Medication to treat depressive disorder, anxiety disorders, chronic hives, and trouble sleeping
Doxepin Trade names Sinequan, Quitaxon, Aponal, others[ 1] Other names NSC-108160[ 2] AHFS /Drugs.com Monograph MedlinePlus a682390 License data
Pregnancy category Routes of administration By mouth , topical , intravenous , intramuscular injection [ 3] Drug class Tricyclic antidepressant (TCA)ATC code Legal status
Bioavailability 13–45% (mean 29%)[ 5] [ 6] Protein binding 76%[ 7] Metabolism Liver (CYP2D6 , CYP2C19 )[ 8] [ 5] Metabolites Nordoxepin , glucuronide conjugates[ 8] Elimination half-life Doxepin: 8–24 hours (mean 17 hours)[ 7] Nordoxepin : 28–31 hours[ 7] [ 9] Excretion Kidney : ~50%[ 8] [ 5] Feces : minor[ 5]
(E /Z )-3-(dibenzo[b ,e ]oxepin-11(6H )-ylidene)-N ,N -dimethylpropan-1-amine
CAS Number PubChem CID IUPHAR/BPS DrugBank ChemSpider UNII KEGG ChEBI ChEMBL PDB ligand CompTox Dashboard (EPA ) Formula C 19 H 21 N O Molar mass 279.383 g·mol−1 3D model (JSmol )
CN(C)CC/C=C1C2=C(C=CC=C2)OCC3=C/1C=CC=C3
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
Y Key:ODQWQRRAPPTVAG-UHFFFAOYSA-N
Y
N Y (what is this?) (verify)
Doxepin is a medication belonging to the tricyclic antidepressant (TCA)[ 10] class of drugs used to treat major depressive disorder , anxiety disorders , chronic hives , and insomnia .[ 10] [ 11] For hives it is a less preferred alternative to antihistamines .[ 10] It has a mild to moderate benefit for sleeping problems.[ 12] It is used as a cream for itchiness due to atopic dermatitis or lichen simplex chronicus .[ 13]
Common side effects include sleepiness, dry mouth, constipation , nausea, and blurry vision.[ 10] Serious side effects may include increased risk of suicide in those under the age of 25, mania , and urinary retention .[ 10] A withdrawal syndrome may occur if the dose is rapidly decreased.[ 10] Use during pregnancy and breastfeeding is not generally recommended.[ 14] [ 15] Although how it works for treating depression remains an area of active inquiry, it may involve increasing the levels of norepinephrine , along with blocking histamine , acetylcholine , and serotonin .[ 10]
Doxepin was approved for medical use in the United States in 1969.[ 10] It is available as a generic medication .[ 14] [ 16] [ 17] In 2022, it was the 218th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[ 18] [ 19]
^ Cite error: The named reference Drugs.com
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^ "Doxepin Hydrochloride" . Martindale: The Complete Drug Reference . London, UK: Pharmaceutical Press. 30 January 2013. Retrieved 3 December 2013 .
^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023 .
^ a b c d Lemke TL, Williams DA (24 January 2012). "Antidepressants" . Foye's Principles of Medicinal Chemistry . Lippincott Williams & Wilkins. pp. 604–. ISBN 978-1-60913-345-0 .
^ Cite error: The named reference pmid12162857
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^ a b c d e f g h "Doxepin Hydrochloride" . Drugs.com . American Society of Health-System Pharmacists. Retrieved 20 March 2019 .
^ "Silenor (doxepin) label" (PDF) . FDA. 17 March 2010. Retrieved 25 October 2017 . For label updates see FDA index page for NDA 022036
^ Yeung WF, Chung KF, Yung KP, Ng TH (February 2015). "Doxepin for insomnia: a systematic review of randomized placebo-controlled trials". Sleep Medicine Reviews . 19 : 75–83. doi :10.1016/j.smrv.2014.06.001 . PMID 25047681 .
^ "Doxepin hydrochloride cream" (PDF) . FDA. 20 December 2002. Retrieved 25 October 2017 . For label updates see FDA index page for NDA 020126
^ a b British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 372. ISBN 9780857113382 .
^ "Doxepin Use During Pregnancy" . Drugs.com . Retrieved 21 March 2019 .
^ "Competitive Generic Therapy Approvals" . U.S. Food and Drug Administration (FDA) . 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023 .
^ "First Generic Drug Approvals 2023" . U.S. Food and Drug Administration (FDA) . 30 May 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023 .
^ "The Top 300 of 2022" . ClinCalc . Archived from the original on 30 August 2024. Retrieved 30 August 2024 .
^ "Doxepin Drug Usage Statistics, United States, 2013 - 2022" . ClinCalc . Retrieved 30 August 2024 .