PharmGKB: The Pharmacogenomics Knowledge Base

Drug/Small Molecule:
doxepin

2D structure

Overview

Generic Names: Doxepin Hcl; Doxepin, Hydrochloride; Doxepina [INN-Spanish]; Doxepine; Doxepinum [INN-Latin]
Trade Names: Adapin; Aponal; Curatin; Quitaxon; Triadapin; Zonalon
PharmGKB Accession Id: PA449409

Description

A dibenzoxepin tricyclic compound. It displays a range of pharmacological actions including maintaining adrenergic innervation. Its mechanism of action is not fully understood, but it appears to block reuptake of monoaminergic neurotransmitters into presynaptic terminals. It also possesses anticholinergic activity and modulates antagonism of histamine H(1)- and H(2)-receptors. PubChem (source: Drug Bank)

Indication

For the treatment of psychoneurotic patients with depression and/or anxiety (source: Drug Bank)

ATC Therapeutic Category

  • N06AA:Non-selective monoamine reuptake inhibitors

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

The mechanism of action of doxepin is not completely understood. It is thought that Like amitriptyline, doxepin enhances the actions of norepinephrine and serotonin by blocking their reuptake at the neuronal membrane. Doxepin may also act on histamine H<sub>1</sub>-receptors, resulting in sedative effects, and beta-adrenergic receptors. (source: Drug Bank)

Pharmacology

Doxepin, a tricyclic antidepressant of the dibenzoxepin type, is used to treat depression and anxiety and, topically, pruritus associated with eczema. Doxepin has substantial anticholinergic and sedative effects. (source: Drug Bank)

Food Interactions

Avoid St.John's Wort.
Avoid alcohol.
Avoid excessive quantities of coffee or tea (Caffeine).
Take with food to reduce irritation. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic (source: Drug Bank)

Protein Binding

highly protein-bound (source: Drug Bank)

Absorption

well absorbed from the gut (source: Drug Bank)

Toxicity

LD<sub>50</sub>=26 (mg/kg) (in mice, iv); LD<sub>50</sub>=16 (mg/kg) (in rats, iv); Cardiac dysrhythmias, severe hypotension, convulsions, and CNS depression, including coma. Changes in the electrocardiogram, particularly in QRS axis or width, are clinically significant indicators of tricyclic antidepressant toxicity. (source: Drug Bank)

Isomeric SMILES Code:

CN(C)CCC=C1c2ccccc2COc3c1cccc3 (source: Drug Bank)

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP2D6
  •   
  •   
  • PK
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
KCNH2
  •   
  • PD
  •   
  • FA
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
SLC6A4
  • CO
  •   
  •   
  •   
  • GN
Publications

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
HRH1 Uncurated Annotation (source: Drug Bank)
HRH2 Uncurated Annotation (source: Drug Bank)
SLC6A2 Uncurated Annotation (source: Drug Bank)
SLC6A4 Uncurated Annotation (source: Drug Bank)

The following drugs are in curated knowledge about this drug.

  Drug Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Not annotated
tamoxifen
  •   
  •   
  •   
  •   
  •   
Publications

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
altretamine Uncurated Annotation Risk of severe hypotension (source: Drug Bank)
atazanavir Uncurated Annotation Atazanavir increases the effect and toxicity of tricyclics (source: Drug Bank)
carbamazepine Uncurated Annotation The tricyclic increases the effect of carbamazepine (source: Drug Bank)
cimetidine Uncurated Annotation Cimetidine increases the effect of tricyclic agent (source: Drug Bank)
cisapride Uncurated Annotation Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
clonidine Uncurated Annotation The tricyclic decreases the effect of clonidine (source: Drug Bank)
dobutamine Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
donepezil Uncurated Annotation Possible antagonism of action (source: Drug Bank)
dopamine Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
ephedra Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
ephedrine Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
fenoterol Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
fluoxetine Uncurated Annotation Fluoxetine increases the effect and toxicity of tricyclics (source: Drug Bank)
fluvoxamine Uncurated Annotation Fluvoxamine increases the effect and toxicity of tricyclics (source: Drug Bank)
galantamine Uncurated Annotation Possible antagonism of action (source: Drug Bank)
grepafloxacin Uncurated Annotation Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
guanethidine Uncurated Annotation The tricyclics decreases the effect of guanethidine (source: Drug Bank)
isocarboxazid Uncurated Annotation Possibility of severe adverse effects (source: Drug Bank)
isoproterenol Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
mephentermine Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
mesoridazine Uncurated Annotation Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
metaraminol Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
methoxamine Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
moclobemide Uncurated Annotation Possible severe adverse reaction with this combination (source: Drug Bank)
norepinephrine Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
orciprenaline Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
phenelzine Uncurated Annotation Possibility of severe adverse effects (source: Drug Bank)
phenylephrine Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
phenylpropanolamine Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
pirbuterol Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
procaterol Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
pseudoephedrine Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
quinidine Uncurated Annotation Quinidine increases the effect of tricyclic agent (source: Drug Bank)
quinidine Uncurated Annotation Quinidine increases the effect of tricyclic agent (source: Drug Bank)
rasagiline Uncurated Annotation Possibility of severe adverse effects (source: Drug Bank)
rifabutin Uncurated Annotation The rifamycin decreases the effect of tricyclics (source: Drug Bank)
rifampin Uncurated Annotation The rifamycin decreases the effect of tricyclics (source: Drug Bank)
ritonavir Uncurated Annotation Ritonavir increases the effect and toxicity of tricyclics (source: Drug Bank)
rivastigmine Uncurated Annotation Possible antagonism of action (source: Drug Bank)
salbutamol Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
sibutramine Uncurated Annotation Increased risk of CNS adverse effects (source: Drug Bank)
sparfloxacin Uncurated Annotation Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
terbutaline Uncurated Annotation The tricyclic increases the sympathomimetic effect (source: Drug Bank)
terfenadine Uncurated Annotation Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
thioridazine Uncurated Annotation Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
tranylcypromine Uncurated Annotation Possibility of severe adverse effects (source: Drug Bank)

Curated Information

The following diseases are in curated knowledge about this drug.

  Disease Relationship Evidence
Phenotype data available No genotype data Literature annotations available Not annotated
Depression
  • CO
  •   
  •   
  •   
  • GN
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Depression, Postpartum
  • CO
  •   
  •   
  •   
  • GN
Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB01142
ChEBI ID:
4710
KEGG Compound ID:
C06971
PubChem Compound ID:
667477
PubChem Substance ID:
158785
IUPHAR Ligand ID:
1225

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
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