Doxepin

Not to be confused with Dosulepin.

Doxepin
Clinical data
Trade namesSinequan, Quitaxon, Aponal, others[1]
Other namesNSC-108160[2]
AHFS/Drugs.comMonograph
MedlinePlusa682390
License data
Pregnancy
category
  • AU: C
Routes of
administration		By mouth, topical, intravenous, intramuscular injection[3]
Drug classTricyclic antidepressant (TCA)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability13–45% (mean 29%)[5][6]
Protein binding76%[7]
MetabolismLiver (CYP2D6, CYP2C19)[8][5]
MetabolitesNordoxepin, glucuronide conjugates[8]
Elimination half-lifeDoxepin: 8–24 hours (mean 17 hours)[7]
Nordoxepin: 28–31 hours[7][9]
ExcretionKidney: ~50%[8][5]
Feces: minor[5]
Identifiers
  • (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)
Chemical and physical data
FormulaC19H21NO
Molar mass279.383 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 checkY
  • Key:ODQWQRRAPPTVAG-UHFFFAOYSA-N checkY
 ☒NcheckY (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 2020, it was the 252nd most commonly prescribed medication in the United States, with more than 1 million prescriptions.[18][19]

  1. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
  3. ^ "Doxepin Hydrochloride". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. 30 January 2013. Retrieved 3 December 2013.
  4. ^ Anvisa (2023-03-31). "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 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  5. ^ 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.
  6. ^ Cite error: The named reference pmid12162857 was invoked but never defined (see the help page).
  7. ^ a b c Cite error: The named reference EMC was invoked but never defined (see the help page).
  8. ^ a b c Cite error: The named reference pmid20658801 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference pmid7293791 was invoked but never defined (see the help page).
  10. ^ a b c d e f g h "Doxepin Hydrochloride". Drugs.com. American Society of Health-System Pharmacists. Retrieved 20 March 2019.
  11. ^ "Silenor (doxepin) label" (PDF). FDA. 17 March 2010. Retrieved 25 October 2017. For label updates see FDA index page for NDA 022036
  12. ^ 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.
  13. ^ "Doxepin hydrochloride cream" (PDF). FDA. 20 December 2002. Retrieved 25 October 2017. For label updates see FDA index page for NDA 020126
  14. ^ a b British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 372. ISBN 9780857113382.
  15. ^ "Doxepin Use During Pregnancy". Drugs.com. Retrieved 21 March 2019.
  16. ^ "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.
  17. ^ "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.
  18. ^ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  19. ^ "Doxepin - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.