Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-13 11:55:24 UTC |
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Update Date | 2019-07-23 06:35:24 UTC |
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HMDB ID | HMDB0042038 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Tianeptine |
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Description | Tianeptine (INN) was discovered by The French Society of Medical Research in the 1960s. Under the trade-names (Stablon, Coaxil, Tatinol) it is a drug used for treating major depressive episodes (mild, moderate, or severe). It has structural similarities to the tricyclic antidepressants, but it has different pharmacological properties. Tianeptine is a selective serotonin reuptake enhancer (SSRE), opposite to the action of SSRIs. One review points to the cancellative effects of tianeptine and fluoxetine coadministration on serotonin reuptake. Another suggests that long-term administration of tianeptine has no effect on serotonin pathways. Tianeptine enhances the extracellular concentration of dopamine in the nucleus accumbens and modulates the D2 and D3 dopamine receptors, but this effect is modest and almost certainly indirect. There is also action on the NMDA and AMPA receptors. Recent reviews point to this pathway as a hypothesized mechanism of action, based on tianeptine's effect of reversing impaired neuroplasticity associated with stress. |
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Structure | |
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Synonyms | Value | Source |
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Stablon | Kegg | Ardix brand OF tianeptine, monosodium salt | HMDB | Tianeptine, (+-)-isomer | HMDB | Tianeptine, monosodium salt, (+-)-isomer | HMDB | (3-Chloro-6-methyl-5,5-dioxo-6,11-dihydrodibenzo(c,F)(1,2)thiazepin-11-yl)-7-aminoheptanoic acid | HMDB | Coaxil | HMDB | Tianeptine, monosodium salt | HMDB |
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Chemical Formula | C21H25ClN2O4S |
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Average Molecular Weight | 436.952 |
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Monoisotopic Molecular Weight | 436.122355695 |
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IUPAC Name | 7-({6-chloro-10-methyl-9,9-dioxo-9λ⁶-thia-10-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-2-yl}amino)heptanoic acid |
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Traditional Name | tianeptine |
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CAS Registry Number | 66981-73-5 |
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SMILES | CN1C2=CC=CC=C2C(NCCCCCCC(O)=O)C2=C(C=C(Cl)C=C2)S1(=O)=O |
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InChI Identifier | 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) |
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InChI Key | JICJBGPOMZQUBB-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Medium-chain fatty acids |
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Alternative Parents | |
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Substituents | - Medium-chain fatty acid
- Halogenated fatty acid
- Heterocyclic fatty acid
- Aralkylamine
- Aryl chloride
- Aryl halide
- Benzenoid
- Organosulfonic acid amide
- Organic sulfonic acid or derivatives
- Organosulfonic acid or derivatives
- Amino acid or derivatives
- Amino acid
- Carboxylic acid derivative
- Carboxylic acid
- Secondary aliphatic amine
- Monocarboxylic acid or derivatives
- Secondary amine
- Azacycle
- Organoheterocyclic compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic nitrogen compound
- Organohalogen compound
- Organochloride
- Organonitrogen compound
- Organooxygen compound
- Organopnictogen compound
- Carbonyl group
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0297-2955000000-f5d01fbffed94ca1d3d4 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0109-8938200000-3888305fcc28fb79c75d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kr-0102900000-b2120851dc0c11f1c49c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-056r-1139100000-82f01656084a2a95b7d9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0apl-9103000000-0ce94a818793b81c35d9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0002900000-a92759de6778d9d58e87 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-1107900000-7a69b9c7b39711b06f2a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9421000000-97f7c1339139f4d31260 | Spectrum |
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General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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