Structure via PubChem · Public domain (PubChem)
dothiepin
Sign in to saveAlso known as 3-dibenzo[b,e]thiepin-11(6H)-ylidene-N,N-dimethyl-1-propanamine, N,N-dimethyldibenzo[b,e]thiepin-Delta(11(6H),gamma)-propylamine, dosulepin
Dosulepin, also known as dothiepin and sold under the brand name Prothiaden among others, is a tricyclic antidepressant (TCA) which is used in the treatment of depression. Dosulepin was once the most frequently prescribed antidepressant in the United Kingdom, but it is no longer widely used due to its relatively high toxicity in overdose without therapeutic advantages over other TCAs. It acts as a serotonin–norepinephrine reuptake inhibitor (SNRI) and also has other activities including antihistamine, antiadrenergic, antiserotonergic, anticholinergic, and sodium channel-blocking effects.
Chemical data
- Formula
- C19H21NS
- Molecular weight
- 295.4 g/mol
- IUPAC name
- 3-(6H-benzo[c][1]benzothiepin-11-ylidene)-N,N-dimethylpropan-1-amine
- SMILES
- CN(C)CCC=C1C2=CC=CC=C2CSC3=CC=CC=C31
- InChIKey
- PHTUQLWOUWZIMZ-UHFFFAOYSA-N
- XLogP
- 4.5
- Polar surface area
- 28.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
427 papers- Dothiepin.2006
- Dothiepin. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in depressive illness.Drugs · 1989
- Dose equivalents of antidepressants: Evidence-based recommendations from randomized controlled trials.Journal of affective disorders · 2015
- The excretion of dothiepin and its primary metabolites in breast milk.British journal of clinical pharmacology · 1992
- Misuse of dothiepin.BMJ (Clinical research ed.) · 1995
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 295.139
Show 4 more facts
- canonical SMILES
- CN(C)CCC=C1C2=CC=CC=C2CSC3=CC=CC=C31
- chemical formula
- C₁₉H₂₁NS
- isomeric SMILES
- CN(C)CC/C=C\1/C2=CC=CC=C2CSC3=C1C=CC=C3
- Commons category
- Dosulepin
Sources (2)
via Wikidata · CC0
~10 min read
Encyclopedic overview
15 sectionsContents
- Medical uses
- Contraindications
- Side effects
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Generic names
- Brand names
- Availability
- References
Dosulepin, also known as dothiepin and sold under the brand name Prothiaden among others, is a tricyclic antidepressant (TCA) which is used in the treatment of depression. Dosulepin was once the most frequently prescribed antidepressant in the United Kingdom, but it is no longer widely used due to its relatively high toxicity in overdose without therapeutic advantages over other TCAs. It acts as a serotonin–norepinephrine reuptake inhibitor (SNRI) and also has other activities including antihistamine, antiadrenergic, antiserotonergic, anticholinergic, and sodium channel-blocking effects.
==Medical uses== Dosulepin is used for the treatment of major depressive disorder. There is clear evidence of the efficacy of dosulepin in psychogenic facial pain, though the drug may be needed for up to a year.
Excerpted from Wikipedia’s “dothiepin” article, available under the CC BY-SA 4.0 licence.