U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H21NS.ClH
Molecular Weight 331.903
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DOTHIEPIN HYDROCHLORIDE

SMILES

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

InChI

InChIKey=XUPZAARQDNSRJB-SJDTYFKWSA-N
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+;

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 8.4 null [pKi]
Antagonist
2778
 18.0 nM [Kd]
Antagonist
2778
 109.0 nM [Kd]
Antagonist
2778
 38.0 nM [Kd]
Antagonist
2778
 61.0 nM [Kd]
Antagonist
2778
 92.0 nM [Kd]
Inhibitor
8297
 8.6 nM [Kd]
Inhibitor
8297
 46.0 nM [Kd]
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Prothiaden

Approved Use

Unknown
Primary
Approved
8429
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
Exacerbation of extrapyramidal symptoms with paroxetine.
1995 Sep
Extreme suicidality following serotonin syndrome.
1995 Sep
Pharmacological profile of antidepressants and related compounds at human monoamine transporters.
1997 Dec 11
Patents

Patents

JP2011504928A
8
JP2011526251A
112
WO2007136743
3

Sample Use Guides

In Vivo Use Guide
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 15:10:28 UTC 2023
Edited
by admin
on Fri Dec 15 15:10:28 UTC 2023
Record UNII
3H0042311V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOTHIEPIN HYDROCHLORIDE
MI   USAN  
USAN  
Official Name English
DOSULEPIN HYDROCHLORIDE [MART.]
Common Name English
1-PROPANAMINE, 3-DIBENZO(B,E)THIEPIN-11(6H)-YLIDENE-N,N-DIMETHYL-, HYDROCHLORIDE
Systematic Name English
THADEN
Brand Name English
DOTHIEPIN HCL
Common Name English
Dosulepin hydrochloride [WHO-DD]
Common Name English
PROTHIADEN
Brand Name English
DOPRESS
Brand Name English
DOSULEPIN HYDROCHLORIDE [JAN]
Common Name English
DOTHIEPIN HYDROCHLORIDE [USAN]
Common Name English
(E)-3-(DIBENZO(B,E)THIEPIN-11(6H)-YLIDENE)-N,N-DIMETHYLPROPAN-1-AMINE HYDROCHLORIDE
Systematic Name English
DOSULEPIN HYDROCHLORIDE
EP   JAN   MART.   WHO-DD  
Common Name English
NSC-172130
Code English
DOTHEP
Brand Name English
DOSULEPIN HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
DOTHIEPIN HYDROCHLORIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Fri Dec 15 15:10:28 UTC 2023 , Edited by admin on Fri Dec 15 15:10:28 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID7047778
Created by admin on Fri Dec 15 15:10:28 UTC 2023 , Edited by admin on Fri Dec 15 15:10:28 UTC 2023
PRIMARY
RXCUI
142133
Created by admin on Fri Dec 15 15:10:28 UTC 2023 , Edited by admin on Fri Dec 15 15:10:28 UTC 2023
PRIMARY RxNorm
EVMPD
SUB01821MIG
Created by admin on Fri Dec 15 15:10:28 UTC 2023 , Edited by admin on Fri Dec 15 15:10:28 UTC 2023
PRIMARY
ChEMBL
CHEMBL1492500
Created by admin on Fri Dec 15 15:10:28 UTC 2023 , Edited by admin on Fri Dec 15 15:10:28 UTC 2023
PRIMARY
FDA UNII
3H0042311V
Created by admin on Fri Dec 15 15:10:28 UTC 2023 , Edited by admin on Fri Dec 15 15:10:28 UTC 2023
PRIMARY
NCI_THESAURUS
C78018
Created by admin on Fri Dec 15 15:10:28 UTC 2023 , Edited by admin on Fri Dec 15 15:10:28 UTC 2023
PRIMARY
ECHA (EC/EINECS)
212-978-8
Created by admin on Fri Dec 15 15:10:28 UTC 2023 , Edited by admin on Fri Dec 15 15:10:28 UTC 2023
PRIMARY
DRUG BANK
DBSALT001822
Created by admin on Fri Dec 15 15:10:28 UTC 2023 , Edited by admin on Fri Dec 15 15:10:28 UTC 2023
PRIMARY
SMS_ID
100000091934
Created by admin on Fri Dec 15 15:10:28 UTC 2023 , Edited by admin on Fri Dec 15 15:10:28 UTC 2023
PRIMARY
PUBCHEM
6433931
Created by admin on Fri Dec 15 15:10:28 UTC 2023 , Edited by admin on Fri Dec 15 15:10:28 UTC 2023
PRIMARY
MERCK INDEX
m4748
Created by admin on Fri Dec 15 15:10:28 UTC 2023 , Edited by admin on Fri Dec 15 15:10:28 UTC 2023
PRIMARY Merck Index
CHEBI
31519
Created by admin on Fri Dec 15 15:10:28 UTC 2023 , Edited by admin on Fri Dec 15 15:10:28 UTC 2023
PRIMARY
NSC
172130
Created by admin on Fri Dec 15 15:10:28 UTC 2023 , Edited by admin on Fri Dec 15 15:10:28 UTC 2023
PRIMARY
CAS
897-15-4
Created by admin on Fri Dec 15 15:10:28 UTC 2023 , Edited by admin on Fri Dec 15 15:10:28 UTC 2023
PRIMARY
Related Record Type Details
Structure of DOTHIEPIN
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of DOTHIEPIN SULFOXIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of (E)-11-[3-(dimethylamino)propylidene]-6,11-dihydro-5H-5λ6-dibenzo[b,e]thiepin-5,5-dione,
IMPURITY -> PARENT
Structure of (11RS)-11-[3-(dimethylamino)propyl]-6,11-dihydrodibenzo[b,e]thiepin-11-ol
IMPURITY -> PARENT
Structure of DOTHIEPIN, Z-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of DIBENZO(B,E)THIEPIN-11(6H)-ONE
IMPURITY -> PARENT
Related Record Type Details
Structure of DOTHIEPIN
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966