Molecule Details
| InChIKey | ODQWQRRAPPTVAG-UHFFFAOYSA-N |
|---|---|
| Compound Name | Doxepin |
| Canonical SMILES | CN(C)CCC=C1c2ccccc2COc2ccccc21 |
| Clinical Status | Clinical Multi-Target |
| Targets (Human+Pathogen) | 20 |
| Pfam Stratification | Cross-Family |
| Avg pChEMBL | 7.24 |
| Source | ChEMBL;TTD_MultiTarget |
2D Structure
Activity Profile
DrugBank Annotations
| DrugBank ID | DB01142 |
|---|---|
| Drug Name | Doxepin |
| CAS Number | 1668-19-5 |
| Groups | approved |
| ATC Codes | N06AA12 D04AX01 |
| Description | Doxepin is a psychotropic agent with antidepressant and anxiolytic properties.[T559] It is a tertiary amine that can be presented as (E) and (Z) stereoisomers with the (Z) stereoisomer corresponding to [cidoxepin]. Doxepin commonly produces a 5:1 (E):(Z) racemic mixture.[T83] In a strict sense, doxe... |
Categories: Acid Reducers Adrenergic Antagonists 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 Antipruritics and Local Anesthetics Antipruritics, Incl. Antihistamines, Anesthetics, Etc. Central Nervous System Agents Central Nervous System Depressants Combined Inhibitors of Serotonin/Norepinephrine Reuptake Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Dermatologicals Dibenzoxepins Drugs that are Mainly Renally Excreted Ethers, Cyclic Heterocyclic Compounds, Fused-Ring Histamine Agents Histamine Antagonists Histamine H1 Antagonists Histamine H2 Antagonists Hypnotics and Sedatives Muscarinic Antagonists Nervous System Neurotoxic agents Neurotransmitter Agents Non-Selective Monoamine Reuptake Inhibitors P-glycoprotein substrates Potential QTc-Prolonging Agents Psychoanaleptics Psychotropic Drugs QTc Prolonging Agents Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome Serotonin 5-HT1 Receptor Antagonists Serotonin 5-HT1A Receptor Antagonists Serotonin 5-HT2 Receptor Antagonists Serotonin 5-HT2A Receptor Antagonists Serotonin 5-HT2C Receptor Antagonists Serotonin Agents Serotonin Modulators Serotonin Receptor Antagonists Sleep Aids, Pharmaceutical Tertiary amine tricyclic antidepressants Tricyclics and Other Norepinephrine-reuptake Inhibitors
Cross-references: BindingDB: 50225488 ChEBI: 4710 CHEMBL1628227 ChemSpider: 3046 Drugs Product Database (DPD): 11107 Guide to Pharmacology: 1225 IUPHAR: 1225 C06971 D07875 PharmGKB: PA449409 PubChem:667468 PubChem:46505232 RxCUI: 3638 Therapeutic Targets Database: DAP000177 Wikipedia: Doxepin
Target Activities (20)
| Target | Gene | Organism | Category | Pfam | pChEMBL | Type | Source |
|---|---|---|---|---|---|---|---|
| P35367 | HRH1 | Homo sapiens | Human | PF00001 | 9.7 | Ki | ChEMBL |
| P08173 | CHRM4 | Homo sapiens | Human | PF00001 | 7.8 | IC50 | ChEMBL |
| P28223 | HTR2A | Homo sapiens | Human | PF00001 | 7.7 | IC50 | ChEMBL |
| P08912 | CHRM5 | Homo sapiens | Human | PF00001 | 7.7 | IC50 | ChEMBL |
| P23975 | SLC6A2 | Homo sapiens | Human | PF00209 | 7.5 | IC50 | ChEMBL |
| P31645 | SLC6A4 | Homo sapiens | Human | PF03491 PF00209 | 7.5 | IC50 | ChEMBL |
| P20309 | CHRM3 | Homo sapiens | Human | PF00001 | 7.5 | IC50 | ChEMBL |
| P28335 | HTR2C | Homo sapiens | Human | PF00001 | 7.5 | IC50 | ChEMBL |
| P11229 | CHRM1 | Homo sapiens | Human | PF00001 | 7.4 | IC50 | ChEMBL |
| P18089 | ADRA2B | Homo sapiens | Human | PF00001 | 7.3 | IC50 | ChEMBL |
| P35348 | ADRA1A | Homo sapiens | Human | PF00001 | 7.2 | pIC50 | TTD_MultiTarget |
| P41595 | HTR2B | Homo sapiens | Human | PF00001 | 7.2 | IC50 | ChEMBL |
| P25100 | ADRA1D | Homo sapiens | Human | PF00001 | 7.1 | IC50 | ChEMBL |
| P50406 | HTR6 | Homo sapiens | Human | PF00001 | 6.8 | Ki | ChEMBL |
| P08172 | CHRM2 | Homo sapiens | Human | PF00001 | 6.8 | IC50 | ChEMBL |
| P18825 | ADRA2C | Homo sapiens | Human | PF00001 | 6.8 | Ki | ChEMBL |
| Q99720 | SIGMAR1 | Homo sapiens | Human | PF04622 | 6.4 | IC50 | ChEMBL |
| P35462 | DRD3 | Homo sapiens | Human | PF00001 | 6.3 | Ki | ChEMBL |
| P21728 | DRD1 | Homo sapiens | Human | PF00001 | 6.3 | IC50 | ChEMBL |
| P08913 | ADRA2A | Homo sapiens | Human | PF00001 | 6.3 | Ki | ChEMBL |
DrugBank Target Actions (28)
| Target | Gene | Target Name | Action | Type |
|---|---|---|---|---|
| P02763 | P02763 | Alpha-1-acid glycoprotein 1 | binder | carriers |
| P02768 | ALB | Albumin | binder | carriers |
| P10635 | CYP2D6 | Cytochrome P450 2D6 | inhibitor | enzymes |
| P05177 | CYP1A2 | Cytochrome P450 1A2 | substrate | enzymes |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | substrate | enzymes |
| P10635 | CYP2D6 | Cytochrome P450 2D6 | substrate | enzymes |
| P11712 | CYP2C9 | Cytochrome P450 2C9 | substrate | enzymes |
| P33261 | CYP2C19 | Cytochrome P450 2C19 | substrate | enzymes |
| P08172 | CHRM2 | Muscarinic acetylcholine receptor M2 | antagonist | targets |
| P08173 | CHRM4 | Muscarinic acetylcholine receptor M4 | antagonist | targets |
| P08908 | HTR1A | 5-hydroxytryptamine receptor 1A | 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 |
| P25021 | HRH2 | Histamine H2 receptor | 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 |
| P35348 | ADRA1A | Alpha-1A adrenergic receptor | antagonist | targets |
| P35367 | HRH1 | Histamine H1 receptor | antagonist | targets |
| P35368 | ADRA1B | Alpha-1B adrenergic receptor | antagonist | targets |
| P41595 | HTR2B | 5-hydroxytryptamine receptor 2B | antagonist | targets |
| P50406 | HTR6 | 5-hydroxytryptamine receptor 6 | binder | targets |
| Q9H3N8 | HRH4 | Histamine H4 receptor | binder | targets |
| P23975 | SLC6A2 | Sodium-dependent noradrenaline transporter | inhibitor | targets |
| P31645 | SLC6A4 | Sodium-dependent serotonin transporter | inhibitor | targets |
| Q12809 | KCNH2 | Voltage-gated inwardly rectifying potassium channel KCNH2 | inhibitor | targets |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | substrate | transporters |