SN-38

{{chembox

| Verifiedfields = changed

| verifiedrevid = 464385520

| ImageFile = SN-38.svg

| ImageSize =

| PIN = (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

| OtherNames = 7-Ethyl-10-hydroxycamptothecin

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 6925

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 94634

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 8988

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 837

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FJHBVJOVLFPMQE-QFIPXVFZSA-N

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 86639-52-3

| PubChem = 104842

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 0H43101T0J

| SMILES = O=C\1N4\C(=C/C2=C/1COC(=O)[C@]2(O)CC)c3nc5c(c(c3C4)CC)cc(O)cc5

}}

|Section2={{Chembox Properties

| C=22|H=20|N=2|O=5

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|Section3={{Chembox Hazards

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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.{{cite web | url = http://labeling.pfizer.com/ShowLabeling.aspx?id=533 | title = CAMPTOSAR- irinotecan hydrochloride injection, solution Pharmacia & Upjohn Company LLC }}

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.{{cite journal |author=O'Dwyer PJ, Catalano RB |title=Uridine diphosphate glucuronosyltransferase (UGT) 1A1 and irinotecan: practical pharmacogenomics arrives in cancer therapy |journal=J. Clin. Oncol. |volume=24 |issue=28 |pages=4534–8 |date=October 2006 |pmid=17008691 |doi=10.1200/JCO.2006.07.3031 |url=http://www.jco.org/cgi/pmidlookup?view=long&pmid=17008691|doi-access=free }}

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.