Dosulepin

Not to be confused with Doxepin.
Dosulepin
Clinical data
Trade namesProthiaden, others
Other namesIZ-914, KS-1596[1][2][3], 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%[4]
Protein binding84%[5]
MetabolismHepatic (N-demethylation, S-oxidation, glucuronidation)[5]
MetabolitesNorthiaden, dothiepin sulfoxide, northiaden sulfoxide, glucuronide conjugates[4]
Elimination half-lifeDothiepin: 14.4–23.9 hours[4]
Dothiepin sulfoxide: 22.7–25.5 hours[4]
Northiaden: 34.7–45.7 hours[4]
Northiaden sulfoxide: 24.2–33.5 hours[4]
ExcretionUrine: 56%[4]
Feces: 15%[4]
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 Edit this at Wikidata
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
 ☒NcheckY (what is this?)  (verify)

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.[4][6][7] 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.[6][8][9] It acts as a serotonin–norepinephrine reuptake inhibitor (SNRI) and also has other activities including antihistamine, antiadrenergic, antiserotonergic, anticholinergic, and sodium channel-blocking effects.[4][10][11]

  1. ^ Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  4. ^ a b c d e f g h i j Lancaster SG, Gonzalez JP (1989). "Dothiepin. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in depressive illness". Drugs. 38 (1): 123–47. doi:10.2165/00003495-198938010-00005. PMID 2670509.
  5. ^ a b Cite error: The named reference TGA was invoked but never defined (see the help page).
  6. ^ a b Donovan S, Dearden L, Richardson L (1994). "The tolerability of dothiepin: a review of clinical studies between 1963 and 1990 in over 13,000 depressed patients". Prog. Neuropsychopharmacol. Biol. Psychiatry. 18 (7): 1143–62. doi:10.1016/0278-5846(94)90117-1. PMID 7846285. S2CID 29749302.
  7. ^ Cite error: The named reference MD was invoked but never defined (see the help page).
  8. ^ Thanacoody HK, Thomas SH (2005). "Tricyclic antidepressant poisoning : cardiovascular toxicity". Toxicol Rev. 24 (3): 205–14. doi:10.2165/00139709-200524030-00013. PMID 16390222. S2CID 44532041.
  9. ^ Gillman PK (2007). "Tricyclic antidepressant pharmacology and therapeutic drug interactions updated". Br. J. Pharmacol. 151 (6): 737–48. doi:10.1038/sj.bjp.0707253. PMC 2014120. PMID 17471183.
  10. ^ Cite error: The named reference LemkeWilliams2012 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference HealCheetham1992 was invoked but never defined (see the help page).