo) I inhibitor, is the active metabolic product of its prodrug irinotecan (CPT-11) commercially available as Camptosar. By combining with the Topo I-DNA covalent conjugate, the camptothecin analogue forms a ternary complex that blocks the repolymerization of the DNA strands during their replication, eventually leading to the cell apoptosis. Although SN-38 is about 100- to 1000-fold more potent than irinotecan, its clinical application is limited by its poor solubility and nonspecific toxicity[1]. | [Definition]
ChEBI: LSM-6189 is a pyranoindolizinoquinoline. | [References]
[1] Shuangxi Liu. “Co-Prodrugs of 7-Ethyl-10-hydroxycamptothecin and Vorinostat with in Vitro Hydrolysis and Anticancer Effects.” ACS Omega 5 1 (2019): 350–357.
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