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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

SMILES

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

InChI

InChIKey=PHTUQLWOUWZIMZ-GZTJUZNOSA-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

Molecular Formula C19H21NS
Molecular Weight 295.442
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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 double-blind study of the efficacy and safety of dothiepin hydrochloride in the treatment of major depressive disorder.
1984 Nov
[Torsade de pointes caused by tricyclic antidepressive agents. Description of a clinical case].
1986 Dec
Dothiepin. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in depressive illness.
1989 Jul
[A case of choreoathetoid movements induced by anticholinergic drugs, trihexyphenidyl HCl and dosulepin HCl].
1992 Sep
Antagonism of the five cloned human muscarinic cholinergic receptors expressed in CHO-K1 cells by antidepressants and antihistaminics.
1993 Jun 9
Exacerbation of extrapyramidal symptoms with paroxetine.
1995 Sep
Extreme suicidality following serotonin syndrome.
1995 Sep
Nightmares and hallucinations after long-term intake of tramadol combined with antidepressants.
1996
Pharmacological profile of antidepressants and related compounds at human monoamine transporters.
1997 Dec 11
Antidepressant drugs and heart electrical field.
1998
Comparison of the effects of antidepressants and their metabolites on reuptake of biogenic amines and on receptor binding.
1999 Aug
Antidepressant induced cholestasis: hepatocellular redistribution of multidrug resistant protein (MRP2).
2003 Feb
Patents

Sample Use Guides

male Slc:Wistar rats: 40 mg/kg, PO
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:01:08 GMT 2023
Edited
by admin
on Fri Dec 15 16:01:08 GMT 2023
Record UNII
W13O82Z7HL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOTHIEPIN
MI  
Common Name English
DOSULEPIN
EP   HSDB   INN   WHO-DD  
INN  
Official Name English
DOTHIRPIN
Common Name English
DOTHIEPIN [MI]
Common Name English
DOSULEPIN [EP IMPURITY]
Common Name English
dosulepin [INN]
Common Name English
Dosulepin [WHO-DD]
Common Name English
1-PROPANAMINE, 3-DIBENZO(B,E)THIEPIN-11(6H)-YLIDENE-N,N-DIMETHYL
Common Name English
(E)-3-(DIBENZO(B,E)THIEPIN-11(6H)-YLIDENE)-N,N-DIMETHYLPROPAN-1-AMINE
Systematic Name English
DOSULEPIN [HSDB]
Common Name English
Classification Tree Code System Code
WHO-VATC QN06AA16
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
NCI_THESAURUS C28197
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
WHO-ATC N06AA16
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
Code System Code Type Description
CHEBI
36798
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
DRUG BANK
DB09167
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
MESH
D004308
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
CAS
113-53-1
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
WIKIPEDIA
DOSULEPIN
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
DRUG CENTRAL
951
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
MERCK INDEX
m4748
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY Merck Index
IUPHAR
7549
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
INN
1790
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-031-2
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
NCI_THESAURUS
C72744
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
FDA UNII
W13O82Z7HL
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
ChEMBL
CHEMBL1492500
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
RXCUI
3634
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY RxNorm
PUBCHEM
5284550
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
LACTMED
Dothiepin
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
HSDB
7181
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
SMS_ID
100000080788
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
EVMPD
SUB06377MIG
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
EPA CompTox
DTXSID2022961
Created by admin on Fri Dec 15 16:01:08 GMT 2023 , Edited by admin on Fri Dec 15 16:01:08 GMT 2023
PRIMARY
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