Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0024)
Drug Name
SN-38
Synonyms
Captothecin, 7-ethyl-10-hydroxy-; SN 38 lactone; (+)-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; 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; CHEBI:8988; NSC673596; SN 38; SN38; UNII-0H43101T0J
Indication Colorectal cancer [ICD11: 2B91] Phase 2 [1]
Structure
3D MOL 2D MOL
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
Cross-matching ID
PubChem CID
104842
PubChem SID
13355 ; 515301 ; 622834 ; 10233636 ; 11430409 ; 12012598 ; 14805294 ; 14805295 ; 44434437 ; 49835447 ; 50028359 ; 50112971 ; 56311337 ; 56311445 ; 56311571 ; 56312630 ; 57337873 ; 71831605 ; 80486942 ; 87559919 ; 89360249 ; 92712502 ; 103220117 ; 103996165 ; 104373061 ; 126588659 ; 126625532 ; 126656661 ; 126666539 ; 127855413 ; 134340412 ; 134340540 ; 135062353 ; 135693781 ; 135710073 ; 136377612 ; 136897516 ; 136911131 ; 137138435 ; 142309355 ; 144115510 ; 152059852 ; 152164367 ; 152200177 ; 152245349 ; 162178284 ; 162223790 ; 163367112 ; 164178264 ; 164194982
ChEBI ID
CHEBI:8988
CAS Number
86639-52-3
TTD Drug ID
D0B6YB
Formula
C22H20N2O5
Canonical SMILES
CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)O
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
SN-38G DM006886 N. A. Conjugation - Glucuronidation 1 [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007484 SN-38 SN-38G Conjugation - Glucuronidation UGT1A1 ... [4], [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
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 Effects of green tea compounds on irinotecan metabolism. Drug Metab Dispos. 2007 Feb;35(2):228-33.
3 Correlation between plasma concentration ratios of SN-38 glucuronide and SN-38 and neutropenia induction in patients with colorectal cancer and wild-type UGT1A1 gene. Oncol Lett. 2012 Mar;3(3):694-698.
4 Clinical pharmacokinetics and metabolism of irinotecan (CPT-11)
5 Individualization of Irinotecan Treatment: A Review of Pharmacokinetics, Pharmacodynamics, and Pharmacogenetics

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