Molecule Details
InChIKeyBCGWQEUPMDMJNV-UHFFFAOYSA-N
Compound NameImipramine
Canonical SMILESCN(C)CCCN1c2ccccc2CCc2ccccc21
Clinical Status Clinical Multi-Target
Targets (Human+Pathogen)30
Pfam Stratification Cross-Family
Avg pChEMBL8.06
SourceBindingDB;ChEMBL;TTD_MultiTarget
2D Structure
2D structure
Activity Profile
DrugBank Annotations
DrugBank ID DB00458
Drug NameImipramine
CAS Number50-49-7
Groups approved investigational
ATC Codes N06AA02
DescriptionImipramine, 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