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SN-38
Другие языки:

SN-38

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SN-38
SN-38.svg
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
PubChem CID
UNII
  • 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/t22-/m0/s1 checkY
    Key: FJHBVJOVLFPMQE-QFIPXVFZSA-N checkY
  • O=C\1N4\C(=C/C2=C/1COC(=O)[C@]2(O)CC)c3nc5c(c(c3C4)CC)cc(O)cc5
Properties
C22H20N2O5
Molar mass 392.404 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.

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.

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.

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles.

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IrinotecanPathway_WP46359go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article
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IrinotecanPathway_WP46359go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article
|alt=Irinotecan Pathway edit]]
Irinotecan Pathway edit

See also

  • NK012, a nanodevice formulation of SN-38
  • Sacituzumab govitecan, an antibody-drug conjugate that uses SN-38 as the cytotoxic drug.



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