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Doxepin is a tricyclic antidepressant (TCA) used to treat major depressive disorder, anxiety disorders, and chronic hives, and for short-term help with trouble remaining asleep after going to bed (a form of insomnia ).
At doses used to treat depression, doxepin appears to inhibit the reuptake of serotonin and norepinephrine and to have antihistamine, adrenergic and serotonin receptor antagonistic, and anticholinergic activities; at low doses used to treat insomnia it appears to be selective for the histamine H 1 receptor.
It was introduced under the brand names Quitaxon and Aponal by Boehringer, which discovered it, and as Sinequan by Pfizer,
1 Medical uses
2 Contraindications
2.1 Pregnancy and lactation
3 Side effects
4 Overdose
5 Interactions
6 Pharmacology
6.1 Pharmacodynamics
6.1.1 As a hypnotic
6.1.2 CYP2D6 inhibition
6.2 Pharmacokinetics
6.2.1 Absorption
6.2.2 Distribution
6.2.3 Metabolism
6.2.4 Elimination
6.3 Pharmacogenetics
7 Chemistry
8 History
9 Society and culture
9.1 Generic names
9.2 Brand names
9.3 Approvals
10 Research
10.1 Antihistamine
10.2 Headache
11 References
Medical uses
Doxepin is used as a pill to treat major depressive disorder, anxiety disorders, and chronic hives, and for short-term help with trouble remaining asleep after going to bed (a form of insomnia ).
In 2016 the American College of Physicians advised that insomnia be treated first by treating comorbid conditions, then with cognitive behavioral therapy and behavioral changes, and then with drugs; doxepin was among those recommended for short-term help maintaining sleep, on the basis of weak evidence.
A 2010 review found that topical doxepin is useful to treat itchiness.
A 2010 review of treatments for chronic hives found that doxepin had been superseded by better drugs but was still sometimes useful as a second-line treatment.
Known contraindications include:
Hypersensitivities to doxepin, other TCAs, or any of the excipients inside the product used
A predisposition to developing urinary retention such as in benign prostatic hyperplasia
Use of monoamine oxidase inhibitors in last 14 days
Pregnancy and lactation
Its use in pregnant and lactating women is advised against, although the available preclinical evidence (based on animal studies) suggests it is unlikely to cause any deleterious effects on fetal development.
Side effects
See also: List of side effects of doxepin
Doxepin is licensed to be used in much smaller doses (viz., 3 mg and 6 mg) in some countries the side effects’ profile of which may differ from this list.
Central nervous system: fatigue, dizziness, drowsiness, lightheadedness, confusion, nightmares, agitation, increased anxiety, difficulty sleeping, seizures (infrequently), temporary confusion (delirium), rarely induction of hypomania and schizophrenia (stop medication immediately), extrapyramidal side effects (rarely), abuse in patients with polytoxicomania (rarely), ringing in the ears (tinnitus)
Anticholinergic: dry mouth, constipation, even ileus (rarely), difficulties in urinating, sweating, precipitation of glaucoma
Antiadrenergic: Low blood pressure, (if patient arises too fast from the lying/sitting position to standing—known as orthostatic hypotension ), abnormal heart rhythms (e.g., sinus tachycardia, bradycardia, and atrioventricular block )
Allergic/toxic: skin rash, photosensitivity, liver damage of the cholestatic type (rarely), hepatitis (extremely rare), leuko – or thrombocytopenia (rarely), agranulocytosis (very rarely), hypoplastic anemia (rarely)
Others: frequently increased appetite, weight gain, rarely nausea, frequently impaired sexual function in men ( impotence, ejaculation -difficulties), rarely high blood pressure, rarely nerve damage to multiple nerves, in both sexes breast-enlargement and secretion of milk from breast tissue (rarely)
May increase or decrease liver function in some patients.
Main article: Tricyclic antidepressant overdose
Like other TCAs, doxepin is highly toxic in cases of overdose.
Doxepin should not be used within 14 days of using a monoamine oxidase inhibitor (MAOI) such as phenelzine due to the potential for hypertensive crisis or serotonin syndrome to develop.
See also: Pharmacology of antidepressants and Tricyclic antidepressant § Binding profiles
K i (nM)
68–95 210 ( IC 50 )
30–58 13 ( IC 50 )
>10,000 4,600 ( IC 50 )
5-HT 1A
5-HT 2A
5-HT 2B
5-HT 2C
200 8.8
Human Rat
5-HT 3
5-HT 6
5-HT 7
α 1
   α 1B
α 2A
α 2B
α 2C
D 2
H 1
H 2
H 3
H 4
   M 1
   M 2
   M 3
   M 4
   M 5
6,500 ( IC 50 )
Values are K i, unless otherwise specified. The smaller the value, the more strongly the drug binds to the site.
Doxepin is a reuptake inhibitor of serotonin and norepinephrine, or a serotonin–norepinephrine reuptake inhibitor (SNRI), and has additional antiadrenergic, antihistamine, antiserotonergic, and anticholinergic activities.
Extremely strong: H 1 receptor
Strong: 5-HT 2, α 1 -adrenergic, and muscarinic acetylcholine receptors
Moderate: 5-HT 1 receptors
Weak: α 2 -adrenergic and D 2 receptors
Based on its IC 50 values for monoamine reuptake inhibition, doxepin is relatively selective for inhibition of norepinephrine reuptake with much weaker effects on serotonin reuptake and negligible influence on dopamine reuptake.
The major metabolite of doxepin, nordoxepin (desmethyldoxepin), is pharmacologically active similarly,
Antidepressant doses of doxepin are defined as 25 to 300 mg/day, although are typically above 75 mg/day.
Doxepin is a mixture of ( E ) and ( Z ) stereoisomers with an approximate ratio of 85:15.
As a hypnotic
TCAs and TeCAs at H 1 and mACh receptors
H 1
Values are K i (nM).
Doxepin is a highly potent antihistamine, with this being its strongest activity.
The H 1 receptor antagonism of doxepin is responsible for its hypnotic effects and its effectiveness in the treatment of insomnia at low doses.
The effect sizes of very low-dose doxepin in the treatment of insomnia range from small to medium.
At very low doses, doxepin has not shown discontinuation or withdrawal effects nor rebound insomnia.
Antagonism of the H 1, 5-HT 2A, 5-HT 2C, and α 1 -adrenergic receptors is thought to have sleep-promoting effects and to be responsible for the sedative effects of TCAs including those of doxepin.
Doxepin at a dose of 25 mg/day for 3 weeks has been found to decrease cortisol levels by 16% in adults with chronic insomnia and to increase melatonin production by 26% in healthy volunteers.
CYP2D6 inhibition
Doxepin has been identified as an inhibitor of CYP2D6 in vivo in a study of human patients being treated with 75 to 250 mg/day for depression.
Pharmacokinetics of doxepin (25 mg)
T max (hours)
Mean: 2.9 Range: 2–4
Mean: ND Range: 2–10
C max (ng/mL)
Mean: ND Range: 8.8–45.8
Mean: 9.7 Range: 4.8–14.5
V D (L/kg)
Protein binding
t 1/2 (hours)
Mean: 17 Range: 8–24
Mean: 31 Range: ND
Metabolic enzymes
Major: CYP2D6, CYP2C19 Minor: CYP1A2, CYP2C9, CYP3A4
Metabolic pathways
N- Demethylation, N- oxidation, hydroxylation, glucuronidation
Doxepin is well- absorbed from the gastrointestinal tract but between 55 and 87% undergoes first-pass metabolism in the liver,
Doxepin is widely distributed throughout the body and is approximately 80% plasma protein-bound, specifically to albumin and α 1 -acid glycoprotein.
Doxepin is extensively metabolized by the liver via oxidation and N – demethylation.
Nordoxepin is a mixture of ( E ) and ( Z ) stereoisomers similarly to doxepin.
Doxepin is eliminated primarily in the urine and predominantly in the form of glucuronide conjugates, with less than 3% of a dose excreted unchanged as doxepin or nordoxepin.
Since doxepin is mainly metabolized by CYP2D6, CYP2C9, and CYP2C19, genetic variations within the genes coding for these enzymes can affect its metabolism, leading to changes in the concentrations of the drug in the body. Increased concentrations of doxepin may increase the risk for side effects, including anticholinergic and nervous system adverse effects, while decreased concentrations may reduce the drug’s efficacy.
Individuals can be categorized into different types of cytochrome P450 metabolizers depending on which genetic variations they carry. These metabolizer types include poor, intermediate, extensive, and ultrarapid metabolizers. Most people are extensive metabolizers, and have “normal” metabolism of doxepin. Poor and intermediate metabolizers have reduced metabolism of the drug as compared to extensive metabolizers; patients with these metabolizer types may have an increased probability of experiencing side effects. Ultrarapid metabolizers break down doxepin much faster than extensive metabolizers; patients with this metabolizer type may have a greater chance of experiencing pharmacological failure.
A study assessed the metabolism of a single 75 mg oral dose of doxepin in healthy volunteers with genetic polymorphisms in CYP2D6, CYP2C9, and CYP2C19 enzymes.
Another study assessed doxepin and nordoxepin metabolism in CYP2D6 ultra-rapid, extensive, and poor metabolizers following a single 75 mg oral dose.
Doxepin is a tricyclic compound, specifically a dibenzoxepin, and possesses three rings fused together with a side chain attached in its chemical structure.
Doxepin was discovered in Germany in 1963 and was introduced in the United States as an antidepressant in 1969.
Society and culture
Generic names
Doxepin is the generic name of the drug in English and German and its INN and BAN, while doxepin hydrochloride is its USAN, USP, BANM, and JAN.
The cis or ( Z ) stereoisomer of doxepin is known as cidoxepin, and this is its INN while cidoxepin hydrochloride is its USAN.
Brand names
It was introduced under the brand names Quitaxon and Aponal by Boehringer and as Sinequan by Pfizer.
As of October 2017
The oral formulations of doxepin are FDA -approved for the treatment of depression and sleep-maintenance insomnia and its topical formulations are FDA-approved the short-term management for some itchy skin conditions.
As of 2017 there was no good evidence that topical doxepin was useful to treat localized neuropathic pain.
Cidoxepin is under development by Elorac, Inc. for the treatment of chronic urticaria (hives).
Doxepin was under development by Winston Pharmaceuticals in an intranasal formulation for the treatment of headache.

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