Molecule Details
| InChIKey | UWKQSNNFCGGAFS-XIFFEERXSA-N |
|---|---|
| Compound Name | Irinotecan |
| Canonical SMILES | CCc1c2c(nc3ccc(OC(=O)N4CCC(N5CCCCC5)CC4)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC |
| Clinical Status | Data-mined Candidate |
| Targets (Human+Pathogen) | 4 |
| Pfam Stratification | Cross-Family |
| Avg pChEMBL | 6.62 |
| Source | BindingDB;ChEMBL |
2D Structure
Activity Profile
DrugBank Annotations
| DrugBank ID | DB00762 |
|---|---|
| Drug Name | Irinotecan |
| CAS Number | 97682-44-5 |
| Groups | approved investigational |
| ATC Codes | L01CE02 |
| Description | Irinotecan is a topoisomerase inhibitor used for chemotherapy. It is a water-soluble analogue of [camptothecin], which is extracted from the Chinese tree _Camptotheca acuminate_.[A263376] The bis-piperidine side chain in the structure of irinotecan bestows enhanced water solubility.[A263381] As an a... |
Categories: Alkaloids Antineoplastic Agents Antineoplastic and Immunomodulating Agents BCRP/ABCG2 Substrates Cytochrome P-450 CYP2B6 Substrates Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A5 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A7 Substrates Cytochrome P-450 CYP3A7 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Cytotoxins Enzyme Inhibitors Immunosuppressive Agents Myelosuppressive Agents Narrow Therapeutic Index Drugs OATP1B1/SLCO1B1 Inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Pharmaceutical Preparations Topoisomerase 1 (TOP1) inhibitors Topoisomerase I Inhibitors Topoisomerase Inhibitors UGT1A1 Substrates UGT1A1 Substrates with a Narrow Therapeutic Index UGT1A9 Substrates UGT1A9 Substrates with a Narrow Therapeutic Index
Cross-references: BindingDB: 51762 ChEBI: 80630 CHEMBL481 ChemSpider: 54825 Drugs Product Database (DPD): 11461 C16641 D08086 PDB: CP0 PharmGKB: PA450085 PubChem:60838 PubChem:46505871 RxCUI: 51499 Therapeutic Targets Database: DAP001339 Wikipedia: Irinotecan ZINC: ZINC000001612996
Target Activities (4)
| Target | Gene | Organism | Category | Pfam | pChEMBL | Type | Source |
|---|---|---|---|---|---|---|---|
| P22303 | ACHE | Homo sapiens | Human | PF08674 PF00135 | 7.3 | Ki | ChEMBL;BindingDB |
| P08173 | CHRM4 | Homo sapiens | Human | PF00001 | 6.7 | Ki | ChEMBL |
| P18825 | ADRA2C | Homo sapiens | Human | PF00001 | 6.3 | Ki | ChEMBL |
| P9WH10 | rmlC | Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh) | Pathogen | PF00908 | 6.2 | IC50 | BindingDB |
DrugBank Target Actions (17)
| Target | Gene | Target Name | Action | Type |
|---|---|---|---|---|
| P02768 | ALB | Albumin | binder | carriers |
| P02768 | ALB | Albumin | substrate | carriers |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | inhibitor | enzymes |
| O00748 | CES2 | Human Carboxylesterases | substrate | enzymes |
| O60656 | O60656 | UDP-glucuronosyltransferase 1A9 | substrate | enzymes |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | substrate | enzymes |
| P20815 | CYP3A5 | Cytochrome P450 3A5 | substrate | enzymes |
| P22309 | UGT1A1 | UDP-glucuronosyltransferase 1A1 | substrate | enzymes |
| P24462 | CYP3A7 | Cytochrome P450 3A7 | substrate | enzymes |
| P11387 | TOP1 | DNA topoisomerase 1 | inhibitor | targets |
| Q969P6 | Q969P6 | DNA topoisomerase I, mitochondrial | inhibitor | targets |
| O75751 | SLC22A3 | Solute carrier family 22 member 3 | inhibitor | transporters |
| Q9Y6L6 | SLCO1B1 | Solute carrier organic anion transporter family member 1B1 | inhibitor | transporters |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | substrate | transporters |
| P33527 | ABCC1 | Multidrug resistance-associated protein 1 | substrate | transporters |
| Q92887 | ABCC2 | ATP-binding cassette sub-family C member 2 | substrate | transporters |
| Q9UNQ0 | ABCG2 | Broad substrate specificity ATP-binding cassette transporter ABCG2 | substrate | transporters |