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-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-
DescriptionCurator'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
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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
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 |
8.6 nM [Kd] | ||
Target ID: CHEMBL222 |
46.0 nM [Kd] | ||
Target ID: CHEMBL228 |
|||
Target ID: CHEMBL238 |
|||
Target ID: CHEMBL222 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Prothiaden Approved UseUnknown |
|||
| Primary | Prothiaden Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| Extreme suicidality following serotonin syndrome. | 1995 Sep |
|
| Antidepressant drugs and heart electrical field. | 1998 |
|
| Antidepressant induced cholestasis: hepatocellular redistribution of multidrug resistant protein (MRP2). | 2003 Feb |
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DTXSID90873548
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25627-38-7
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CZ377VWX9P
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5282426
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admin on Sat Dec 16 09:33:27 UTC 2023 , Edited by admin on Sat Dec 16 09:33:27 UTC 2023
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SUBSTANCE RECORD
