Drug Information

General Information
Drug ID
DR00161
Drug Name
SN-38
Synonyms
(+)-7-ETHYL-10-HYDROXYCAMPTOTHECIN; (S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; 0H43101T0J; 10-Hydroxy-7-ethylcamptothecin; 113015-38-6; 7-Ethyl-10-hydroxy camptothecin; 7-Ethyl-10-hydroxy-20(S)-camptothecin; 7-Ethyl-10-hydroxy-camptothecin; 7-Ethyl-10-hydroxycamptothecin; 7-Ethyl-10-hydroxycamptothecine; 86639-52-3; Captothecin, 7-ethyl-10-hydroxy-; LE-SN38; NSC673596; SN 38; SN 38 lactone; SN38; UNII-0H43101T0J
Drug Type
Small molecular drug
Indication Colon cancer [ICD11:2B90.Z] Phase 2 [1]
Structure
3D MOL 2D MOL
Formula
C22H20N2O5
Canonical SMILES
CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)O
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
InChIKey
FJHBVJOVLFPMQE-QFIPXVFZSA-N
CAS Number
CAS 86639-52-3
Pharmaceutical Properties Molecular Weight 392.4 Topological Polar Surface Area 100
Heavy Atom Count 29 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
XLogP
1.4
PubChem CID
104842
PubChem SID
10233636 ,103220117 ,103996165 ,104373061 ,11430409 ,12012598 ,126588659 ,126625532 ,126656661 ,126666539 ,127855413 ,13355 ,134340412 ,134340540 ,135062353 ,135693781 ,135710073 ,136377612 ,136897516 ,136911131 ,137138435 ,142309355 ,144115510 ,14805294 ,14805295 ,152059852 ,152164367 ,152200177 ,152245349 ,162178284 ,162223790 ,163367112 ,164178264 ,164194982 ,44434437 ,49835447 ,50028359 ,50112971 ,515301 ,56311337 ,56311445 ,56311571 ,56312630 ,57337873 ,622834 ,71831605 ,80486942 ,87559919 ,89360249 ,92712502
ChEBI ID
CHEBI:8988
TTD Drug ID
D0B6YB
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
MRP1 Transporter Info Multidrug resistance-associated protein 1 Substrate [3]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [4]
MRP4 Transporter Info Multidrug resistance-associated protein 4 Substrate [5]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [6]
OATP1B3 Transporter Info Organic anion transporting polypeptide 1B3 Substrate [7]
Drug-Transporter Activity Data
Drug-Transporter Activity Data BCRP Transporter Info Km =4 microM Human lung carcinoma cells (PC-6/SN2-5H)-BCRP [2]
MRP2 Transporter Info Km =180 microM Bile canalicular membrane vesicles-MRP2 [4]
References
1 Randomized phase 2 study of pegylated SN-38 (EZN-2208) or irinotecan plus cetuximab in patients with advanced colorectal cancer. Cancer. 2013 Dec 15;119(24):4223-30.
2 Transport of 7-ethyl-10-hydroxycamptothecin (SN-38) by breast cancer resistance protein ABCG2 in human lung cancer cells. Biochem Biophys Res Commun. 2001 Nov 9;288(4):827-32.
3 ATP-Dependent efflux of CPT-11 and SN-38 by the multidrug resistance protein (MRP) and its inhibition by PAK-104P. Mol Pharmacol. 1999 May;55(5):921-8.
4 Biliary excretion mechanism of CPT-11 and its metabolites in humans: involvement of primary active transporters. Cancer Res. 1998 Nov 15;58(22):5137-43.
5 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
6 Organic anion transporting polypeptide 1B1: a genetically polymorphic transporter of major importance for hepatic drug uptake. Pharmacol Rev. 2011 Mar;63(1):157-81.
7 Rapid screening of antineoplastic candidates for the human organic anion transporter OATP1B3 substrates using fluorescent probes. Cancer Lett. 2008 Feb 18;260(1-2):163-9.

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