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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
Structure of DOXEPIN, (E)-

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+

HIDE SMILES / InChI

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

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SINEQUAN

Approved Use

INDICATIONS & 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
Primary
SINEQUAN

Approved Use

INDICATIONS & 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
Primary
ZONALON

Approved Use

INDICATIONS & 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 Date

7.6515842E11
PubMed

PubMed

TitleDatePubMed
A controlled comparison of doxepin h.s. and doxepin q.i.d.
1975 Jul
Comparison of the cardiovascular toxicity of three tricyclic antidepressant drugs: imipramine, amitriptyline, and doxepin.
1979 Mar
Delirium associated with sulindac.
1980 Apr 25
Doxepin and visual hallucinations.
1982 Dec
Doxepin induced torsade de pointes.
1982 Nov
Therapeutic superiority of maprotiline versus doxepin in geriatric depression.
1983 Dec
Bilateral internuclear ophthalmoplegia from doxepin overdose.
1984 Feb
Pharmacological profile of antidepressants and related compounds at human monoamine transporters.
1997 Dec 11
Electrocardiographic effects of fluoxetine and doxepin in patients with major depressive disorder.
1997 Feb
The addition of topical doxepin to corticosteroid therapy: an improved treatment regimen for atopic dermatitis.
1999 Feb
Antidepressants upregulate messenger RNA levels of the neuroprotective enzyme superoxide dismutase (SOD1).
2000 Jan
[Valproic acid in prophylaxis of bipolar disorder. A case of valproate-induced encephalopathy].
2000 May
Doxepin-induced torsade de pointes tachycardia.
2001 Sep 4
'Hypnotic' prescription patterns in a large managed-care population.
2004 Sep
QT prolongation and syncope with methadone, doxepin, and a beta-blocker.
2005 Oct
[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
Frequency of high-risk use of QT-prolonging medications.
2006 Jun
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

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
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
Created
by admin
on Fri Dec 15 15:59:02 UTC 2023
Edited
by admin
on Fri Dec 15 15:59:02 UTC 2023
Record UNII
851NLB57HQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOXEPIN, (E)-
Common Name English
(3E)-3-DIBENZO(B,E)OXEPIN-11(6H)-YLIDENE-N,N-DIMETHYLPROPAN-1-AMINE
Systematic Name English
DOXEPIN, E-ISOMER
Common Name English
1-PROPANAMINE, 3-DIBENZ(B,E)OXEPIN-11(6H)-YLIDENE-N,N-DIMETHYL-, (3E)-
Systematic Name English
Code System Code Type Description
FDA UNII
851NLB57HQ
Created by admin on Fri Dec 15 15:59:02 UTC 2023 , Edited by admin on Fri Dec 15 15:59:02 UTC 2023
PRIMARY
CAS
3607-34-9
Created by admin on Fri Dec 15 15:59:02 UTC 2023 , Edited by admin on Fri Dec 15 15:59:02 UTC 2023
PRIMARY
PUBCHEM
667477
Created by admin on Fri Dec 15 15:59:02 UTC 2023 , Edited by admin on Fri Dec 15 15:59:02 UTC 2023
PRIMARY
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