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SN-38
Chemical compound / From Wikipedia, the free encyclopedia
SN-38 is an antineoplastic drug. It is the active metabolite of irinotecan (an analog of camptothecin - a topoisomerase 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]
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Names | |
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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) |
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ChEBI | |
ChEMBL | |
ChemSpider |
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ECHA InfoCard | 100.171.154 ![]() |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C22H20N2O5 | |
Molar mass | 392.411 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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SN38 is formed via hydrolysis of irinotecan by carboxylesterases and metabolized via glucuronidation by UGT1A1.
The variant of UGT1A1 in ~10% of Caucasians which leads to poor metabolism of SN-38 predicts irinotecan toxicity, 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 of diarrhoea and myelosuppression experienced by ~25% of the patients administered irinotecan.