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
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+
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/2670509Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2670509
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
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P35367 Gene ID: 3269.0 Gene Symbol: HRH1 Target Organism: Homo sapiens (Human) |
8.4 null [pKi] | ||
18.0 nM [Kd] | |||
109.0 nM [Kd] | |||
38.0 nM [Kd] | |||
61.0 nM [Kd] | |||
92.0 nM [Kd] | |||
Target ID: CHEMBL228 Sources: https://www.drugbank.ca/drugs/DB09167 |
8.6 nM [Kd] | ||
Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9537821 |
46.0 nM [Kd] | ||
Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8447840 |
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Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8447840 |
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Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8447840 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Prothiaden Approved UseUnknown |
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Primary | Prothiaden Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9408183
male Slc:Wistar rats: 40 mg/kg, PO
Route of Administration:
Oral
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QN06AA16
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NCI_THESAURUS |
C28197
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WHO-ATC |
N06AA16
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36798
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DB09167
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D004308
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113-53-1
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DOSULEPIN
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951
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m4748
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7549
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1790
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204-031-2
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C72744
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W13O82Z7HL
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CHEMBL1492500
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3634
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5284550
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Dothiepin
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7181
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100000080788
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SUB06377MIG
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DTXSID2022961
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
METABOLITE ACTIVE (PARENT)
SALT/SOLVATE (PARENT)