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.
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2D Structure
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Physico-chemical Properties
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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
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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
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Summary of Clinical Use Click here for help
A topoisomerase inhibitor used for the treatment of cancer: colon cancer, especially in combination with other chemotherapy agents.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Irinotecan has the same molecular mechanism of action as its parent molecule camptothecin, i.e. it interferes with DNA replication by binding to DNA topoisomerase I/DNA complexes. This action leads to DNA damage and apoptosis.
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