Dosulepin hydrochlorideProduct ingredient for Dosulepin

Name
Dosulepin hydrochloride
Drug Entry
Dosulepin

Dosulepin (INN, BAN) formerly known as dothiepin (USAN), is a tricyclic antidepressant with anxiolytic properties that is used in several European and South Asian countries, as well as Australia, South Africa, and New Zealand. It is not FDA-approved due to low therpeutic index and significant toxicity in overdose. Dosulepin inhibits the reuptake of biogenic amines, increasing available neurotransmitter levels at the synaptic cleft. The use of dosulepsin is only recommended in patients who are intolerant or unresponsive to alternative antidepressant therapies. Dosulepsin is a thio derivative of Amitriptyline with a similar efficacy to that of Amitriptyline, and also exhibits anticholinergic, antihistamine and central sedative properties 8. Its hydrochloride form is a common active ingredient in different drug formulations.

Accession Number
DBSALT001822
Structure
Synonyms
Dosulepin HCl / Dothiepin HCl / Dothiepin hydrochloride
UNII
3H0042311V
CAS Number
897-15-4
Weight
Average: 331.9
Monoisotopic: 331.1161486
Chemical Formula
C19H22ClNS
InChI Key
XUPZAARQDNSRJB-SJDTYFKWSA-N
InChI
InChI=1S/C19H21NS.ClH/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;1H/b17-11+;
IUPAC Name
dimethyl({3-[(2E)-9-thiatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene]propyl})amine hydrochloride
SMILES
Cl.[H]\C(CCN(C)C)=C1\C2=CC=CC=C2CSC2=CC=CC=C12
ChemSpider
4938932
ChEBI
36805
ChEMBL
CHEMBL1711280
Wikipedia
Dosulepin
Predicted Properties
PropertyValueSource
Water Solubility0.000572 mg/mLALOGPS
logP4.98ALOGPS
logP4.52Chemaxon
logS-5.7ALOGPS
pKa (Strongest Basic)9.76Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area3.24 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity104.59 m3·mol-1Chemaxon
Polarizability34.14 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon