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Details

Stereochemistry ACHIRAL
Molecular Formula C19H21NS
Molecular Weight 295.442
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DOTHIEPIN, Z-

SMILES

CN(C)CC\C=C1\C2=C(CSC3=C1C=CC=C3)C=CC=C2

InChI

InChIKey=PHTUQLWOUWZIMZ-BOPFTXTBSA-N
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-

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8447840 | https://www.drugs.com/uk/dosulepin-capsules-25mg-leaflet.html | https://www.ncbi.nlm.nih.gov/pubmed/9408183

cis-Dosulepin is a stereoisomer of Dothiepin (trade name Prothiaden, Dothep, Thaden, and Dopress; Dosulepin (INN, BAN) a tricyclic antidepressant that is used in several European and South Asian countries, as well as Australia, South Africa, and New Zealand. Dosulepin is used for the treatment of the major depressive disorder and neuropathic pain. Dosulepin is only Therapeutic Goods Administration and Medicines and Healthcare products Regulatory Agency approved for the treatment of the major depressive disorder. Dothiepin is not used in the United States. The central action of cis-dosulepin was compared with that of its antidepressant stereoisomer trans-dosulepin, cis-dosulepin exerted weaker anti-reserpine, anti-tetrabenazine, and 3H-5-HT (serotonin) uptake inhibiting actions than trans-dosulepin, but cis-dosulepin's inhibition of 3H-dopamine and 3H-norepinephrine uptake was slightly more potent than that of trans-dosulepin. On the other hand, cis-dosulepin exhibited extremely potent anticholinergic action in oxotremorine induced tremor, isolated ileum and the 3H-quinuclidinyl benzilate binding test. It also showed potent apomorphine enhancing the action and shortened the period of immobility in the forced swimming test in animals.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.4 null [pKi]
18.0 nM [Kd]
109.0 nM [Kd]
38.0 nM [Kd]
61.0 nM [Kd]
92.0 nM [Kd]
8.6 nM [Kd]
46.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Prothiaden

Approved Use

Unknown
Primary
Prothiaden

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A comparative study of the therapeutic effect and cardiotoxicity of dothiepin HCl and doxepin HCl in reactive depression.
1981
[A case of choreoathetoid movements induced by anticholinergic drugs, trihexyphenidyl HCl and dosulepin HCl].
1992 Sep
Extreme suicidality following serotonin syndrome.
1995 Sep
Pharmacological profile of antidepressants and related compounds at human monoamine transporters.
1997 Dec 11
Antidepressant drugs and heart electrical field.
1998
Patents

Sample Use Guides

male Slc:Wistar rats: 40 mg/kg, PO
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
DOTHIEPIN, Z-
Common Name English
DOSULEPIN HYDROCHLORIDE IMPURITY E [EP IMPURITY]
Common Name English
CIS-DOTHIEPIN
Common Name English
DOSULEPIN, Z-ISOMER
Common Name English
1-Propanamine, 3-dibenzo[b,e]thiepin-11(6H)-ylidene-N,N-dimethyl-, (3Z)-
Systematic Name English
DOTHIEPIN, Z-ISOMER
Common Name English
(Z)-N,N-DIMETHYL-3-(6,11-DIHYDRODIBENZO(B,E)THIEPIN-11-YLIDENE)PROPYLAMINE
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID90873548
Created by admin on Sat Dec 16 09:33:27 GMT 2023 , Edited by admin on Sat Dec 16 09:33:27 GMT 2023
PRIMARY
CAS
25627-38-7
Created by admin on Sat Dec 16 09:33:27 GMT 2023 , Edited by admin on Sat Dec 16 09:33:27 GMT 2023
PRIMARY
FDA UNII
CZ377VWX9P
Created by admin on Sat Dec 16 09:33:27 GMT 2023 , Edited by admin on Sat Dec 16 09:33:27 GMT 2023
PRIMARY
PUBCHEM
5282426
Created by admin on Sat Dec 16 09:33:27 GMT 2023 , Edited by admin on Sat Dec 16 09:33:27 GMT 2023
PRIMARY