Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H21NO |
Molecular Weight | 279.3761 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CC\C=C1/C2=C(COC3=C1C=CC=C3)C=CC=C2
InChI
InChIKey=ODQWQRRAPPTVAG-GZTJUZNOSA-N
InChI=1S/C19H21NO/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3/b17-11+
Molecular Formula | C19H21NO |
Molecular Weight | 279.3761 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11465523 | https://www.drugs.com/monograph/doxepin-hydrochloride.html | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aa69c63c-ced6-4676-a16b-554f1af7d210
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11465523 | https://www.drugs.com/monograph/doxepin-hydrochloride.html | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aa69c63c-ced6-4676-a16b-554f1af7d210
Doxepin is a dibenzoxepin tricyclic antidepressant marketed worldwide. It is a white crystalline solid readily soluble in water, lower alcohols and chloroform. The mechanism of action of doxepin is not definitely known. It is not a central nervous system stimulant nor a monoamine oxidase inhibitor. The current hypothesis is that the clinical effects are due, at least in part, to influences on the adrenergic activity at the synapses so that deactivation of norepinephrine by reuptake into the nerve terminals is prevented. Antidepressants may increase risk of suicidal thinking and behavior (suicidality) in children, adolescents, and young adults (18–24 years of age) with major depressive disorder and other psychiatric disorders. Drowsiness is the most commonly noticed side effect. This tends to disappear as therapy is continued. Other infrequently reported CNS side effects are confusion, disorientation, hallucinations, numbness, paresthesias, ataxia, extrapyramidal symptoms, seizures, tardive dyskinesia, and tremor. : Cardiovascular effects including hypotension, hypertension, and tachycardia have been reported occasionally. Skin rash, edema, photosensitization, and pruritus have occasionally occurred. Eosinophilia has been reported in a few patients. There have been occasional reports of bone marrow depression manifesting as agranulocytosis, leukopenia, thrombocytopenia, and purpura. Doxepin is used to treat depression, anxiety disorders, itchiness, trouble sleeping, and as a second-line treatment of chronic idiopathic urticaria (hives). Its oral formulations are FDA-approved for the treatment of depression, anxiety, and insomnia and its topical formulations are FDA-approved the short-term management (up to 8 days) of atopic dermatitis and lichen simplex chronicus. Whereas in Australia and the UK, the only licensed indication(s) is/are in the treatment of major depression and pruritus in eczema, respectively.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12360109 |
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Target ID: GO:0098810 |
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Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | SINEQUAN Approved UseINDICATIONS & USAGE Doxepin is recommended for the treatment of: Psychoneurotic patients with depression and/or anxiety. Depression and/or anxiety associated with alcoholism (not to be taken concomitantly with alcohol). Depression and/or anxiety associated with organic disease (the possibility of drug interaction should be considered if the patient is receiving other drugs concomitantly). Psychotic depressive disorders with associated anxiety including involutional depression and manic-depressive disorders. The target symptoms of psychoneurosis that respond particularly well to doxepin include anxiety, tension, depression, somatic symptoms and concerns, sleep disturbances, guilt, lack of energy, fear, apprehension and worry. Clinical experience has shown that doxepin is safe and well tolerated even in the elderly patient. Owing to lack of clinical experience in the pediatric population, doxepin is not recommended for use in children under 12 years of age. Launch Date1969 |
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Primary | SINEQUAN Approved UseINDICATIONS & USAGE Doxepin is recommended for the treatment of: Psychoneurotic patients with depression and/or anxiety. Depression and/or anxiety associated with alcoholism (not to be taken concomitantly with alcohol). Depression and/or anxiety associated with organic disease (the possibility of drug interaction should be considered if the patient is receiving other drugs concomitantly). Psychotic depressive disorders with associated anxiety including involutional depression and manic-depressive disorders. The target symptoms of psychoneurosis that respond particularly well to doxepin include anxiety, tension, depression, somatic symptoms and concerns, sleep disturbances, guilt, lack of energy, fear, apprehension and worry. Clinical experience has shown that doxepin is safe and well tolerated even in the elderly patient. Owing to lack of clinical experience in the pediatric population, doxepin is not recommended for use in children under 12 years of age. Launch Date1969 |
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Primary | ZONALON Approved UseINDICATIONS & USAGE Zonalon Cream is indicated for the short-term (up to 8 days) management of moderate pruritus in adult patients with atopic dermatitis or lichen simplex chronicus. Launch Date1994 |
PubMed
Title | Date | PubMed |
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Effect of beta-adrenoceptor blocking drugs, physostigmine, and atropine on the toxicity of doxepin in mice. | 1975 Aug |
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Tricyclic-induced myoclonus. | 1977 Jan |
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Doxepin in the treatment of female detrusor overactivity: a randomized double-blind crossover study. | 1989 Oct |
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Serious adverse effects of combining fluoxetine and tricyclic antidepressants. | 1990 Apr |
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Protracted ventricular arrhythmias occurring after abrupt tricyclic antidepressant withdrawal. | 1990 Fall |
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Effect of IAP and chronic antidepressant administration on the 5HT1A receptor in rat cortical membranes. | 1992 May |
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Bupropion-induced carbohydrate craving and weight gain. | 1992 Oct |
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Doxepin-induced recurrent acute hepatitis. | 1993 Oct |
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Pharmacological profile of antidepressants and related compounds at human monoamine transporters. | 1997 Dec 11 |
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Electrocardiographic effects of fluoxetine and doxepin in patients with major depressive disorder. | 1997 Feb |
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Focal cortical transient preceding myoclonus during lithium and tricyclic antidepressant therapy. | 1999 Jan 1 |
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Prescription of QT-prolonging drugs in a cohort of about 5 million outpatients. | 2003 Feb 1 |
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'Hypnotic' prescription patterns in a large managed-care population. | 2004 Sep |
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Antidepressant-associated chronic irritable dysphoria (acid) in bipolar disorder: a case series. | 2005 Feb |
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[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations]. | 2006 Jun |
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Identification of human Ether-à-go-go related gene modulators by three screening platforms in an academic drug-discovery setting. | 2010 Dec |
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Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20126slr006_Zonalon_lbl.pdf
For Mild Anxiety: Initial dose: 25 mg per day in 1 to 3 divided doses. Maintenance dose: 25 to 50 mg per day in 1 to 3 divided doses.
For Moderate Anxiety: Initial dose: 75 mg per day in 1 to 3 divided doses. Maintenance dose: 75 to 150 mg per day in 1 to 3 divided doses.
For Severe Anxiety: Initial dose: 150 mg per day in 1 to 3 divided doses. Maintenance dose: 150 to 300 mg per day in 1 to 3 divided doses.
The maximum single dose should not exceed 150 mg.
For treatment moderate pruritus
A thin film of Doxepin should be applied four times each day with at least a 3 to 4 hour interval between applications. There are no data to establish the safety and effectiveness of Doxepin when used for greater than 8 days. Chronic use beyond eight days may result in higher systemic levels and should be avoided.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9044238
Doxepin effects were studied on rat vas deferens responses to noradrenaline. Tissues were prepared in Krebs-Henseleit solution. In normal Krebs-Henseleit solution doxepin behaved as competitive antagonists.
Substance Class |
Chemical
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