Dothiepin

Title: Dothiepin
CAS Registry Number: 113-53-1
CAS Name: 3-Dibenzo[b,e]thiepin-11(6H)-ylidene-N,N-dimethyl-1-propanamine
Additional Names: N,N-dimethyldibenzo[b,e]thiepin-D11(6H),g-propylamine; 11-(3-dimethylaminopropylidene)-6,11-dihydrodibenzo[b,e]thiepin; dosulepin
Molecular Formula: C19H21NS
Molecular Weight: 295.44
Percent Composition: C 77.24%, H 7.16%, N 4.74%, S 10.85%
Literature References: Tricyclic antidepressant. Prepn: M. Protiva et al., Experientia 18, 326 (1962); BE 618591; M. Protiva et al., US 3527766 (1962, 1970 both to SPOFA); M. Rajsner, M. Protiva, Cesk. Farm. 11, 404 (1962), C.A. 59, 2772g (1963). Synthesis of isomers: M. Rajsner et al., Collect. Czech. Chem. Commun. 34, 1963 (1969). Pharmacology: J. Metysova et al., Arzneim.-Forsch. 13, 1039 (1963). Clinical pharmacokinetics and metabolism: K. P. Maguire et al., Br. J. Clin. Pharmacol. 12, 405 (1981). HPLC determn in plasma: P. J. Taylor et al., J. Chromatogr. 581, 152 (1992). Review of clinical experience in depression: S. Donovan et al., Prog. Neuro-Psychopharmacol. Biol. Psychiatry 18, 1143-1162 (1994).
Properties: bp0.05 171-172°. mp 55-57°.
Melting point: mp 55-57°
Boiling point: bp0.05 171-172°
Derivative Type: Hydrochloride
CAS Registry Number: 897-15-4
Trademarks: Prothiaden (Knoll)
Molecular Formula: C19H21NS.HCl
Molecular Weight: 331.90
Percent Composition: C 68.76%, H 6.68%, N 4.22%, S 9.66%, Cl 10.68%
Properties: Crystals from ethanol-ether, mp 218-221°. uv max (methanol): 232, 260, 309 nm (log e 4.41, 3.97, 3.53).
Melting point: mp 218-221°
Absorption maximum: uv max (methanol): 232, 260, 309 nm (log e 4.41, 3.97, 3.53)
Therap-Cat: Antidepressant.
Keywords: Antidepressant; Tricyclics.
Dowicide 9? Doxacurium Chloride Doxapram Doxazosin Doxefazepam

Dosulepin
Dosulepin2DACS2.svg
Dosulepin3Dan.gif
Systematic (IUPAC) name
(E,Z)-3-(dibenzo[b,e]thiepin-11(6H)-ylidene)-N,N-dimethylpropan-1-amine
Clinical data
Trade names Dothep, Prothiaden
AHFS/Drugs.com International Drug Names
Pregnancy cat. C (AU)
Legal status Prescription Only (S4) (AU) POM (US)
Routes Oral
Pharmacokinetic data
Bioavailability 30%[1]
Protein binding 84%[2]
Metabolism Hepatic (via N-demethylation to active metabolite northiaden, S-oxidation and glucuronidation)[2]
Half-life 51 hours,[2] 14-45 hours,[3][4][5] 54 hours (elderly)[5][6]
Excretion Urine (56%), faeces (15%)[2]
Identifiers
CAS number 113-53-1 YesY
ATC code N06AA16
PubChem CID 13473
UNII W13O82Z7HL YesY
KEGG D07872 YesY
ChEMBL CHEMBL108947 N
Chemical data
Formula C19H21NS 
Mol. mass 295.45 g/mol
 N (what is this?)  (verify)

Dosulepin (INN, BAN) formerly known as dothiepin (USAN) and by the brand names Prothiaden, Dothep, Thaden and Dopress. Dosulepin is a tricyclic antidepressant that is used in a few European and South Asian countries as well as Australia South Africa and New Zealand. It is not used in the United States.[7]