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
1. Chrencik JE, Staker BL, Burgin AB, Pourquier P, Pommier Y, Stewart L, Redinbo MR. (2004)
Mechanisms of camptothecin resistance by human topoisomerase I mutations.
J Mol Biol, 339 (4): 773-84. [PMID:15165849]
2. Dodds HM, Haaz MC, Riou JF, Robert J, Rivory LP. (1998)
Identification of a new metabolite of CPT-11 (irinotecan): pharmacological properties and activation to SN-38.
J Pharmacol Exp Ther, 286 (1): 578-83. [PMID:9655905]
3. Kunimoto T, Nitta K, Tanaka T, Uehara N, Baba H, Takeuchi M, Yokokura T, Sawada S, Miyasaka T, Mutai M. (1987)
Antitumor activity of 7-ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxy-camptothec in, a novel water-soluble derivative of camptothecin, against murine tumors.
Cancer Res, 47 (22): 5944-7. [PMID:3664496]
4. Matsuzaki T, Yokokura T, Mutai M, Tsuruo T. (1988)
Inhibition of spontaneous and experimental metastasis by a new derivative of camptothecin, CPT-11, in mice.
Cancer Chemother Pharmacol, 21 (4): 308-12. [PMID:3370738]
5. Pommier Y, Redon C, Rao VA, Seiler JA, Sordet O, Takemura H, Antony S, Meng L, Liao Z, Kohlhagen G et al.. (2003)
Repair of and checkpoint response to topoisomerase I-mediated DNA damage.
Mutat Res, 532 (1-2): 173-203. [PMID:14643436]
6. Staker BL, Hjerrild K, Feese MD, Behnke CA, Burgin Jr AB, Stewart L. (2002)
The mechanism of topoisomerase I poisoning by a camptothecin analog.
Proc Natl Acad Sci USA, 99 (24): 15387-92. [PMID:12426403]
7. Tanizawa A, Fujimori A, Fujimori Y, Pommier Y. (1994)
Comparison of topoisomerase I inhibition, DNA damage, and cytotoxicity of camptothecin derivatives presently in clinical trials.
J Natl Cancer Inst, 86 (11): 836-42. [PMID:8182764]
8. Tsuruo T, Matsuzaki T, Matsushita M, Saito H, Yokokura T. (1988)
Antitumor effect of CPT-11, a new derivative of camptothecin, against pleiotropic drug-resistant tumors in vitro and in vivo.
Cancer Chemother Pharmacol, 21 (1): 71-4. [PMID:3342468]