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| Names | |
|---|---|
| Preferred IUPAC name (4S)-4,11-Diethyl-4,9-dihydroxy-1,4-dihydro-3H,14H-pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14-dione | |
| Other names 7-Ethyl-10-hydroxycamptothecin | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
|
| ECHA InfoCard | 100.171.154 |
| UNII | |
| |
| |
| Properties | |
| C22H20N2O5 | |
| Molar mass | 392.411 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
SN-38 is anantineoplastic drug. It is theactive metabolite ofirinotecan (an analog ofcamptothecin - atopoisomerase I inhibitor) but has 1000 times more activity than irinotecan itself. In vitro cytotoxicity assays show that the potency of SN-38 relative to irinotecan varies from 2- to 2000-fold.[1]
SN38 is formed via hydrolysis of irinotecan bycarboxylesterases and metabolized viaglucuronidation byUGT1A1.
The variant of UGT1A1 in ~10% of Caucasians which leads to poor metabolism of SN-38 predicts irinotecantoxicity, as it is then less easily excreted from the body in its SN-38 glucuronide form.[2]
SN-38 and its glucuronide are lost into the bile and intestines. It can cause the symptoms ofdiarrhoea andmyelosuppression experienced by ~25% of the patients administeredirinotecan.
Click on genes, proteins and metabolites below to link to respective articles.[§ 1]
