Structure via PubChem · Public domain (PubChem)
(±)-tianeptine
Sign in to saveAlso known as tianeptine, 7-[(3-chloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepin-11-yl)-amino]heptanoic acid S,S-dioxide
Tianeptine, sold under the brand names Stablon, Tatinol, and Coaxil among others, is an atypical tricyclic antidepressant which is used mainly in the treatment of major depressive disorder, although it may also be used to treat anxiety, asthma, and irritable bowel syndrome.
In the Vinony graph
Within Vinony's link graph, (±)-tianeptine is referenced by 1,402 other articles, and connects out to OPRM1, benzodiazepine drug and Russia.
Vinony files it under Anxiolytics, Chemical pages without DrugBank identifier and Chloroarenes.
Its subject is documented across 25 Wikipedia language editions.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 455249171
- Drug.IUPAC_name
- 7-[(3-Chloro-6-methyl-5,5-dioxo-11H-benzo[c][2,1]benzothiazepin-11-yl)amino]heptanoic acid
- Drug.image
- Tianeptine skeletal formula.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 225px
- Drug.image2
- Tianeptine_3D_ball-and-stick.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 200
- Drug.tradename
- Stablon, Coaxil, Tatinol
- Drug.legal_BR
- C1
- Drug.legal_status
- In general: Rx-onlyUS: Investigational New Drug AU: S4Others: controlled in FR, IT, BH, SG
- Drug.routes_of_administration
- By mouth
- Drug.bioavailability
- 99%
- Drug.protein_bound
- 95%
- Drug.metabolism
- Hepatic by β-oxidation
- Drug.elimination_half life
- 2.5–3 hours4–9 hours (elderly)
via Wikipedia infobox
Chemical data
- Formula
- C21H25ClN2O4S
- Molecular weight
- 437 g/mol
- IUPAC name
- 7-[(3-chloro-6-methyl-5,5-dioxo-11H-benzo[c][2,1]benzothiazepin-11-yl)amino]heptanoic acid
- SMILES
- CN1C2=CC=CC=C2C(C3=C(S1(=O)=O)C=C(C=C3)Cl)NCCCCCCC(=O)O
- InChIKey
- JICJBGPOMZQUBB-UHFFFAOYSA-N
- XLogP
- 1.2
- Polar surface area
- 95.1 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- bipolar disorder, nervous system disease, major depressive disorder
via ChEMBL · EBI
Research
684 papers- Antidepressants for the treatment of adults with major depressive disorder in the maintenance phase: a systematic review and network meta-analysis.Molecular psychiatry · 2023
- Classics in Chemical Neuroscience: Tianeptine.ACS chemical neuroscience · 2024
- Tianeptine, an atypical pharmacological approach to depression.Revista de psiquiatria y salud mental · 2019
- An Update on Tianeptine Regulations.Journal of addictions nursing · 2024
- Tianeptine Products: Public Health Threat or Niche Substance use?Journal of psychoactive drugs · 2025
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 436.122356
- Has use
- medication
Show 7 more facts
- chemical formula
- C₂₁H₂₅ClN₂O₄S
- World Health Organisation international non-proprietary name
- tianeptine
- canonical SMILES
- CN1C2=CC=CC=C2C(C3=C(S1(=O)=O)C=C(C=C3)Cl)NCCCCCCC(=O)O
- subject has role
- tricyclic antidepressant
- defined daily dose
- 37.5
- Commons category
- Tianeptine
via Wikidata · CC0
~23 min read
Encyclopedic overview
25 sectionsContents
- Medical uses
- Depression and anxiety
- Other uses
- Contraindications
- Side effects
- By frequency
- Pharmacology
- Pharmacodynamics
- Atypical μ-opioid receptor agonist
- Glutamatergic, neurotrophic, and neuroplastic modulation
- Serotonin reuptake enhancer
- Other actions
- Pharmacokinetics
- Chemistry
- Analogues
- History
- Society and culture
- Approval and brand names
- Development
- Recreational use
- Legality
- United States
- See also
- References
- External links
Tianeptine, sold under the brand names Stablon, Tatinol, and Coaxil among others, is an atypical tricyclic antidepressant which is used mainly in the treatment of major depressive disorder, although it may also be used to treat anxiety, asthma, and irritable bowel syndrome.
Tianeptine has antidepressant and anxiolytic effects with a relative lack of sedative, anticholinergic, and cardiovascular side effects. It has been found to act as an atypical agonist of the μ-opioid receptor with clinically negligible effects on the δ- and κ-opioid receptors. This may explain part of its antidepressant and anxiolytic effects; however, it is thought that tianeptine also modulates glutamate receptors, and this may also explain tianeptine's antidepressant/anxiolytic effects.
Excerpted from Wikipedia’s “(±)-tianeptine” article, available under the CC BY-SA 4.0 licence.