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Tianeptine
Tianeptine
Synonyms None
Brand names Coaxil, Stablon
IUPAC name

IUPAC name
7-[(3-Chloro-6-methyl-5,5-dioxido-6,11-dihydrodibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic acid
ChemSpider

62102

DrugBank

None

PubChem

68870

PDB fields

N/A

Formula

C21H25ClN2O4S

InChI
InChI
1S/C21H25ClN2O4S/c1-24-18-9-6-5-8-16(18)21(23-13-7-3-2-4-10-20(25)26)17-12-11-15(22)14-19(17)29(24,27)28/h5-6,8-9,11-12,14,21,23H,2-4,7,10,13H2,1H3,(H,25,26)
InChIKey
InChIKey
JICJBGPOMZQUBB-UHFFFAOYSA-N
SMILES
SMILES
CN1C2=CC=CC=C2C(C3=C(S1(=O)=O)C=C(C=C3)Cl)NCCCCCCC(=O)O
(Jmol 3D structure)
Mol. mass

436.9522 g/mol

Tianeptine is a tricyclic antidepressant that instead of inhibiting the reuptake of serotonin and/or noradrenaline it is believed to act by enhancing the reuptake of serotonin, along with additional effects on glutamate-mediated neurotransmission.[1] It is also used to treat asthma and irritable bowel syndrome.[2][3][4] Its anticholinergic, cardiovascular and antihistamine effects are believed to be virtually non-existent, as is its toxicity in overdose and it is considered to be a second-generation antidepressant.[5]

External linksEdit

Reference listEdit

  1. McEwen, BS; Chattarji, S; Diamond, DM; Jay, TM; Reagan, LP; Svenningsson, P; Fuchs, E (March 2010). "The neurobiological properties of tianeptine (Stablon): from monoamine hypothesis to glutamatergic modulation.". Molecular Psychiatry 15 (3): 237–49. PMC 2902200. PMID 19704408. doi:10.1038/mp.2009.80. 
  2. Brayfield, A, ed. (13 December 2013). "Tianeptine Sodium". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 16 August 2014. 
  3. Sohn, W; Lee, OY; Kwon, JG; Park, KS; Lim, YJ; Kim, TH; Jung, SW; Kim, JI (September 2012). "Tianeptine vs amitriptyline for the treatment of irritable bowel syndrome with diarrhea: a multicenter, open-label, non-inferiority, randomized controlled study.". Neurogastroenterology and Motility 24 (9): 860–e398. PMID 22679908. doi:10.1111/j.1365-2982.2012.01945.x. 
  4. Chojnacki, C; Walecka-Kapica, E; Mokwinska, M; Romanowski, M; Pawlowicz, M; Chojnacki, J; Klupinska, G (April 2013). "Influence of tianeptine on melatonin homeostasis and psychosomatic symptoms in patients with irritable bowel syndrome." (PDF). Journal of Physiology and Pharmacology 64 (2): 177–83. PMID 23756392. 
  5. Wilde, MI; Benfield, P (March 1995). "Tianeptine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in depression and coexisting anxiety and depression.". Drugs 49 (3): 411–39. PMID 7774514. doi:10.2165/00003495-199549030-00007. 

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