8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 1H-indole-3-carboxylate (BioDeep_00000177358)

   

human metabolite blood metabolite


代谢物信息卡片


8-Methyl-8-azabicyclo[3.2.1]octan-3-yl 1H-indole-3-carboxylic acid

化学式: C17H20N2O2 (284.1525)
中文名称: 托烷司琼
谱图信息: 最多检出来源 Homo sapiens(not specific) 50%

分子结构信息

SMILES: CN1C2CCC1CC(C2)OC(=O)C1=CNC2=CC=CC=C12
InChI: InChI=1S/C17H20N2O2/c1-19-11-6-7-12(19)9-13(8-11)21-17(20)15-10-18-16-5-3-2-4-14(15)16/h2-5,10-13,18H,6-9H2,1H3

描述信息

D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D012702 - Serotonin Antagonists
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents
D005765 - Gastrointestinal Agents > D000932 - Antiemetics
D002491 - Central Nervous System Agents
Tropisetron (SDZ-ICS-930 free base) is a selective 5-HT3 receptor antagonist and α7-nicotinic receptor agonist with an IC50 of 70.1 ± 0.9 nM for 5-HT3 receptor. IC50 value: 70.1 ± 0.9 nM [1] Target: 5-HT3 receptor in vitro: Tropisetron specifically inhibited both IL-2 gene transcription and IL-2 synthesis in stimulated T cells. tropisetron inhibited both the binding to DNA and the transcriptional activity of NFAT and AP-1. We also observed that tropisetron is a potent inhibitor of PMA plus ionomycin-induced NF-(kappa)B activation but in contrast TNF(alpha)-mediated NF-(kappa)B activation was not affected by this antagonist [2]. Tropisetron prevents the phosphorylation and thus activation of the p38 MAPK, which is involved in post-transcriptional regulation of various cytokines [3]. in vivo: Two different doses of tropisetron (5 and 10 mg/kg) or vehicle were administered intraperitoneally 30 min before pMCAO. Neurological deficit scores, mortality rate and infarct volume were determined 24 h after permanent focal cerebral ischemia [4].

同义名列表

6 个代谢物同义名

8-Methyl-8-azabicyclo[3.2.1]octan-3-yl 1H-indole-3-carboxylic acid; 8-methyl-8-azabicyclo[3.2.1]octan-3-yl 1H-indole-3-carboxylate; 8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 1H-indole-3-carboxylate; Tropisetron; SDZ-ICS-930 (free base); Tropisetron



数据库引用编号

12 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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Plant Reactome(0)

INOH(0)

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1 个相关的物种来源信息

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

  • Shiva Gholizadeh-Ghaleh Aziz, Roya Naderi, Nima Mahmodian. Ameliorative effects of tropisetron on liver injury in streptozotocin-induced diabetic rats. Archives of physiology and biochemistry. 2021 Aug; 127(4):367-372. doi: 10.1080/13813455.2019.1640743. [PMID: 31306054]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Bagher Pourheydar, Mahrokh Samadi, Parisa Habibi, Ahmad Ali Nikibakhsh, Roya Naderi. Renoprotective effects of tropisetron through regulation of the TGF-β1, p53 and matrix metalloproteinases in streptozotocin-induced diabetic rats. Chemico-biological interactions. 2021 Feb; 335(?):109332. doi: 10.1016/j.cbi.2020.109332. [PMID: 33387473]
  • Mahrokh Samadi, Shiva Gholizadeh-Ghaleh Aziz, Roya Naderi. The effect of tropisetron on oxidative stress, SIRT1, FOXO3a, and claudin-1 in the renal tissue of STZ-induced diabetic rats. Cell stress & chaperones. 2021 01; 26(1):217-227. doi: 10.1007/s12192-020-01170-5. [PMID: 33047279]
  • Roya Naderi, Alireza Shirpoor, Mahrokh Samadi, Bagher Pourheydar, Azam Moslehi. Tropisetron attenuates pancreas apoptosis in the STZ-induced diabetic rats: involvement of SIRT1/NF-κB signaling. Pharmacological reports : PR. 2020 Dec; 72(6):1657-1665. doi: 10.1007/s43440-020-00146-7. [PMID: 32725585]
  • Ashkan Divanbeigi, Mohammad Nasehi, Salar Vaseghi, Sepideh Amiri, Mohammad-Reza Zarrindast. Tropisetron But Not Granisetron Ameliorates Spatial Memory Impairment Induced by Chronic Cerebral Hypoperfusion. Neurochemical research. 2020 Nov; 45(11):2631-2640. doi: 10.1007/s11064-020-03110-2. [PMID: 32797381]
  • Roya Naderi, Alireza Shirpoor, Mahrokh Samadi, Bagher Pourheydar, Azam Moslehi. Tropisetron improves pancreas function and increases insulin synthesis and secretion in the STZ-induced diabetic rats: involvement of UCP2/ZnT8 pathway. The Journal of pharmacy and pharmacology. 2020 Aug; 72(8):1082-1091. doi: 10.1111/jphp.13278. [PMID: 32349166]
  • Roya Naderi, Bagher Pourheydar, Rafigheh Ghiasi, Fardin Shafiei. Modulatory effect of tropisetron in the liver of streptozotocin-induced diabetes in rats: biochemical and histological evidence. Hormone molecular biology and clinical investigation. 2020 May; 41(3):. doi: 10.1515/hmbci-2020-0002. [PMID: 32364517]
  • Mohammad Amini, Ehsan Saboory, Bagher Pourheydar, Morteza Bagheri, Roya Naderi. Involvement of endocannabinoid system, inflammation and apoptosis in diabetes induced liver injury: Role of 5-HT3 receptor antagonist. International immunopharmacology. 2020 Feb; 79(?):106158. doi: 10.1016/j.intimp.2019.106158. [PMID: 31926479]
  • Bridget L Morse, Anil Kolur, Loyd R Hudson, Andrew T Hogan, Lisa Hong Chen, Ryan M Brackman, Geri A Sawada, John K Fallon, Philip C Smith, Kathleen M Hillgren. Pharmacokinetics of Organic Cation Transporter 1 (OCT1) Substrates in Oct1/2 Knockout Mice and Species Difference in Hepatic OCT1-Mediated Uptake. Drug metabolism and disposition: the biological fate of chemicals. 2020 02; 48(2):93-105. doi: 10.1124/dmd.119.088781. [PMID: 31771949]
  • Lucie Polovinkin, Ghérici Hassaine, Jonathan Perot, Emmanuelle Neumann, Anders A Jensen, Solène N Lefebvre, Pierre-Jean Corringer, Jacques Neyton, Christophe Chipot, Francois Dehez, Guy Schoehn, Hugues Nury. Conformational transitions of the serotonin 5-HT3 receptor. Nature. 2018 11; 563(7730):275-279. doi: 10.1038/s41586-018-0672-3. [PMID: 30401839]
  • Cunying Huang, Huihui Wan, Jing Zhang, Hongmin Zhong, Juan Li, YuMing Sun, Qing Wang, Hua Zhang. Quantification of ondansetron, granisetron and tropisetron in goat plasma using hydrophilic interaction liquid chromatography-solid phase extraction coupled with hydrophilic interaction liquid chromatography-triple quadrupole tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Sep; 1095(?):50-58. doi: 10.1016/j.jchromb.2018.07.009. [PMID: 30053687]
  • Reza Rahimian, Mohammad Reza Zirak, Mohammad Seyedabadi, Mojtaba Keshavarz, Amir Rashidian, Sareh Kazmi, Amir Hossein Jafarian, Gholamreza Karimi, Kazem Mousavizadeh. Protective effects of tropisetron on cerulein-induced acute pancreatitis in mice. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 Sep; 93(?):589-595. doi: 10.1016/j.biopha.2017.06.067. [PMID: 28686973]
  • Anita Barzegar-Fallah, Houman Alimoradi, Ali Razmi, Ahmad Reza Dehpour, Mojgan Asgari, Massoumeh Shafiei. Inhibition of calcineurin/NFAT pathway plays an essential role in renoprotective effect of tropisetron in early stage of diabetic nephropathy. European journal of pharmacology. 2015 Nov; 767(?):152-9. doi: 10.1016/j.ejphar.2015.10.019. [PMID: 26481166]
  • Anita Barzegar-Fallah, Houman Alimoradi, Firouzeh Asadi, Ahmad Reza Dehpour, Mojgan Asgari, Massoumeh Shafiei. Tropisetron ameliorates early diabetic nephropathy in streptozotocin-induced diabetic rats. Clinical and experimental pharmacology & physiology. 2015 Apr; 42(4):361-8. doi: 10.1111/1440-1681.12373. [PMID: 25676798]
  • Mohammad Reza Zirak, Reza Rahimian, Mahmoud Ghazi-Khansari, Ata Abbasi, Ali Razmi, Shahram Ejtemaei Mehr, Kazem Mousavizadeh, Ahmad Reza Dehpour. Tropisetron attenuates cisplatin-induced nephrotoxicity in mice. European journal of pharmacology. 2014 Sep; 738(?):222-9. doi: 10.1016/j.ejphar.2014.05.050. [PMID: 24905858]
  • Anita Barzegar-Fallah, Houman Alimoradi, Saeed Mehrzadi, Niloofar Barzegar-Fallah, Adib Zendedel, Ata Abbasi, Ahmad Reza Dehpour. The neuroprotective effect of tropisetron on vincristine-induced neurotoxicity. Neurotoxicology. 2014 Mar; 41(?):1-8. doi: 10.1016/j.neuro.2013.12.002. [PMID: 24374478]
  • Libo Li, Lei Xu, Jianshe Huang, Tianyan You. On-line focusing of 5-hydroxy-tryptamine type 3 receptor antagonists via the combination of field-enhanced sample injection and dynamic pH junction in capillary electrophoresis with amperometric detection. Journal of chromatography. A. 2014 Feb; 1331(?):117-22. doi: 10.1016/j.chroma.2014.01.028. [PMID: 24461640]
  • Q Yu, L Gao, M H Gu, M M Ma, Y K Liu, W Q Zu, J Zhang, W M Liang. Antiemetic effects of combined methylprednisolone and tropisetron in mastectomy. Minerva anestesiologica. 2013 Feb; 79(2):130-6. doi: NULL. [PMID: 23135693]
  • Houman Alimoradi, Anita Barzegar-Fallah, Gholamreza Hassanzadeh, Sanaz Mohammadi-Rick, Firouzeh Asadi, Bahram Delfan, Ata Abbasi, Ahmad Reza Dehpour. The cardioprotective effects of an antiemetic drug, tropisetron, on cardiomyopathy related to doxorubicin. Cardiovascular toxicology. 2012 Dec; 12(4):318-25. doi: 10.1007/s12012-012-9175-x. [PMID: 22744232]
  • M V Tzvetkov, A R Saadatmand, K Bokelmann, I Meineke, R Kaiser, J Brockmöller. Effects of OCT1 polymorphisms on the cellular uptake, plasma concentrations and efficacy of the 5-HT(3) antagonists tropisetron and ondansetron. The pharmacogenomics journal. 2012 Feb; 12(1):22-9. doi: 10.1038/tpj.2010.75. [PMID: 20921968]
  • Fu-Chao Liu, Huang-Ping Yu, Tsong-Long Hwang, Yung-Fong Tsai. Protective effect of tropisetron on rodent hepatic injury after trauma-hemorrhagic shock through P38 MAPK-dependent hemeoxygenase-1 expression. PloS one. 2012; 7(12):e53203. doi: 10.1371/journal.pone.0053203. [PMID: 23285267]
  • Daisuke Setoguchi, Masataka Nakamura, Henry Yatsuki, Eizo Watanabe, Yoshihisa Tateishi, Tomoyuki Kuwaki, Shigeto Oda. Experimental examination of anti-inflammatory effects of a 5-HT3 receptor antagonist, tropisetron, and concomitant effects on autonomic nervous function in a rat sepsis model. International immunopharmacology. 2011 Dec; 11(12):2073-8. doi: 10.1016/j.intimp.2011.08.022. [PMID: 21924384]
  • Synia Haub, Yvonne Ritze, Inga Ladel, Karolin Saum, Astrid Hubert, Astrid Spruss, Christian Trautwein, Stephan C Bischoff. Serotonin receptor type 3 antagonists improve obesity-associated fatty liver disease in mice. The Journal of pharmacology and experimental therapeutics. 2011 Dec; 339(3):790-8. doi: 10.1124/jpet.111.181834. [PMID: 21903748]
  • JianYe Yuan, JiYan Zhou, ZhiBi Hu, Guang Ji, JianQun Xie, DaZheng Wu. The effects of jatrorrhizine on contractile responses of rat ileum. European journal of pharmacology. 2011 Aug; 663(1-3):74-9. doi: 10.1016/j.ejphar.2011.05.002. [PMID: 21596029]
  • Oliver Bandschapp, Joerg Filitz, Albert Urwyler, Wolfgang Koppert, Wilhelm Ruppen. Tropisetron blocks analgesic action of acetaminophen: a human pain model study. Pain. 2011 Jun; 152(6):1304-1310. doi: 10.1016/j.pain.2011.02.003. [PMID: 21420788]
  • B S Cowie, K J Allen, S A Said, W J Inder. Anti-emetic doses of dexamethasone suppress cortisol response in laparoscopic cholecystectomy. Anaesthesia and intensive care. 2010 Jul; 38(4):667-70. doi: 10.1177/0310057x1003800408. [PMID: 20715729]
  • Synia Haub, Giridhar Kanuri, Valentina Volynets, Thomas Brune, Stephan C Bischoff, Ina Bergheim. Serotonin reuptake transporter (SERT) plays a critical role in the onset of fructose-induced hepatic steatosis in mice. American journal of physiology. Gastrointestinal and liver physiology. 2010 Mar; 298(3):G335-44. doi: 10.1152/ajpgi.00088.2009. [PMID: 19713474]
  • Katharina Heimes, Björn Feistel, Eugen J Verspohl. Impact of the 5-HT3 receptor channel system for insulin secretion and interaction of ginger extracts. European journal of pharmacology. 2009 Dec; 624(1-3):58-65. doi: 10.1016/j.ejphar.2009.09.049. [PMID: 19818348]
  • S Weber, V Volynets, G Kanuri, I Bergheim, S C Bischoff. Treatment with the 5-HT3 antagonist tropisetron modulates glucose-induced obesity in mice. International journal of obesity (2005). 2009 Dec; 33(12):1339-47. doi: 10.1038/ijo.2009.191. [PMID: 19823183]
  • Pan Deng, Dafang Zhong, Xiaoyan Chen. Determination of tropisetron in human plasma by liquid chromatography-tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2009 Apr; 49(3):848-52. doi: 10.1016/j.jpba.2008.12.038. [PMID: 19200686]
  • Liang-Wu Fu, Andrew Phan, John C Longhurst. Myocardial ischemia-mediated excitatory reflexes: a new function for thromboxane A2?. American journal of physiology. Heart and circulatory physiology. 2008 Dec; 295(6):H2530-40. doi: 10.1152/ajpheart.00790.2008. [PMID: 18952714]
  • Matthias F Seidel, Bernd L Fiebich, Gudrun Ulrich-Merzenich, Eduardo Candelario-Jalil, Franz-Walter Koch, Hans Vetter. Serotonin mediates PGE2 overexpression through 5-HT2A and 5-HT3 receptor subtypes in serum-free tissue culture of macrophage-like synovial cells. Rheumatology international. 2008 Aug; 28(10):1017-22. doi: 10.1007/s00296-008-0564-1. [PMID: 18368410]
  • Li Yu, Ludan Bao, Yunzhen Guo, Xingjie Guo. Determination of tropisetron in human plasma by high performance liquid chromatographic method with UV detection and its application to a bioequivalence study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 Feb; 846(1-2):20-3. doi: 10.1016/j.jchromb.2006.08.023. [PMID: 16962390]
  • E M Schneider, X Ma, T Stratz, W Müller, I Lorenz, W D Seeling. Immunomodulatory function of the 5-HT3 receptor antagonist tropisetron. Scandinavian journal of rheumatology. Supplement. 2004; 119(?):34-40. doi: NULL. [PMID: 15515411]
  • T Stratz, B Fiebich, U Haus, W Müller. Influence of tropisetron on the serum substance P levels in fibromyalgia patients. Scandinavian journal of rheumatology. Supplement. 2004; 119(?):41-3. doi: 10.1080/03009740410007023. [PMID: 15515412]
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  • T Stratz, W Müller. Treatment of systemic sclerosis with the 5-HT3 receptor antagonist tropisetron. Scandinavian journal of rheumatology. Supplement. 2004; 119(?):59-62. doi: 10.1080/03009740410007078. [PMID: 15515417]
  • Myo-Kyoung Kim, Joo-Youn Cho, Hyeong-Seok Lim, Kyoung-Seop Hong, Jae-Yong Chung, Kyun-Seop Bae, Dal-Seok Oh, Sang-Goo Shin, Sang-Hun Lee, Dong-Ho Lee, Bumchan Min, In-Jin Jang. Effect of the CYP2D6 genotype on the pharmacokinetics of tropisetron in healthy Korean subjects. European journal of clinical pharmacology. 2003 Jun; 59(2):111-6. doi: 10.1007/s00228-003-0595-1. [PMID: 12728290]
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