Structure via PubChem · Public domain (PubChem)
(E/Z)-doxepin
Sign in to saveDoxepin is a medication belonging to the tricyclic antidepressant (TCA) class of drugs used to treat major depressive disorder, anxiety disorders, difficult-to-treat chronic urticaria, and insomnia. For hives it is a less preferred alternative to antihistamines. It has a mild to moderate benefit for sleeping problems. It is used as a cream for itchiness due to atopic dermatitis or lichen simplex chronicus.
Key facts
- Drug.class
- Tricyclic antidepressant (TCA)
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 459441838
- Drug.image
- Doxepin-2D-skeletal.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 175
- Drug.image2
- Doxepin-3RZE-2011-ball-and-stick.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 175
- Drug.tradename
- Silenor, others
- Drug.MedlinePlus
- a682390
- Drug.DailyMedID
- Doxepin
- Drug.pregnancy_AU
- C
- Drug.routes_of_administration
- By mouth, topical, intravenous, intramuscular injection
- Drug.ATC_prefix
- D04
- Drug.ATC_suffix
- AX01
- Drug.legal_AU
- S4
via Wikipedia infobox
Chemical data
- Formula
- C19H21NO
- Molecular weight
- 279.4 g/mol
- IUPAC name
- 3-(6H-benzo[c][1]benzoxepin-11-ylidene)-N,N-dimethylpropan-1-amine
- SMILES
- CN(C)CCC=C1C2=CC=CC=C2COC3=CC=CC=C31
- InChIKey
- ODQWQRRAPPTVAG-UHFFFAOYSA-N
- XLogP
- 4.3
- Polar surface area
- 12.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
4 papers- Binding characteristics of the doxepin E/Z-isomers to the histamine H(1) receptor revealed by receptor-bound ligand analysis and molecular dynamics study.Journal of molecular recognition : JMR · 2024
- Contributions of CYP2D6, CYP2C9 and CYP2C19 to the biotransformation of E- and Z-doxepin in healthy volunteers.Pharmacogenetics · 2002
- Stereoselective measurement of E- and Z-doxepin and its N-desmethyl and hydroxylated metabolites by gas chromatography-mass spectrometry.Journal of chromatography. B, Biomedical sciences and applications · 1999
- Separation of (Z)- and (E)-isomers of thioxanthene and dibenz[b,e]oxepin derivatives with calixarenes and resorcinarenes as additives in nonaqueous capillary electrophoresis.Electrophoresis · 2003
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 279.162314292
Show 6 more facts
- has characteristic
- bitterness
- stylized name
- SINEquan
- Commons category
- Doxepin
- canonical SMILES
- CN(C)CCC=C1c2ccccc2COc2ccccc21
- chemical formula
- C₁₉H₂₁NO
- significant drug interaction
- loxapine
via Wikidata · CC0
~29 min read
Encyclopedic overview
30 sectionsContents
- Medical uses
- Insomnia
- Other uses
- Contraindications
- Pregnancy and lactation
- Side effects
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- As a hypnotic
- CYP2D6 inhibition
- Pharmacokinetics
- Absorption
- Distribution
- Metabolism
- Elimination
- Pharmacogenetics
- Chemistry
- History
- Society and culture
- Generic names
- Brand names
- Approvals
- Research
- Antihistamine
- Headache
- Neuropathic pain
- References
- External links
Doxepin is a medication belonging to the tricyclic antidepressant (TCA) class of drugs used to treat major depressive disorder, anxiety disorders, difficult-to-treat chronic urticaria, and insomnia. For hives it is a less preferred alternative to antihistamines. It has a mild to moderate benefit for sleeping problems. It is used as a cream for itchiness due to atopic dermatitis or lichen simplex chronicus.
Common side effects include sleepiness, dry mouth, constipation, nausea, and blurry vision. Serious side effects may include increased risk of suicide in those under the age of 25, mania, and urinary retention. A withdrawal syndrome may occur if the dose is rapidly decreased. Use during pregnancy and breastfeeding is not generally recommended. 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.
Excerpted from Wikipedia’s “(E/Z)-doxepin” article, available under the CC BY-SA 4.0 licence.