7-Ethyl-10-hydroxycamptothecin Chemical Properties

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

7-Ethyl-10-hydroxycamptothecin Usage And Synthesis

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.