Molecule Details
| InChIKey | KTUFNOKKBVMGRW-UHFFFAOYSA-N |
|---|---|
| Compound Name | Imatinib |
| Canonical SMILES | Cc1ccc(NC(=O)c2ccc(CN3CCN(C)CC3)cc2)cc1Nc1nccc(-c2cccnc2)n1 |
| Clinical Status | Clinical Multi-Target |
| Targets (Human+Pathogen) | 38 |
| Pfam Stratification | Cross-Family |
| Avg pChEMBL | 6.95 |
| Source | ChEMBL;BindingDB;TTD_MultiTarget |
2D Structure
Activity Profile
DrugBank Annotations
| DrugBank ID | DB00619 |
|---|---|
| Drug Name | Imatinib |
| CAS Number | 152459-95-5 |
| Groups | approved investigational |
| ATC Codes | L01EA01 |
| Description | Imatinib is a small molecule kinase inhibitor that revolutionized the treatment of cancer, particularly chronic myeloid leukemia, in 2001.[A249305] It was deemed a "miracle drug" due to its clinical success, as oncologist Dr. Brian noted that "complete hematologic responses were observed in 53 of 54... |
Categories: Amides Antineoplastic Agents Antineoplastic and Immunomodulating Agents BCRP/ABCG2 Inhibitors BCRP/ABCG2 Substrates BSEP/ABCB11 Substrates Bcr-Abl Tyrosine Kinase Inhibitors Benzamides and benzamide derivatives Benzene Derivatives Cancer immunotherapy Cardiotoxic antineoplastic agents Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (moderate) Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (weak) Cytochrome P-450 CYP2D6 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 CYP3A5 Inhibitors Cytochrome P-450 CYP3A5 Inhibitors (strength unknown) Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A7 Inhibitors Cytochrome P-450 CYP3A7 Inhibitors (strength unknown) Cytochrome P-450 CYP3A7 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Drugs causing inadvertant photosensitivity Enzyme Inhibitors Highest Risk QTc-Prolonging Agents Immunosuppressive Agents Immunotherapy Kinase Inhibitor Myelosuppressive Agents OATP1B3 substrates OCT1 substrates OCT2 Inhibitors P-glycoprotein inhibitors P-glycoprotein substrates Photosensitizing Agents Piperazines Protein Kinase Inhibitors Pyrimidines QTc Prolonging Agents Tyrosine Kinase Inhibitors UDP Glucuronosyltransferases Inhibitors UGT2B17 Inhibitors
Cross-references: BindingDB: 31341 ChEBI: 45783 CHEMBL941 ChemSpider: 5101 Drugs Product Database (DPD): 12429 D01441 PDB: STI PharmGKB: PA10804 PubChem:5291 PubChem:46505055 RxCUI: 282388 Therapeutic Targets Database: DNC001383 Wikipedia: Imatinib ZINC: ZINC000019632618
Target Activities (38)
| Target | Gene | Organism | Category | Pfam | pChEMBL | Type | Source |
|---|---|---|---|---|---|---|---|
| P04626 | ERBB2 | Homo sapiens | Human | PF00757 PF14843 PF07714 PF01030 PF21314 | 10.2 | IC50 | ChEMBL |
| P00533 | EGFR | Homo sapiens | Human | PF00757 PF14843 PF07714 PF01030 PF21314 | 10.0 | IC50 | ChEMBL |
| P42684 | ABL2 | Homo sapiens | Human | PF08919 PF07714 PF00017 PF00018 | 7.9 | Kd | ChEMBL;BindingDB |
| P07333 | CSF1R | Homo sapiens | Human | PF00047 PF25305 PF07714 | 7.7 | Kd | ChEMBL;BindingDB |
| Q08345 | DDR1 | Homo sapiens | Human | PF21114 PF00754 PF07714 | 7.7 | Kd | ChEMBL;BindingDB |
| P00918 | CA2 | Homo sapiens | Human | PF00194 | 7.5 | Ki | ChEMBL;BindingDB |
| P18505 | GABRB1 | Homo sapiens | Human | PF02931 PF02932 | 7.5 | pIC50 | TTD_MultiTarget |
| P00915 | CA1 | Homo sapiens | Human | PF00194 | 7.5 | Ki | ChEMBL;BindingDB |
| P16083 | NQO2 | Homo sapiens | Human | PF02525 | 7.4 | IC50 | ChEMBL;BindingDB |
| P09619 | PDGFRB | Homo sapiens | Human | PF00047 PF13927 PF25305 PF07714 | 7.3 | IC50 | ChEMBL;BindingDB |
| P16234 | PDGFRA | Homo sapiens | Human | PF07679 PF25305 PF07714 | 7.3 | IC50 | ChEMBL;BindingDB |
| Q96FL8 | SLC47A1 | Homo sapiens | Human | PF01554 | 7.3 | IC50 | ChEMBL;BindingDB |
| P06239 | LCK | Homo sapiens | Human | PF07714 PF00017 PF00018 | 7.2 | Kd | ChEMBL;BindingDB |
| P10721 | KIT | Homo sapiens | Human | PF00047 PF07714 | 7.2 | IC50 | ChEMBL;BindingDB |
| Q16790 | CA9 | Homo sapiens | Human | PF00194 | 7.1 | Ki | ChEMBL;BindingDB |
| P00519 | ABL1 | Homo sapiens | Human | PF08919 PF07714 PF00017 PF00018 | 7.0 | IC50 | ChEMBL;BindingDB |
| P43166 | CA7 | Homo sapiens | Human | PF00194 | 7.0 | Ki | ChEMBL;BindingDB |
| P36888 | FLT3 | Homo sapiens | Human | PF00047 PF07714 | 6.9 | IC50 | ChEMBL;BindingDB |
| Q16832 | DDR2 | Homo sapiens | Human | PF21114 PF00754 PF07714 | 6.8 | Kd | ChEMBL;BindingDB |
| P11274 | BCR | Homo sapiens | Human | PF09036 PF00168 PF19057 PF00620 PF00621 | 6.8 | IC50 | ChEMBL |
| P24557 | TBXAS1 | Homo sapiens | Human | PF00067 | 6.7 | IC50 | ChEMBL |
| P42685 | FRK | Homo sapiens | Human | PF07714 PF00017 PF00018 | 6.5 | Ki | ChEMBL |
| Q86VL8 | SLC47A2 | Homo sapiens | Human | PF01554 | 6.5 | IC50 | ChEMBL;BindingDB |
| Q8TBX8 | PIP4K2C | Homo sapiens | Human | PF01504 | 6.4 | Kd | ChEMBL;BindingDB |
| P23280 | CA6 | Homo sapiens | Human | PF00194 | 6.4 | Ki | ChEMBL;BindingDB |
| O00571 | DDX3X | Homo sapiens | Human | PF00270 PF00271 | 6.4 | Kd | ChEMBL |
| P07948 | LYN | Homo sapiens | Human | PF07714 PF00017 PF00018 | 6.4 | Kd | ChEMBL;BindingDB |
| Q9ULX7 | CA14 | Homo sapiens | Human | PF00194 | 6.3 | Ki | ChEMBL;BindingDB |
| P07451 | CA3 | Homo sapiens | Human | PF00194 | 6.3 | Ki | ChEMBL;BindingDB |
| P51451 | BLK | Homo sapiens | Human | PF07714 PF00017 PF00018 | 6.3 | Kd | ChEMBL;BindingDB |
| P28223 | HTR2A | Homo sapiens | Human | PF00001 | 6.3 | Ki | ChEMBL |
| P08183 | ABCB1 | Homo sapiens | Human | PF00664 PF00005 | 6.2 | IC50 | ChEMBL;BindingDB |
| Q9UNQ0 | ABCG2 | Homo sapiens | Human | PF01061 PF19055 PF00005 | 6.2 | IC50 | ChEMBL;BindingDB |
| P31645 | SLC6A4 | Homo sapiens | Human | PF03491 PF00209 | 6.1 | Ki | ChEMBL |
| Q8NE63 | HIPK4 | Homo sapiens | Human | PF00069 | 6.0 | Kd | ChEMBL;BindingDB |
| O43570 | CA12 | Homo sapiens | Human | PF00194 | 6.0 | Ki | ChEMBL;BindingDB |
| O14976 | GAK | Homo sapiens | Human | PF00069 PF10409 | 6.0 | Kd | ChEMBL;BindingDB |
| P53779 | MAPK10 | Homo sapiens | Human | PF00069 | 6.0 | Ki | ChEMBL |
DrugBank Target Actions (40)
| Target | Gene | Target Name | Action | Type |
|---|---|---|---|---|
| P02763 | P02763 | Alpha-1-acid glycoprotein 1 | binder | carriers |
| P02768 | ALB | Albumin | binder | carriers |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | inhibitor | enzymes |
| P10635 | CYP2D6 | Cytochrome P450 2D6 | inhibitor | enzymes |
| P11712 | CYP2C9 | Cytochrome P450 2C9 | inhibitor | enzymes |
| P20815 | CYP3A5 | Cytochrome P450 3A5 | inhibitor | enzymes |
| P24462 | CYP3A7 | Cytochrome P450 3A7 | inhibitor | enzymes |
| P05177 | CYP1A2 | Cytochrome P450 1A2 | substrate | enzymes |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | substrate | enzymes |
| P10632 | CYP2C8 | Cytochrome P450 2C8 | substrate | enzymes |
| P10635 | CYP2D6 | Cytochrome P450 2D6 | substrate | enzymes |
| P11712 | CYP2C9 | Cytochrome P450 2C9 | substrate | enzymes |
| P20815 | CYP3A5 | Cytochrome P450 3A5 | substrate | enzymes |
| P24462 | CYP3A7 | Cytochrome P450 3A7 | substrate | enzymes |
| P33261 | CYP2C19 | Cytochrome P450 2C19 | substrate | enzymes |
| P07333 | CSF1R | Macrophage colony-stimulating factor 1 receptor | antagonist | targets |
| P09619 | PDGFRB | Platelet-derived growth factor receptor beta | antagonist | targets |
| P10721 | KIT | Mast/stem cell growth factor receptor Kit | antagonist | targets |
| P16234 | PDGFRA | Platelet-derived growth factor receptor alpha | antagonist | targets |
| Q08345 | DDR1 | Epithelial discoidin domain-containing receptor 1 | antagonist | targets |
| Q16832 | DDR2 | Discoidin domain-containing receptor 2 | antagonist | targets |
| P00519 | ABL1 | Tyrosine-protein kinase ABL1 | inhibitor | targets |
| P07949 | RET | Proto-oncogene tyrosine-protein kinase receptor Ret | inhibitor | targets |
| P11274 | BCR | Breakpoint cluster region protein | inhibitor | targets |
| Q07820 | MCL1 | Induced myeloid leukemia cell differentiation protein Mcl-1 | other/unknown | targets |
| O15244 | SLC22A2 | Solute carrier family 22 member 2 | inhibitor | transporters |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | inhibitor | transporters |
| P33527 | ABCC1 | Multidrug resistance-associated protein 1 | inhibitor | transporters |
| Q9UNQ0 | ABCG2 | Broad substrate specificity ATP-binding cassette transporter ABCG2 | inhibitor | transporters |
| O15245 | SLC22A1 | Solute carrier family 22 member 1 | substrate | transporters |
| O15439 | O15439 | ATP-binding cassette sub-family C member 4 | substrate | transporters |
| O76082 | O76082 | Organic cation/carnitine transporter 2 | substrate | transporters |
| O95342 | ABCB11 | Bile salt export pump | substrate | transporters |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | substrate | transporters |
| P33527 | ABCC1 | Multidrug resistance-associated protein 1 | substrate | transporters |
| P46721 | P46721 | Solute carrier organic anion transporter family member 1A2 | substrate | transporters |
| Q92887 | ABCC2 | ATP-binding cassette sub-family C member 2 | substrate | transporters |
| Q99758 | Q99758 | Phospholipid-transporting ATPase ABCA3 | substrate | transporters |
| Q9NPD5 | SLCO1B3 | Solute carrier organic anion transporter family member 1B3 | substrate | transporters |
| Q9UNQ0 | ABCG2 | Broad substrate specificity ATP-binding cassette transporter ABCG2 | substrate | transporters |