Molecule Details
| InChIKey | BCGWQEUPMDMJNV-UHFFFAOYSA-N |
|---|---|
| Compound Name | Imipramine |
| Canonical SMILES | CN(C)CCCN1c2ccccc2CCc2ccccc21 |
| Clinical Status | Clinical Multi-Target |
| Targets (Human+Pathogen) | 30 |
| Pfam Stratification | Cross-Family |
| Avg pChEMBL | 8.06 |
| Source | BindingDB;ChEMBL;TTD_MultiTarget |
2D Structure
Activity Profile
DrugBank Annotations
| DrugBank ID | DB00458 |
|---|---|
| Drug Name | Imipramine |
| CAS Number | 50-49-7 |
| Groups | approved investigational |
| ATC Codes | N06AA02 |
| Description | Imipramine, the prototypical tricyclic antidepressant (TCA), is a dibenzazepine-derivative TCA. TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, imipramine does not affect mood or ... |
Categories: Adrenergic Agents Adrenergic Antagonists Adrenergic Uptake Inhibitors Adrenergic alpha-1 Receptor Antagonists Adrenergic alpha-Antagonists Agents producing tachycardia Agents that produce hypertension Agents that reduce seizure threshold Anticholinergic Agents Antidepressive Agents Antidepressive Agents Indicated for Depression Antidepressive Agents, Tricyclic Central Nervous System Agents Central Nervous System Depressants Combined Inhibitors of Serotonin/Norepinephrine Reuptake Cytochrome P-450 CYP1A2 Inhibitors Cytochrome P-450 CYP1A2 Inhibitors (moderate) Cytochrome P-450 CYP1A2 Inhibitors (strength unknown) Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP1A2 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2B6 Substrates Cytochrome P-450 CYP2B6 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2C18 Substrates Cytochrome P-450 CYP2C18 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2C19 Inhibitors Cytochrome P-450 CYP2C19 Inhibitors (strong) Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C19 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2C19 inhibitors (strength unknown) Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (moderate) Cytochrome P-450 CYP2D6 Inhibitors (weak) Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP2D6 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2E1 Inhibitors Cytochrome P-450 CYP2E1 Inhibitors (strength unknown) Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 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 Dibenzazepines Drugs that are Mainly Renally Excreted Heterocyclic Compounds, Fused-Ring Histamine Antagonists Histamine H1 Antagonists Hypotensive Agents Membrane Transport Modulators Moderate Risk QTc-Prolonging Agents Muscarinic Antagonists Narrow Therapeutic Index Drugs Nervous System Neurotoxic agents Neurotransmitter Agents Neurotransmitter Uptake Inhibitors Non-Selective Monoamine Reuptake Inhibitors OCT2 Inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Psychoanaleptics Psychotropic Drugs QTc Prolonging Agents Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome Serotonin 5-HT2 Receptor Antagonists Serotonin 5-HT2A Receptor Antagonists Serotonin 5-HT2C Receptor Antagonists Serotonin Agents Serotonin Modulators Serotonin Receptor Antagonists Tertiary amine tricyclic antidepressants Tricyclics and Other Norepinephrine-reuptake Inhibitors
Cross-references: BindingDB: 50010859 ChEBI: 47499 CHEMBL11 ChemSpider: 3568 Drugs Product Database (DPD): 9267 Guide to Pharmacology: 357 IUPHAR: 357 C07049 D08070 PDB: IXX PharmGKB: PA449969 PubChem:3696 PubChem:46507351 RxCUI: 5691 Therapeutic Targets Database: DAP001154 Wikipedia: Imipramine ZINC: ZINC000000020245
Target Activities (30)
| Target | Gene | Organism | Category | Pfam | pChEMBL | Type | Source |
|---|---|---|---|---|---|---|---|
| A5X5Y0 | HTR3E | Homo sapiens | Human | PF02931 PF02932 | 9.0 | IC50 | ChEMBL |
| O95264 | HTR3B | Homo sapiens | Human | PF02931 PF02932 | 9.0 | IC50 | ChEMBL |
| P08908 | HTR1A | Homo sapiens | Human | PF00001 | 9.0 | IC50 | ChEMBL |
| P28221 | HTR1D | Homo sapiens | Human | PF00001 | 9.0 | IC50 | ChEMBL |
| P28222 | HTR1B | Homo sapiens | Human | PF00001 | 9.0 | IC50 | ChEMBL |
| P28566 | HTR1E | Homo sapiens | Human | PF00001 | 9.0 | IC50 | ChEMBL |
| P30939 | HTR1F | Homo sapiens | Human | PF00001 | 9.0 | IC50 | ChEMBL |
| P34969 | HTR7 | Homo sapiens | Human | PF00001 | 9.0 | Ki | ChEMBL;BindingDB |
| P41595 | HTR2B | Homo sapiens | Human | PF00001 | 9.0 | IC50 | ChEMBL |
| P46098 | HTR3A | Homo sapiens | Human | PF02931 PF02932 | 9.0 | IC50 | ChEMBL |
| P47898 | HTR5A | Homo sapiens | Human | PF00001 | 9.0 | IC50 | ChEMBL |
| P50406 | HTR6 | Homo sapiens | Human | PF00001 | 9.0 | Ki | ChEMBL;BindingDB |
| Q13639 | HTR4 | Homo sapiens | Human | PF00001 | 9.0 | IC50 | ChEMBL |
| Q70Z44 | HTR3D | Homo sapiens | Human | PF02931 PF02932 | 9.0 | IC50 | ChEMBL |
| Q8WXA8 | HTR3C | Homo sapiens | Human | PF02931 PF02932 | 9.0 | IC50 | ChEMBL |
| P31645 | SLC6A4 | Homo sapiens | Human | PF03491 PF00209 | 8.4 | Ki | ChEMBL;BindingDB |
| P35367 | HRH1 | Homo sapiens | Human | PF00001 | 7.7 | Ki | ChEMBL;BindingDB |
| P35348 | ADRA1A | Homo sapiens | Human | PF00001 | 7.5 | Ki | BindingDB |
| P11229 | CHRM1 | Homo sapiens | Human | PF00001 | 7.4 | Ki | BindingDB |
| P08172 | CHRM2 | Homo sapiens | Human | PF00001 | 7.3 | Ki | BindingDB |
| P20309 | CHRM3 | Homo sapiens | Human | PF00001 | 7.2 | Ki | BindingDB |
| P23975 | SLC6A2 | Homo sapiens | Human | PF00209 | 7.1 | Ki | ChEMBL;BindingDB |
| P08912 | CHRM5 | Homo sapiens | Human | PF00001 | 7.1 | Ki | BindingDB |
| P28223 | HTR2A | Homo sapiens | Human | PF00001 | 7.0 | Ki | ChEMBL;BindingDB |
| P08173 | CHRM4 | Homo sapiens | Human | PF00001 | 7.0 | Ki | BindingDB |
| P28335 | HTR2C | Homo sapiens | Human | PF00001 | 6.8 | Ki | ChEMBL;BindingDB |
| P35462 | DRD3 | Homo sapiens | Human | PF00001 | 6.4 | Ki | BindingDB |
| O15244 | SLC22A2 | Homo sapiens | Human | PF00083 | 6.2 | IC50 | ChEMBL;BindingDB |
| P14416 | DRD2 | Homo sapiens | Human | PF00001 | 6.2 | Ki | ChEMBL;BindingDB |
| P18505 | GABRB1 | Homo sapiens | Human | PF02931 PF02932 | Clinical | TTD_MultiTarget | TTD_MultiTarget |
DrugBank Target Actions (40)
| Target | Gene | Target Name | Action | Type |
|---|---|---|---|---|
| P02763 | P02763 | Alpha-1-acid glycoprotein 1 | binder | carriers |
| P02768 | ALB | Albumin | binder | carriers |
| P05177 | CYP1A2 | Cytochrome P450 1A2 | inhibitor | enzymes |
| P05181 | CYP2E1 | Cytochrome P450 2E1 | inhibitor | enzymes |
| P10635 | CYP2D6 | Cytochrome P450 2D6 | inhibitor | enzymes |
| P33261 | CYP2C19 | Cytochrome P450 2C19 | inhibitor | enzymes |
| P05177 | CYP1A2 | Cytochrome P450 1A2 | substrate | enzymes |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | substrate | enzymes |
| P10635 | CYP2D6 | Cytochrome P450 2D6 | substrate | enzymes |
| P20813 | CYP2B6 | Cytochrome P450 2B6 | substrate | enzymes |
| P24462 | CYP3A7 | Cytochrome P450 3A7 | substrate | enzymes |
| P33260 | CYP2C18 | Cytochrome P450 2C18 | substrate | enzymes |
| P33261 | CYP2C19 | Cytochrome P450 2C19 | substrate | enzymes |
| P08908 | HTR1A | 5-hydroxytryptamine receptor 1A | activator | targets |
| P08172 | CHRM2 | Muscarinic acetylcholine receptor M2 | antagonist | targets |
| P08173 | CHRM4 | Muscarinic acetylcholine receptor M4 | antagonist | targets |
| P08912 | CHRM5 | Muscarinic acetylcholine receptor M5 | antagonist | targets |
| P11229 | CHRM1 | Muscarinic acetylcholine receptor M1 | antagonist | targets |
| P20309 | CHRM3 | Muscarinic acetylcholine receptor M3 | antagonist | targets |
| P25100 | ADRA1D | Alpha-1D adrenergic receptor | antagonist | targets |
| P28223 | HTR2A | 5-hydroxytryptamine receptor 2A | antagonist | targets |
| P28335 | HTR2C | 5-hydroxytryptamine receptor 2C | antagonist | targets |
| P34969 | HTR7 | 5-hydroxytryptamine receptor 7 | antagonist | targets |
| P35348 | ADRA1A | Alpha-1A adrenergic receptor | antagonist | targets |
| P35367 | HRH1 | Histamine H1 receptor | antagonist | targets |
| P35368 | ADRA1B | Alpha-1B adrenergic receptor | antagonist | targets |
| P14416 | DRD2 | D(2) dopamine receptor | binder | targets |
| P21728 | DRD1 | D(1) dopamine receptor | binder | targets |
| P50406 | HTR6 | 5-hydroxytryptamine receptor 6 | binder | targets |
| O95259 | KCNH1 | Voltage-gated delayed rectifier potassium channel KCNH1 | inhibitor | targets |
| P23975 | SLC6A2 | Sodium-dependent noradrenaline transporter | inhibitor | targets |
| P31645 | SLC6A4 | Sodium-dependent serotonin transporter | inhibitor | targets |
| Q01959 | SLC6A3 | Sodium-dependent dopamine transporter | inhibitor | targets |
| Q12809 | KCNH2 | Voltage-gated inwardly rectifying potassium channel KCNH2 | inhibitor | targets |
| Q9NZV8 | KCND2 | A-type voltage-gated potassium channel KCND2 | inhibitor | targets |
| Q9UK17 | KCND3 | A-type voltage-gated potassium channel KCND3 | inhibitor | targets |
| O15244 | SLC22A2 | Solute carrier family 22 member 2 | inhibitor | transporters |
| O75751 | SLC22A3 | Solute carrier family 22 member 3 | inhibitor | transporters |
| Q9H015 | Q9H015 | Solute carrier family 22 member 4 | inhibitor | transporters |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | substrate | transporters |