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.

Not to be confused with Doxepin.
Dosulepin
Clinical data
Trade namesProthiaden, others
Other namesIZ-914, KS-1596, dothiepin (USAN US)
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • AU: C
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
Pharmacokinetic data
Bioavailability30%
Protein binding84%
MetabolismHepatic (N-demethylation, S-oxidation, glucuronidation)
MetabolitesNorthiaden, dothiepin sulfoxide, northiaden sulfoxide, glucuronide conjugates
Elimination half-lifeDothiepin: 14.4–23.9 hours
Dothiepin sulfoxide: 22.7–25.5 hours
Northiaden: 34.7–45.7 hours
Northiaden sulfoxide: 24.2–33.5 hours
ExcretionUrine: 56%
Feces: 15%
Identifiers
  • (3E)-3-(6H-benzo[c][1]benzothiepin-11-ylidene)-N,N-dimethylpropan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.003.665
Chemical and physical data
FormulaC19H21NS
Molar mass295.44 g·mol−1
3D model (JSmol)
  • CN(C)CC/C=C/1\C2=CC=CC=C2CSC3=CC=CC=C31
  • InChI=1S/C19H21NS/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+ N
  • Key:PHTUQLWOUWZIMZ-GZTJUZNOSA-N N
 NY (what is this?)  (verify)
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