SN-38

SN-38
Other names 7-Ethyl-10-hydroxy-camptothecin
Identifiers
CAS number	86639-52-3 N
PubChem	104842
ChemSpider	94634 Y
UNII	0H43101T0J Y
ChEMBL	CHEMBL837 Y
Jmol-3D images	Image 1
SMILES O=C\1N4\C(=C/C2=C/1COC(=O)[C@]2(O)CC)c3nc5c(c(c3C4)CC)cc(O)cc5
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/t22-/m0/s1 Y Key: FJHBVJOVLFPMQE-QFIPXVFZSA-N Y InChI=1/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 Key: FJHBVJOVLFPMQE-QFIPXVFZBM
Properties
Molecular formula	C22H20N2O5
Molar mass	392.404 g/mol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

SN-38 is the active metabolite of irinotecan (an analog of camptothecin - a topoisomerase I inhibitor); it is 1000 times more active 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 metabolized via glucoronidation by UGT1A1.

The variant of UGT1A1 in ~10% of Caucasians which leads to poor metabolization of Irinotecan predicts Irinotecan toxicity, as it cannot be excreted from the body in its SN-38 form.

SN-38 is lost into the bile and feces. 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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Irinotecan Pathway edit

See also

• NK012, a nanodevice formulation of SN-38