Tianeptine (BioDeep_00000017995)

human metabolite Chemicals and Drugs

代谢物信息卡片

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

化学式: C21H25ClN2O4S (436.12234800000004)
中文名称: 噻奈普汀
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CN1C2=CC=CC=C2C(C3=C(S1(=O)=O)C=C(C=C3)Cl)NCCCCCCC(=O)O
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)

描述信息

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 tianeptines effect of reversing impaired neuroplasticity associated with stress.
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents
C78272 - Agent Affecting Nervous System > C265 - Antidepressant Agent
C78272 - Agent Affecting Nervous System > C28197 - Antianxiety Agent
N - Nervous system > N06 - Psychoanaleptics > N06A - Antidepressants
Tianeptine is a selective facilitator of 5-HT uptake. Tianeptine has no affinity for a wide range of receptors, including 5-HT and dopamine (IC50>10 μM) and has no effect on noradrenalin or dopamine uptake. Tianeptine has antidepressant, anxiolytic, analgesic and neuroprotective activities[1][2][3][4].

同义名列表

9 个代谢物同义名

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; (3-Chloro-6-methyl-5,5-dioxo-6,11-dihydrodibenzo(c,F)(1,2)thiazepin-11-yl)-7-aminoheptanoic acid; Ardix brand OF tianeptine, monosodium salt; Tianeptine, monosodium salt, (+-)-isomer; Tianeptine, monosodium salt; Tianeptine, (+-)-isomer; Tianeptine; Stablon; Coaxil

数据库引用编号

16 个数据库交叉引用编号

ChEBI: CHEBI:190006
ChEBI: CHEBI:190008
ChEBI: CHEBI:91749
KEGG: C76315
PubChem: 68870
HMDB: HMDB0042038
DrugBank: DB09289
ChEMBL: CHEMBL1289110
Wikipedia: Tianeptine
chemspider: 62102
CAS: 191172-75-5
CAS: 169293-31-6
CAS: 72797-41-2
CAS: 66981-73-5
PMhub: MS000001581
medchemexpress: HY-90003

分类词条

Medium-chain fatty acids

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

9606 - Homo sapiens: -

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

文献列表

Burcu Ersoy, Marie-Louise Herzog, Wen Pan, Simone Schilling, Matthias Endres, Ria Göttert, Golo D Kronenberg, Karen Gertz. The atypical antidepressant tianeptine confers neuroprotection against oxygen-glucose deprivation. European archives of psychiatry and clinical neuroscience. 2023 Sep; ?(?):. doi: 10.1007/s00406-023-01685-9. [PMID: 37653354]
Fábio A Morais, Isabela S Lemos, Rafaela T Matiola, Maria Luísa S Freitas, Carolina G Alano, Julia Cabral, Leticia B Wessler, Jaqueline S Generoso, Giselli Scaini, Gislaine Z Réus, Emilio L Streck. Coadministration of tianeptine alters behavioral parameters and levels of neurotrophins in a chronic model of Maple Syrup Urine disease. Metabolic brain disease. 2022 06; 37(5):1585-1596. doi: 10.1007/s11011-022-00969-8. [PMID: 35394251]
Rahul Lauhan, Alan Hsu, Al Alam, Kristin Beizai. Tianeptine Abuse and Dependence: Case Report and Literature Review. Psychosomatics. 2018 11; 59(6):547-553. doi: 10.1016/j.psym.2018.07.006. [PMID: 30149933]
Małgorzata Szafarz, Agnieszka Wencel, Krzysztof Pociecha, Filip A Fedak, Piotr Wlaź, Elżbieta Wyska. Pharmacokinetic study of tianeptine and its active metabolite MC5 in rats following different routes of administration using a novel liquid chromatography tandem mass spectrometry analytical method. Naunyn-Schmiedeberg's archives of pharmacology. 2018 Feb; 391(2):185-196. doi: 10.1007/s00210-017-1448-2. [PMID: 29230490]
Sara K Dempsey, Justin L Poklis, Kacie Sweat, Kirk Cumpston, Carl E Wolf. Acute Toxicity From Intravenous Use of the Tricyclic Antidepressant Tianeptine. Journal of analytical toxicology. 2017 Jul; 41(6):547-550. doi: 10.1093/jat/bkx034. [PMID: 28541419]
Marta M Nowacka-Chmielewska, Daniela Kasprowska, Monika Paul-Samojedny, Anna M Bielecka-Wajdman, Jarosław J Barski, Andrzej Małecki, Ewa Obuchowicz. The effects of desipramine, fluoxetine, or tianeptine on changes in bulbar BDNF levels induced by chronic social instability stress and inflammation. Pharmacological reports : PR. 2017 Jun; 69(3):520-525. doi: 10.1016/j.pharep.2017.01.004. [PMID: 28359918]
Osama A Alkhamees, Abdulaziz S Al-Roujayee, Hatem M Abuohashish, Mohammed M Ahmed. Anti-osteoporotic effects of an antidepressant tianeptine on ovariectomized rats. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 Mar; 87(?):575-582. doi: 10.1016/j.biopha.2017.01.008. [PMID: 28081469]
Xu Deng, Yi-Jing Wu, Ying-Peng Chen, Hong-Hong Zheng, Zhong-Ping Wang, Yan Zhu, Xiu-Mei Gao, Yan-Tong Xu, Hong-Hua Wu. Nardonaphthalenones A and B from the roots and rhizomes of Nardostachys chinensis Batal. Bioorganic & medicinal chemistry letters. 2017 02; 27(4):875-879. doi: 10.1016/j.bmcl.2017.01.008. [PMID: 28094186]
Laia Tolosa, M José Gómez-Lechón, Nuria Jiménez, David Hervás, Ramiro Jover, M Teresa Donato. Advantageous use of HepaRG cells for the screening and mechanistic study of drug-induced steatosis. Toxicology and applied pharmacology. 2016 07; 302(?):1-9. doi: 10.1016/j.taap.2016.04.007. [PMID: 27089845]
Andrew C Kruegel, Madalee M Gassaway, Abhijeet Kapoor, András Váradi, Susruta Majumdar, Marta Filizola, Jonathan A Javitch, Dalibor Sames. Synthetic and Receptor Signaling Explorations of the Mitragyna Alkaloids: Mitragynine as an Atypical Molecular Framework for Opioid Receptor Modulators. Journal of the American Chemical Society. 2016 06; 138(21):6754-64. doi: 10.1021/jacs.6b00360. [PMID: 27192616]
Sevgi Türker-Kaya, Oğuz Mutlu, İpek K Çelikyurt, Furuzan Akar, Güner Ulak. Tianeptine, olanzapine and fluoxetine show similar restoring effects on stress induced molecular changes in mice brain: An FT-IR study. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2016 May; 161(?):178-85. doi: 10.1016/j.saa.2016.02.038. [PMID: 26952787]
Camille Bence, Alexandre Bonord, Camille Rebillard, Pascal Vaast, Charlotte Alexandre, Renaud Jardri, Benjamin Rolland. Neonatal Abstinence Syndrome Following Tianeptine Dependence During Pregnancy. Pediatrics. 2016 Jan; 137(1):. doi: 10.1542/peds.2015-1414. [PMID: 26659818]
Shuang Liang, Shu-Song Ying, Hong-Hua Wu, Yan-Ting Liu, Peng-Zhi Dong, Yan Zhu, Yan-Tong Xu. A novel sesquiterpene and three new phenolic compounds from the rhizomes of Acorus tatarinowii Schott. Bioorganic & medicinal chemistry letters. 2015 Oct; 25(19):4214-8. doi: 10.1016/j.bmcl.2015.08.001. [PMID: 26296476]
Renhua Zheng, Bo-Hyung Kim. Pharmacokinetic and bioequivalence assessment of two formulations of tianeptine sodium in healthy male volunteers. International journal of clinical pharmacology and therapeutics. 2014 Sep; 52(9):817-23. doi: 10.5414/cp202128. [PMID: 25109511]
Marta Benet, Marta Moya, M Teresa Donato, Agustín Lahoz, David Hervás, Carla Guzmán, M José Gómez-Lechón, José Vicente Castell, Ramiro Jover. A simple transcriptomic signature able to predict drug-induced hepatic steatosis. Archives of toxicology. 2014 Apr; 88(4):967-82. doi: 10.1007/s00204-014-1197-7. [PMID: 24469900]
C Chojnacki, E Walecka-Kapica, M Mokwinska, M Romanowski, M Pawlowicz, J Chojnacki, G Klupinska. Influence of tianeptine on melatonin homeostasis and psychosomatic symptoms in patients with irritable bowel syndrome. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society. 2013 Apr; 64(2):177-83. doi: NULL. [PMID: 23756392]
Oguz Mutlu, Esen Gumuslu, Guner Ulak, Ipek Komsuoglu Celikyurt, Sibel Kokturk, Hale Maral Kır, Furuzan Akar, Faruk Erden. Effects of fluoxetine, tianeptine and olanzapine on unpredictable chronic mild stress-induced depression-like behavior in mice. Life sciences. 2012 Dec; 91(25-26):1252-62. doi: 10.1016/j.lfs.2012.09.023. [PMID: 23069580]
Evi V Nagler, Angela C Webster, Raymond Vanholder, Carmine Zoccali. Antidepressants for depression in stage 3-5 chronic kidney disease: a systematic review of pharmacokinetics, efficacy and safety with recommendations by European Renal Best Practice (ERBP). Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2012 Oct; 27(10):3736-45. doi: 10.1093/ndt/gfs295. [PMID: 22859791]
Guilherme A Behr, José C F Moreira, Benicio N Frey. Preclinical and clinical evidence of antioxidant effects of antidepressant agents: implications for the pathophysiology of major depressive disorder. Oxidative medicine and cellular longevity. 2012; 2012(?):609421. doi: 10.1155/2012/609421. [PMID: 22693652]
Wei Liu, Xi-Ji Shu, Fu-Yin Chen, Cheng Zhu, Xiao-Hai Sun, Li-Jiang Liu, Yong-Xun Ai, Yu-Guang Li, Hu Zhao. Tianeptine reverses stress-induced asymmetrical hippocampal volume and N-acetylaspartate loss in rats: an in vivo study. Psychiatry research. 2011 Dec; 194(3):385-392. doi: 10.1016/j.pscychresns.2011.02.007. [PMID: 22047727]
Mohamed I Walash, Fathallah F Belal, Nahed M El-Enany, Heba Elmansi. Development and validation of stability indicating method for determination of sertraline following ICH guidlines and its determination in pharmaceuticals and biological fluids. Chemistry Central journal. 2011 Oct; 5(1):61. doi: 10.1186/1752-153x-5-61. [PMID: 21996025]
Alessandro Colasanti, Gabriel Esquivel, Erik den Boer, Annerieke Horlings, Abdul Dandachi, Jeff L Oostwegel, Eva L van Donkelaar, Eric J Griez, Koen Schruers. Effects of tryptophan depletion and tryptophan loading on the affective response to high-dose CO2 challenge in healthy volunteers. Psychopharmacology. 2011 Jun; 215(4):739-48. doi: 10.1007/s00213-011-2177-8. [PMID: 21336580]
Dorotea Mück-Seler, Marina Sagud, Alma Mihaljevi-Peles, Miro Jakovljevi, Nela Pivac. Baseline lipid levels and acute treatment response to paroxetine and tianeptine in depressed women. Journal of clinical psychopharmacology. 2011 Jun; 31(3):387-90. doi: 10.1097/jcp.0b013e318218f45f. [PMID: 21532370]
Torbjørn Breivik, Yngvar Gundersen, Per Gjermo, Inge Fristad, Per Kristian Opstad. Systemic chemical desensitization of peptidergic sensory neurons with resiniferatoxin inhibits experimental periodontitis. The open dentistry journal. 2011 Jan; 5(?):1-6. doi: 10.2174/1874210601105010001. [PMID: 21339860]
Fuad Lechin, Bertha van der Dijs, Betty Pardey-Maldonado, Jairo E Rivera, Scarlet Baez, Marcel E Lechin. Anorexia nervosa depends on adrenal sympathetic hyperactivity: opposite neuroautonomic profile of hyperinsulinism syndrome. Diabetes, metabolic syndrome and obesity : targets and therapy. 2010 Sep; 3(?):311-7. doi: 10.2147/dmsott.s10744. [PMID: 21437100]
Mustafa Ari, Süleyman Oktar, Mehmet Duru. Amitriptyline and tianeptine poisoning treated by naloxone. Human & experimental toxicology. 2010 Sep; 29(9):793-5. doi: 10.1177/0960327110372403. [PMID: 20498036]
Doaa Ahmed El-Setouhy, Nevine Shawky Abd El-Malak, Nevine Shawky Abd El-Malak. Formulation of a novel tianeptine sodium orodispersible film. AAPS PharmSciTech. 2010 Sep; 11(3):1018-25. doi: 10.1208/s12249-010-9464-2. [PMID: 20532710]
Samina Bano, Mehnaz Gitay, Iffat Ara, Abdulla Badawy. Acute effects of serotonergic antidepressants on tryptophan metabolism and corticosterone levels in rats. Pakistan journal of pharmaceutical sciences. 2010 Jul; 23(3):266-72. doi: . [PMID: 20566438]
Rosimary S Carvalho, Carolina M de Souza, Julliana C S Neves, Sergio A Holanda-Pinto, Lívia M S Pinto, Gerly A C Brito, Geanne M de Andrade. Effect of venlafaxine on bone loss associated with ligature-induced periodontitis in Wistar rats. Journal of negative results in biomedicine. 2010 Jun; 9(?):3. doi: 10.1186/1477-5751-9-3. [PMID: 20546603]
Britta Haenisch, Heinz Bönisch. Interaction of the human plasma membrane monoamine transporter (hPMAT) with antidepressants and antipsychotics. Naunyn-Schmiedeberg's archives of pharmacology. 2010 Jan; 381(1):33-9. doi: 10.1007/s00210-009-0479-8. [PMID: 20012264]
Fuad Lechin, Bertha van der Dijs, Betty Pardey-Maldonado, Jairo E Rivera, Marcel E Lechin, Scarlet Baez. Amantadine reduces glucagon and enhances insulin secretion throughout the oral glucose tolerance test: central plus peripheral nervous system mechanisms. Diabetes, metabolic syndrome and obesity : targets and therapy. 2009 Dec; 2(?):203-13. doi: 10.2147/dmsott.s7606. [PMID: 21437134]
Yanina Romero-Zerbo, Juan Decara, Rajaa el Bekay, Lourdes Sanchez-Salido, Ignacio Del Arco-Herrera, Fernando Rodríguez de Fonseca, Yolanda de Diego-Otero. Protective effects of melatonin against oxidative stress in Fmr1 knockout mice: a therapeutic research model for the fragile X syndrome. Journal of pineal research. 2009 Mar; 46(2):224-34. doi: 10.1111/j.1600-079x.2008.00653.x. [PMID: 19141086]
Verónica Trujillo, María Lujan Masseroni, Gloria Levin, Marta Magdalena Suárez. Tianeptine influence on plasmatic catecholamine levels and anxiety index in rats under variable chronic stress after early maternal separation. The International journal of neuroscience. 2009; 119(8):1210-27. doi: 10.1080/00207450802324713. [PMID: 19922351]
Zofia Rogóz, Grazyna Skuza, Monika Leśkiewicz, Bogusława Budziszewska. Effects of co-administration of fluoxetine or tianeptine with metyrapone on immobility time and plasma corticosterone concentration in rats subjected to the forced swim test. Pharmacological reports : PR. 2008 Nov; 60(6):880-8. doi: NULL. [PMID: 19211980]
Joanna Solich, Paulina Pałach, Bogusława Budziszewska, Marta Dziedzicka-Wasylewska. Effect of two behavioral tests on corticosterone level in plasma of mice lacking the noradrenaline transporter. Pharmacological reports : PR. 2008 Nov; 60(6):1008-13. doi: NULL. [PMID: 19211997]
I Tayfun Uzbay. Serotonergic anti-depressants and ethanol withdrawal syndrome: a review. Alcohol and alcoholism (Oxford, Oxfordshire). 2008 Jan; 43(1):15-24. doi: 10.1093/alcalc/agm145. [PMID: 17934195]
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S K Droste, M C Schweizer, S Ulbricht, J M H M Reul. Long-term voluntary exercise and the mouse hypothalamic-pituitary-adrenocortical axis: impact of concurrent treatment with the antidepressant drug tianeptine. Journal of neuroendocrinology. 2006 Dec; 18(12):915-25. doi: 10.1111/j.1365-2826.2006.01489.x. [PMID: 17076767]
Sevgi Tatar Ulu. Determination of tianeptine in human plasma using high-performance liquid chromatography with fluorescence detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 Apr; 834(1-2):62-7. doi: 10.1016/j.jchromb.2006.02.027. [PMID: 16520099]
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Torbjørn Breivik, Yngvar Gundersen, Harald Osmundsen, Frode Fonnum, Per Kristian Opstad. Neonatal dexamethasone and chronic tianeptine treatment inhibit ligature-induced periodontitis in adult rats. Journal of periodontal research. 2006 Feb; 41(1):23-32. doi: 10.1111/j.1600-0765.2005.00833.x. [PMID: 16409252]
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Nathalie Castanon, Chantal Médina, Cécile Mormède, Robert Dantzer. Chronic administration of tianeptine balances lipopolysaccharide-induced expression of cytokines in the spleen and hypothalamus of rats. Psychoneuroendocrinology. 2004 Jul; 29(6):778-90. doi: 10.1016/s0306-4530(03)00142-2. [PMID: 15110927]
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