Molecule Details
InChIKeyODQWQRRAPPTVAG-UHFFFAOYSA-N
Compound NameDoxepin
Canonical SMILESCN(C)CCC=C1c2ccccc2COc2ccccc21
Clinical Status Clinical Multi-Target
Targets (Human+Pathogen)20
Pfam Stratification Cross-Family
Avg pChEMBL7.24
SourceChEMBL;TTD_MultiTarget
2D Structure
2D structure
Activity Profile
DrugBank Annotations
DrugBank ID DB01142
Drug NameDoxepin
CAS Number1668-19-5
Groups approved
ATC Codes N06AA12 D04AX01
DescriptionDoxepin 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