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QuickView for Doxepin (compound)


PubChem
Name: Doxepin
PubChem Compound ID: 10039438
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.
Molecular formula: C19H21NO
Molecular weight: 282.395 g/mol
DrugBank
Identification
Name: Doxepin
Name (isomeric): DB01142
Drug Type: small molecule
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.
Synonyms:
Doxepine; Doxepinum [INN-Latin]; Doxepina [INN-Spanish]; Doxepin, Hydrochloride; Doxepin Hcl
Brand: Adapin, Zonalon, Triadapin, Quitaxon, Sinequan, Curatin, Aponal
Category: Norepinephrine-Reuptake Inhibitors, Antidepressants, Histamine Antagonists, Anti-anxiety Agents, Antipruritics, Antidepressive Agents, Tricyclic
CAS number: 1668-19-5
Pharmacology
Indication: Labeled indications: depression and insomnia. Unlabeled indications: chronic and neuropathic pain, anxiety, idiopathic urticaria.
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.
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 H1-receptors, resulting in sedative effects, and β-adrenergic receptors.
Absorption: Well-absorbed from the GI tract. Peak plasma concentrations occur within 2 hours of oral administration.
Protein binding: Highly bound to plasma proteins.
Biotransformation: Extensively metabolized in the liver via the same pathways as other TCAs. N-demethylation produces an active metabolite, N-desmethyldoxepin.
Half Life: 6 - 24.5 hours
Toxicity: LD50=26 (mg/kg) (in mice, iv); LD50=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. Side effects include: sedation, hypotension, blurred vision, dry mouth, constipation, urinary retention, postural hypotension, tachycardia, hypertension, ECG changes, heart failure, impaired memory and delirium, and precipitation of hypomanic or manic episodes in bipolar depression. Withdrawal symptoms include gastrointestinal disturbances, anxiety, and insomnia.
Affected organisms: Humans and other mammals
Interactions
Food interaction:
Avoid St.John's Wort.
Avoid alcohol.
Take with food to reduce irritation.
Avoid excessive quantities of coffee or tea (caffeine).
Drug interaction:
GrepafloxacinIncreased risk of cardiotoxicity and arrhythmias
ButalbitalBarbiturates such as butalbital may increase the metabolism of tricyclic antidepressants such as doxepin. Monitor for decreased therapeutic effects of tricyclic antidepressants if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. The tricyclic antidepressant dosage will likely need to be increased during concomitant barbiturate therapy, and reduced upon barbiturate discontinuation.
FenoterolThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of fenoterol.
RitonavirRitonavir may increase the effect and toxicity of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if ritonavir if initiated, discontinued or dose changed.
ButabarbitalBarbiturates like butabarbital may increase the metabolism of tricyclic antidepressants like doxepin. Monitor for decreased therapeutic effects of tricyclic antidepressants if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. The tricyclic antidepressant dosage will likely need to be increased during concomitant barbiturate therapy, and reduced upon barbiturate discontinuation.
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