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+
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 Date-8.64E9 |
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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 Date-8.64E9 |
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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 Date7.6515842E11 |
PubMed
Title | Date | PubMed |
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A review of clinical studies with combinations of fluphenazine and nortriptyline. | 1972 |
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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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A controlled comparison of doxepin h.s. and doxepin q.i.d. | 1975 Jul |
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Delirium associated with sulindac. | 1980 Apr 25 |
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A comparative study of the therapeutic effect and cardiotoxicity of dothiepin HCl and doxepin HCl in reactive depression. | 1981 |
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Transient ophthalmoparesis with doxepin overdosage. | 1981 Jun |
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Doxepin and visual hallucinations. | 1982 Dec |
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Doxepin induced torsade de pointes. | 1982 Nov |
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Orthostatic effect of imipramine and doxepin in depressed geriatric outpatients. | 1985 Apr |
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Alprazolam, amitriptyline, doxepin, and placebo in the treatment of depression. | 1985 Feb |
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A comparative trial of the antidepressant, anxiolytic, and cardiovascular effects of trimipramine and doxepin in depressed hospitalized patients. | 1985 Mar |
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Seizures with neuroleptics and antidepressants. | 1987 Mar |
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Dystonic reactions to amitriptyline and doxepin. | 1988 May |
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Doxepin in the treatment of female detrusor overactivity: a randomized double-blind crossover study. | 1989 Oct |
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Protracted ventricular arrhythmias occurring after abrupt tricyclic antidepressant withdrawal. | 1990 Fall |
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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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[Valproic acid in prophylaxis of bipolar disorder. A case of valproate-induced encephalopathy]. | 2000 May |
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Influence of doxepin used in preemptive analgesia on the nociception in the perioperative period. Experimental and clinical study. | 2001 May-Jun |
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Doxepin-induced torsade de pointes tachycardia. | 2001 Sep 4 |
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Prescription of QT-prolonging drugs in a cohort of about 5 million outpatients. | 2003 Feb 1 |
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Differential enhancement of antidepressant penetration into the brain in mice with abcb1ab (mdr1ab) P-glycoprotein gene disruption. | 2003 Oct 15 |
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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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Frequency of high-risk use of QT-prolonging medications. | 2006 Jun |
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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.
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851NLB57HQ
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3607-34-9
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667477
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)