Dosulepin information

Dosulepin
Clinical data
Trade names	Prothiaden, others
Other names	IZ-914, KS-1596, dothiepin (USAN US)
AHFS/Drugs.com	International Drug Names
Pregnancy; category	AU: C; ;
Routes of; administration	Oral
ATC code	N06AA16 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only);
Pharmacokinetic data
Bioavailability	30%
Protein binding	84%
Metabolism	Hepatic (N-demethylation, S-oxidation, glucuronidation)
Metabolites	Northiaden, dothiepin sulfoxide, northiaden sulfoxide, glucuronide conjugates
Elimination half-life	Dothiepin: 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
Excretion	Urine: 56%; Feces: 15%
Identifiers
	IUPAC name (3E)-3-(6H-benzo[c][1]benzothiepin-11-ylidene)-N,N-dimethylpropan-1-amine;
CAS Number	113-53-1 113-53-1 ; HCl: 897-15-4 ;
PubChem CID	5284550;
ChemSpider	4447605 ;
UNII	W13O82Z7HL; HCl: 3H0042311V ;
KEGG	D07872 ;
ChEBI	CHEBI:36803 ;
ChEMBL	ChEMBL108947 ;
CompTox Dashboard (EPA)	DTXSID2022961 ;
ECHA InfoCard	100.003.665
Chemical and physical data
Formula	C19H21NS
Molar mass	295.44 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)CC/C=C/1\C2=CC=CC=C2CSC3=CC=CC=C31;
	InChI 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+ ; Key:PHTUQLWOUWZIMZ-GZTJUZNOSA-N ;
	(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]

^ Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
^ ^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.
^ ^a ^b Cite error: The named reference TGA was invoked but never defined (see the help page).
^ ^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.
^ Cite error: The named reference MD was invoked but never defined (see the help page).
^ 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.
^ 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.
^ Cite error: The named reference LemkeWilliams2012 was invoked but never defined (see the help page).
^ Cite error: The named reference HealCheetham1992 was invoked but never defined (see the help page).

[Elks2014-1] Cite error: The named reference Elks2014 was invoked but never defined (see the help page).

[IndexNominum2000-2] Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).

[Drugs.com-3] Cite error: The named reference Drugs.com was invoked but never defined (see the help page).

[pmid2670509-4] ^ ^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.

[TGA-5] Cite error: The named reference TGA was invoked but never defined (see the help page).

[pmid7846285-6] 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.

[MD-7] Cite error: The named reference MD was invoked but never defined (see the help page).

[pmid16390222-8] 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.

[pmid17471183-9] 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.

[LemkeWilliams2012-10] Cite error: The named reference LemkeWilliams2012 was invoked but never defined (see the help page).

[HealCheetham1992-11] Cite error: The named reference HealCheetham1992 was invoked but never defined (see the help page).

Dosulepin information

and 25 Related for: Dosulepin information

Dosulepin

Tricyclic antidepressant

Ketamine

Thiepine

Northiaden

List of antidepressants

Methylphenidate

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Duloxetine

Buprenorphine

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Antihistamine

ATC code N06

Dimenhydrinate

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Betahistine