irinotecan   Click here for help

GtoPdb Ligand ID: 6823

Synonyms: (+)-irinotecan | biotecan | Campto® | Camptosar® | CPT-11 | irinotecan hydrochloride | Onivyde®
Approved drug PDB Ligand
irinotecan is an approved drug (FDA (1996), EMA (2016))
Compound class: Synthetic organic
Comment: Irinotecan is a semisynthetic analogue of the natural plant alkaloid camptothecin (PubChem CID 24360) which functions as a DNA replication inhibitor by binding to topoisomerase I/DNA complexes [5]. Camptothecin was first isolated from the bark and stem of Camptotheca acuminata, the Chinsese happy tree.
The PubChem CID linked here is the same isomer as recorded in irinotecan's INN record.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: irinotecan

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 114.2
Molecular weight 586.28
XLogP 4.64
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES CCC1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)CC)OC(=O)N1CCC(CC1)N1CCCCC1
Isomeric SMILES CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)CC)OC(=O)N1CCC(CC1)N1CCCCC1
InChI InChI=1S/C33H38N4O6/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3/t33-/m0/s1
Bioactivity Comments
Preclinical studies of irinotecan focussed on its anti-tumour effects [3-4,8], and we have been unable to find affinity data to substantiate its molecular mechanism of action. We map the primary target as DNA topoisomerase I (TOP1) for data metrics purposes, based on irinotecan's similarity to camptothecin and topotecan, which have both been reported in crystal structures with TOP1/DNA complexes (see Protein Data Bank entries 1RRJ [1] and 1K4T [6]).
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
DNA topoisomerase I Primary target of this compound Bt Inhibitor Inhibition - - - 2,7
Description: Effect of irinotecan on topoisomerase I-mediated DNA cleavage