Bisulepin

Chemical compound

R06AX (WHO)

Identifiers

IUPAC name

(3E)-N,N-dimethyl-3-(thieno[2,3-c][2]benzothiepin-4(9H)-ylidene)propan-1-amine

CAS Number

42504-83-6

PubChem CID

6537425

ChemSpider

5020597

UNII

595726R32U

ChEBI

CHEBI:135277

CompTox Dashboard (EPA)

DTXSID301336166 DTXSID40973608, DTXSID301336166

ECHA InfoCard100.024.867

Chemical and physical dataFormulaC₁₇H₁₉NS₂Molar mass301.47 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

CN(C)CC\C=C1\c2ccsc2SCc2ccccc12

Bisulepin is strong and relatively selective antihistamine (H₁ antagonist) with hypnotic, antiadrenergic and very weak anticholinergic and antiserotonergic effects. Bisulepin is marketed in the Czech Republic and Slovakia under the trademark Dithiaden as tablets and injections.

The registered active form is the trans- (i.e. E-) isomer.^[1]^[2]

References

^ Polívka Z, Rajšner M, Metyš J, Holubek J, Svátek E, Ryska M, Protiva M (1983). "Antiaminic agents derived from thieno[2,3-c]-2-benzothiepin: 4-(1-Methyl-4-piperidylidene)-4,9-dihydrothieno[2,3-c]-2-benzothiepin and some related compounds". Collection of Czechoslovak Chemical Communications. 48 (2): 623–641. doi:10.1135/cccc19830623.
^ Pharmacopoea Bohemoslovenica 4 (1987), vol. 2, p. 132 states that Bisulepinium chloratum (bisulepinium chloride) is trans-[3-(4,9-dihydro-thieno[2,3-c][2]benzithiepin-4-yliden)propyl]dimethylamoniumchlorid (Czech). The cis- isomer is considered as an impurity, max. amount 2.0 %.