Dosulepin

Structural formula
	cis -form (top) and trans -form (bottom)
General
Non-proprietary name	Dosulepin
other names	11- (3-Dimethylaminopropylidene) -6,11-dihydrodibenz [ b , e ] thiepin ( IUPAC ) ; Dothiepin ( BAN ) ;
Molecular formula	C 19 H 21 NS (Dosulepin) ; C 19 H 21 NS · HCl (Dosulepin · Hydrochloride ) ;
Brief description	white to pale yellow, crystalline powder (Dosulepin hydrochloride)
External identifiers / databases
EC number	204-031-2
ECHA InfoCard	100.003.665
PubChem	3155
ChemSpider	3043
Wikidata	Q27116967
Drug information
ATC code	N06 AA16
Drug class	Tricyclic antidepressant
properties
Molar mass	295.45 g mol −1 (Dosulepin) ; 331.92 g mol −1 (dosulepin hydrochloride) ;
solubility	Easily soluble in water, dichloromethane and ethanol (Dosulepin hydrochloride)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Hydrochloride; Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	260 mg kg −1 ( LD 50 , rat , oral , hydrochloride)
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dosulepin ( INN ) is a drug from the group of tricyclic antidepressants . It is a mixture of cis - and trans - isomer usually used as the hydrochloride.

pharmacology

Pharmacodynamics and pharmacokinetics

Dosulepin has the same effect as Doxepin . It inhibits the reuptake of the neurotransmitters serotonin and norepinephrine , besides it also acts as an antagonist at histamine H ₁ - and muscarinic receptor . It has a bioavailability of 30% and a half-life of 20 hours. It is metabolized via the liver.

Side effects

Common side effects (<1%) are: nausea, headache, constipation , dry mouth, sweating, dizziness, drowsiness, gastrointestinal disorders, subtle tremor.

In the event of an overdose, Dosulepin is more toxic than other tricyclics and leads to increased seizures and cardiac arrhythmias.

Indications

Dosulepin is approved for the treatment of inhibited depression . It is used off-label for adjuvant therapy for chronic pain . Therapeutically sensible doses range between 75 and 150 mg daily, in-patient treatment can be increased up to 300 mg if necessary. There is a relative contraindication in patients with cardiovascular disease.

Trade names

Monopreparations

Idom (D; since 2014 out of trade), Prothiaden (in some European countries)

Combination preparations

with Diazepam : Harmomed (A) no longer available (September 2016)

Individual evidence

↑ ^a ^b ^c Datasheet DOSULEPIN HYDROCHLORIDE CRS (PDF) at EDQM , accessed on December 3, 2009.
↑ ^a ^b data sheet Dothiepin hydrochloride from Sigma-Aldrich , accessed on April 29, 2011 ( PDF ).
^ NA Buckley, AH Dawson, IM Whyte, DA Henry: Greater toxicity in overdose of dothiepin than of other tricyclic antidepressants. In: The Lancet . Volume 343, Number 8890, January 1994, pp. 159-162, doi : 10.1016 / s0140-6736 (94) 90940-7 , PMID 7904010 .
↑ Benkert, Hippius (ed.): Compendium of psychiatric pharmacotherapy. 6th edition, Springer, Berlin 2007. p. 87. ISBN 3-540-21893-9 .
↑ When drugs are misused. August 13, 2015, accessed December 20, 2019 .
↑ Index Nominum, online version.
↑ AGES-PharmMed, as of June 2010.

[Ph._Eur.-1] Datasheet DOSULEPIN HYDROCHLORIDE CRS (PDF) at EDQM , accessed on December 3, 2009.

[Sigma-2] ta sheet Dothiepin hydrochloride from Sigma-Aldrich , accessed on April 29, 2011 ( PDF ).

[3] NA Buckley, AH Dawson, IM Whyte, DA Henry: Greater toxicity in overdose of dothiepin than of other tricyclic antidepressants. In: The Lancet . Volume 343, Number 8890, January 1994, pp. 159-162, doi : 10.1016 / s0140-6736 (94) 90940-7 , PMID 7904010 .

[4] Benkert, Hippius (ed.): Compendium of psychiatric pharmacotherapy. 6th edition, Springer, Berlin 2007. p. 87. ISBN 3-540-21893-9 .

[5] When drugs are misused. August 13, 2015, accessed December 20, 2019 .

[6] Index Nominum, online version.

[7] AGES-PharmMed, as of June 2010.