Dosulepin

Dosulepin

Clinical data
Trade names	Dothep, Prothiaden
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) US: ℞-only
Pharmacokinetic data
Bioavailability	30%
Protein binding	84%
Metabolism	Hepatic (via N-demethylation to active metabolite northiaden, S-oxidation and glucuronidation)
Biological half-life	51 hours, 14-45 hours, 54 hours (elderly)
Excretion	Urine (56%), faeces (15%)
Identifiers
IUPAC name (E,Z)-3-(dibenzo[b,e]thiepin-11(6H)-ylidene)-N,N-dimethylpropan-1-amine
CAS Number	113-53-1 Y
PubChem CID	13473
ChemSpider	4447605 N
UNII	W13O82Z7HL
KEGG	D07872 Y
ChEMBL	CHEMBL108947 N
ECHA InfoCard	100.003.665
Chemical and physical data
Formula	C19H21NS
Molar mass	295.45 g/mol
3D model (Jmol)	Interactive image
SMILES CN(C)CC/C=C/1\c2ccccc2CSc3c1cccc3
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+ N Key:PHTUQLWOUWZIMZ-GZTJUZNOSA-N N
NY (what is this?)

Dosulepin (INN, BAN) formerly known as dothiepin (USAN), and marketed under the brand names Prothiaden, Dothep, Thaden, and Dopress, is a tricyclic antidepressant that is used in several European and South Asian countries, as well as Australia, South Africa, and New Zealand. It is not used in the United States.

Dosulepin is used for the treatment of major depressive disorder and neuropathic pain. Dosulepin is only TGA- and MHRA-approved 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.

Common adverse effects:

Less common adverse effects:

Contraindications include:

Dosulepin can potentiate the effects of alcohol and at least one death has been attributed to this combination. TCAs potentiate the sedative effects of barbiturates, tranquillisers and CNS depressants.Guanethidine and other adrenergic neurone blocking drugs can have their antihypertensive effects blocked by dosulepin. Sympathomimetics may potentiate the sympathomimetic effects of dosulepin. Due to the anticholinergic and antihistamine effects of dosulepin anticholinergic and antihistamine medications may have their effects potentiated by dosulepin and hence these combinations are advised against. Dosulepin may have its postural hypotensive effects potentiated by diuretics. Anticonvulsants may have their efficacy reduced by dosulepin due to its ability to reduce the seizure threshold.