Sumatriptan (BioDeep_00000002002)

 

Secondary id: BioDeep_00000406027

human metabolite Chemicals and Drugs


代谢物信息卡片


1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulphonamide

化学式: C14H21N3O2S (295.13544060000004)
中文名称: 苏门曲普坦
谱图信息: 最多检出来源 Viridiplantae(plant) 83.33%

分子结构信息

SMILES: CNS(=O)(=O)CC1=CC2=C(C=C1)NC=C2CCN(C)C
InChI: InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3

描述信息

Oftentimes, serotonin levels in the brain become extremely erratic before the onset of a migraine. In an attempt to stabilize this, sumatriptan is administered to help aid in leveling the serotonin levels in the brain. Sumatriptan is structurally similar to serotonin, and is a 5-HT (5-HT1D) agonist, which is one of the receptors that serotonin binds to. The specific receptor subtype it activates is present in the cranial and basilar arteries. Activation of these receptors causes vasoconstriction of those dilated arteries. Sumatriptan is also shown to decrease the activity of the trigeminal nerve. Sumatriptan is a triptan drug including a sulfonamide group structurally similar to serotonin, and is a 5-HT (5-HT1D) agonist, which is one of the receptors that serotonin binds to. Oftentimes, serotonin levels in the brain become extremely erratic before the onset of a migraine. In an attempt to stabilize this, sumatriptan is administered to help aid in leveling the serotonin levels in the brain. A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of migraines. Sumatriptan (Imitrex, Imigran, Imigran Recovery) is a triptan drug including a sulfonamide group which was originally developed by Glaxo for the treatment of migraine headaches.
Oftentimes, serotonin levels in the brain become extremely erratic before the onset of a migraine. In an attempt to stabilize this, sumatriptan is administered to help aid in leveling the serotonin levels in the brain. Sumatriptan is structurally similar to serotonin, and is a 5-HT (5-HT1D) agonist, which is one of the receptors that serotonin binds to. The specific receptor subtype it activates is present in the cranial and basilar arteries. Activation of these receptors causes vasoconstriction of those dilated arteries. Sumatriptan is also shown to decrease the activity of the trigeminal nerve.; Sumatriptan is a triptan drug including a sulfonamide group structurally similar to serotonin, and is a 5-HT (5-HT1D) agonist, which is one of the receptors that serotonin binds to.
N - Nervous system > N02 - Analgesics > N02C - Antimigraine preparations > N02CC - Selective serotonin (5ht1) agonists
D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D017366 - Serotonin Receptor Agonists
C78272 - Agent Affecting Nervous System > C47794 - Serotonin Agonist
D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents
Sumatriptan (GR 43175) is an orally active 5-HT1 receptor agonist with IC50s of 7.3 nm, 9.3nm and 17.8 nm for 5-HT1D, 5-HT1B and 5-HT1F receptors, respectively. Sumatriptan can be used for migraine headache research[1][2][3][4].

同义名列表

22 个代谢物同义名

1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulphonamide; 1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide; 1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide; (3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulphonamide; (3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide; 3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulphonamide; 3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide; 3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulphonamide; 3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide; Glaxo wellcome brand OF sumatriptan; GSK Brand OF sumatriptan; Succinate, sumatriptan; Sumatriptan succinate; Sumatriptan GSK brand; Imigran recovery; Sumatriptanum; sumatriptan; Sumatran; Imigran; Imitrex; Sumax; GR 43175 free base



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

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

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

  • Ramesh Boinpally, Abhijeet Jakate, Matthew Butler, Antonia Periclou. Atogepant and sumatriptan: no clinically relevant drug-drug interactions in a randomized, open-label, crossover trial. Pain management. 2022 May; 12(4):499-508. doi: 10.2217/pmt-2021-0073. [PMID: 34898273]
  • Hasan Yousefi-Manesh, Samira Shirooie, Tayebeh Noori, Seyed Mohammad Tavangar, Mohammad Sheibani, Alireza Chaboki, Sina Mohammadi, Ahmad Reza Dehpour. Assessment of Sumatriptan on Sepsis-Induced Kidney injury in the Cecal Ligation and Puncture Mice Model. Drug research. 2022 Mar; 72(3):156-162. doi: 10.1055/a-1685-0482. [PMID: 34852366]
  • Rakesh Kumar Yadav, Kamal Shah, Hitesh Kumar Dewangan. Intranasal drug delivery of sumatriptan succinate-loaded polymeric solid lipid nanoparticles for brain targeting. Drug development and industrial pharmacy. 2022 Jan; 48(1):21-28. doi: 10.1080/03639045.2022.2090575. [PMID: 35703403]
  • Ibrahim Ethem Torun, Yasemin Baranoglu Kılınc, Erkan Kilinc. Endogenous and exogenous serotonin, but not sumatriptan, ameliorate seizures and neuroinflammation in the pentylenetetrazole-induced seizure model in rats. Arquivos de neuro-psiquiatria. 2022 01; 80(1):48-55. doi: 10.1590/0004-282x-anp-2021-0101. [PMID: 35239805]
  • Ahmad Reza Dehpour, Hasan Yousefi-Manesh, Mohammad Sheibani, Mohammad Amin Sadeghi, Sara Hemmati, Tayebeh Noori, Samira Shirooie. Evaluation of Anti-inflammatory and Antioxidant Effects of Sumatriptan on Carbon Tetrachloride-induced Hepatotoxicity in Rats. Drug research. 2022 Jan; 72(1):41-46. doi: 10.1055/a-1589-5395. [PMID: 34500479]
  • Olafur B Davidsson, Isa A Olofsson, Lisette Ja Kogelman, Michael Asger Andersen, Klaus Rostgaard, Henrik Hjalgrim, Jes Olesen, Thomas Folkmann Hansen. Twenty-five years of triptans - a nationwide population study. Cephalalgia : an international journal of headache. 2021 07; 41(8):894-904. doi: 10.1177/0333102421991809. [PMID: 33583217]
  • Mona H Abo Zaid, Samah Abo El Abass, Nahed El-Enany, Fatma Aly. Spectrofluorimetric investigation for determination of sumatriptan succinate: application to tablets and spiked human plasma. Luminescence : the journal of biological and chemical luminescence. 2021 May; 36(3):755-760. doi: 10.1002/bio.4000. [PMID: 33368986]
  • 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]
  • Bridget L Morse, John K Fallon, Anil Kolur, Andrew T Hogan, Philip C Smith, Kathleen M Hillgren. Comparison of Hepatic Transporter Tissue Expression in Rodents and Interspecies Hepatic OCT1 Activity. The AAPS journal. 2021 04; 23(3):58. doi: 10.1208/s12248-021-00583-z. [PMID: 33903987]
  • Moein Masjedi, Amir Azadi, Reza Heidari, Soliman Mohammadi-Samani. Nose-to-brain delivery of sumatriptan-loaded nanostructured lipid carriers: preparation, optimization, characterization and pharmacokinetic evaluation. The Journal of pharmacy and pharmacology. 2020 Oct; 72(10):1341-1351. doi: 10.1111/jphp.13316. [PMID: 32579251]
  • Fatemeh Gharishvandi, Alireza Abdollahi, Hamed Shafaroodi, Razieh Mohammad Jafari, Parvin Pasalar, Ahmad Reza Dehpour. Involvement of 5-HT1B/1D receptors in the inflammatory response and oxidative stress in intestinal ischemia/reperfusion in rats. European journal of pharmacology. 2020 Sep; 882(?):173265. doi: 10.1016/j.ejphar.2020.173265. [PMID: 32574671]
  • Abhijeet Jakate, Ramesh Boinpally, Matthew Butler, Kaifeng Lu, Danielle McGeeney, Antonia Periclou. Evaluation of the Pharmacokinetic Interaction of Ubrogepant Coadministered With Sumatriptan and of the Safety of Ubrogepant With Triptans. Headache. 2020 07; 60(7):1340-1350. doi: 10.1111/head.13862. [PMID: 32573795]
  • Pramod K Kalambate, Dhanjai, Ankita Sinha, Yankai Li, Yue Shen, Yunhui Huang. An electrochemical sensor for ifosfamide, acetaminophen, domperidone, and sumatriptan based on self-assembled MXene/MWCNT/chitosan nanocomposite thin film. Mikrochimica acta. 2020 06; 187(7):402. doi: 10.1007/s00604-020-04366-9. [PMID: 32572633]
  • Parnia Mobasheran, Nazanin Rajai, Parichehr Kohansal, Ahmad Reza Dehpour, Hamed Shafaroodi. The effects of acute sumatriptan treatment on renal ischemia/reperfusion injury in rat and the possible involvement of nitric oxide. Canadian journal of physiology and pharmacology. 2020 Apr; 98(4):252-258. doi: 10.1139/cjpp-2019-0301. [PMID: 31604019]
  • Li Guo, Muxin Gong, Sha Wu, Feng Qiu, Li Ma. Identification and quantification of the quality markers and anti-migraine active components in Chuanxiong Rhizoma and Cyperi Rhizoma herbal pair based on chemometric analysis between chemical constituents and pharmacological effects. Journal of ethnopharmacology. 2020 Jan; 246(?):112228. doi: 10.1016/j.jep.2019.112228. [PMID: 31513838]
  • Irene Wood, Lucas Fabian, Albertina Moglioni, Luis Fernando Cabeça, Eneida de Paula, Mónica Pickholz. Combining nuclear magnetic resonance with molecular dynamics simulations to address sumatriptan interaction with model membranes. Chemistry and physics of lipids. 2019 12; 225(?):104792. doi: 10.1016/j.chemphyslip.2019.104792. [PMID: 31361986]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Mohammad Sheibani, Hedyeh Faghir-Ghanesefat, Saman Dehpour, Hedieh Keshavarz-Bahaghighat, Mohammad Reza Sepand, Mohammad Hossein Ghahremani, Yaser Azizi, Nastaran Rahimi, Ahmad Reza Dehpour. Sumatriptan protects against myocardial ischaemia-reperfusion injury by inhibition of inflammation in rat model. Inflammopharmacology. 2019 Oct; 27(5):1071-1080. doi: 10.1007/s10787-019-00586-5. [PMID: 30929154]
  • Jan de Hoon, Anne Van Hecken, Corinne Vandermeulen, Marissa Herbots, Yumi Kubo, Ed Lee, Osa Eisele, Gabriel Vargas, Kristin Gabriel. Phase 1, randomized, parallel-group, double-blind, placebo-controlled trial to evaluate the effects of erenumab (AMG 334) and concomitant sumatriptan on blood pressure in healthy volunteers. Cephalalgia : an international journal of headache. 2019 01; 39(1):100-110. doi: 10.1177/0333102418776017. [PMID: 29783863]
  • Xiujuan Mi, Li Ran, Lixue Chen, Guangcheng Qin. Recurrent Headache Increases Blood-Brain Barrier Permeability and VEGF Expression in Rats. Pain physician. 2018 11; 21(6):E633-E642. doi: ". [PMID: 30508994]
  • Suresh Udutha, Gajji Shankar, Roshan M Borkar, Katragunta Kumar, G Srinivasulu, Lalitha Guntuku, V G M Naidu, Ragampeta Srinivas. Identification and characterization of stress degradation products of sumatriptan succinate by using LC/Q-TOF-ESI-MS/MS and NMR: Toxicity evaluation of degradation products. Journal of mass spectrometry : JMS. 2018 Oct; 53(10):963-975. doi: 10.1002/jms.4266. [PMID: 29987857]
  • Irene Wood, Juan M R Albano, Pedro L O Filho, Veronica Muniz Couto, Marcelo A de Farias, Rodrigo V Portugal, Eneida de Paula, Cristiano L P Oliveira, Monica Pickholz. A sumatriptan coarse-grained model to explore different environments: interplay with experimental techniques. European biophysics journal : EBJ. 2018 Jul; 47(5):561-571. doi: 10.1007/s00249-018-1278-2. [PMID: 29376196]
  • P Ronnander, L Simon, H Spilgies, A Koch, S Scherr. Dissolving polyvinylpyrrolidone-based microneedle systems for in-vitro delivery of sumatriptan succinate. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2018 Mar; 114(?):84-92. doi: 10.1016/j.ejps.2017.11.031. [PMID: 29203152]
  • Adriana E Bulboacă, Sorana D Bolboacă, Ioana C Stănescu, Carmen A Sfrângeu, Alina Porfire, Lucia Tefas, Angelo C Bulboacă. The effect of intravenous administration of liposomal curcumin in addition to sumatriptan treatment in an experimental migraine model in rats. International journal of nanomedicine. 2018; 13(?):3093-3103. doi: 10.2147/ijn.s162087. [PMID: 29872296]
  • Arindam Pal, Anirudh Gautam, Sagar Munjal. Pharmacokinetic Characterization and Dose Selection of a Novel Sumatriptan Nasal Spray Formulation, DFN-02. Journal of clinical pharmacology. 2017 Nov; 57(11):1472-1478. doi: 10.1002/jcph.946. [PMID: 28597922]
  • Caroline Machado Kopruszinski, Jennifer Yanhua Xie, Nathan Mackenzie Eyde, Bethany Remeniuk, Sarah Walter, Jennifer Stratton, Marcelo Bigal, Juliana Geremias Chichorro, David Dodick, Frank Porreca. Prevention of stress- or nitric oxide donor-induced medication overuse headache by a calcitonin gene-related peptide antibody in rodents. Cephalalgia : an international journal of headache. 2017 May; 37(6):560-570. doi: 10.1177/0333102416650702. [PMID: 27206958]
  • Maria-Jesus Blanco, Dana R Benesh, James A Knobelsdorf, Albert Khilevich, Guillermo S Cortez, Fese Mokube, Thomas D Aicher, Todd M Groendyke, Fredrik P Marmsater, Tony P Tang, Kirk W Johnson, Amy Clemens-Smith, Mark A Muhlhauser, Steven Swanson, John Catlow, Renee Emkey, Michael P Johnson, Jeffrey M Schkeryantz. Discovery of dual positive allosteric modulators (PAMs) of the metabotropic glutamate 2 receptor and CysLT1 antagonists for treating migraine headache. Bioorganic & medicinal chemistry letters. 2017 01; 27(2):323-328. doi: 10.1016/j.bmcl.2016.11.049. [PMID: 27908761]
  • S Hultzsch, C Schaefer. [Analgesic drugs during pregnancy]. Schmerz (Berlin, Germany). 2016 Dec; 30(6):583-593. doi: 10.1007/s00482-016-0167-9. [PMID: 27807736]
  • Sagar Munjal, Anirudh Gautam, Elliot Offman, Elimor Brand-Schieber, Kent Allenby, Dennis M Fisher. A Randomized Trial Comparing the Pharmacokinetics, Safety, and Tolerability of DFN-02, an Intranasal Sumatriptan Spray Containing a Permeation Enhancer, With Intranasal and Subcutaneous Sumatriptan in Healthy Adults. Headache. 2016 Oct; 56(9):1455-1465. doi: 10.1111/head.12905. [PMID: 27613076]
  • Dikla Gutman, Edward Hellriegel, Ernesto Aycardi, Marcelo E Bigal, Jeevan Kunta, Rohini Chitra, Sujay Kansagra, Orna Srur Kidron, Helena Knebel, Steven Linder, Yuju Ma, Mark Pierce, Paul K Winner, Ofer Spiegelstein. A Phase I, Open-Label, Single-Dose Safety, Pharmacokinetic, and Tolerability Study of the Sumatriptan Iontophoretic Transdermal System in Adolescent Migraine Patients. Headache. 2016 Sep; 56(8):1300-9. doi: 10.1111/head.12895. [PMID: 27474357]
  • Priti Girotra, Shailendra Kumar Singh. A Comparative Study of Orally Delivered PBCA and ApoE Coupled BSA Nanoparticles for Brain Targeting of Sumatriptan Succinate in Therapeutic Management of Migraine. Pharmaceutical research. 2016 07; 33(7):1682-95. doi: 10.1007/s11095-016-1910-8. [PMID: 27003706]
  • J Matthaei, D Kuron, F Faltraco, T Knoch, J N Dos Santos Pereira, M Abu Abed, T Prukop, J Brockmöller, M V Tzvetkov. OCT1 mediates hepatic uptake of sumatriptan and loss-of-function OCT1 polymorphisms affect sumatriptan pharmacokinetics. Clinical pharmacology and therapeutics. 2016 06; 99(6):633-41. doi: 10.1002/cpt.317. [PMID: 26659468]
  • Juliana Machado Brêtas, Isabela Costa César, Camila Machado Brêtas, Leonardo de Souza Teixeira, Karini Bruno Bellorio, Iram Moreira Mundim, Gerson Antônio Pianetti. Development and validation of an LC-ESI-MS/MS method for the simultaneous quantification of naproxen and sumatriptan in human plasma: application to a pharmacokinetic study. Analytical and bioanalytical chemistry. 2016 Jun; 408(15):3981-92. doi: 10.1007/s00216-016-9488-x. [PMID: 27020929]
  • Annelien De Pue, Bart Lutin, Koen Paemeleire. Chronic cluster headache and the pituitary gland. The journal of headache and pain. 2016; 17(?):23. doi: 10.1186/s10194-016-0614-0. [PMID: 26969187]
  • Girotra Priti Hansraj, Shailendra Kumar Singh, Pawan Kumar. Sumatriptan succinate loaded chitosan solid lipid nanoparticles for enhanced anti-migraine potential. International journal of biological macromolecules. 2015 Nov; 81(?):467-76. doi: 10.1016/j.ijbiomac.2015.08.035. [PMID: 26299709]
  • Erik Sjögren, David Dahlgren, Carl Roos, Hans Lennernäs. Human in vivo regional intestinal permeability: quantitation using site-specific drug absorption data. Molecular pharmaceutics. 2015 Jun; 12(6):2026-39. doi: 10.1021/mp500834v. [PMID: 25919764]
  • Ran D Goldman, Garth D Meckler. Intranasal sumatriptan for migraine in children. Canadian family physician Medecin de famille canadien. 2015 May; 61(5):435-7. doi: NULL. [PMID: 25971759]
  • Dan Wu, Ying-shu Quan, Fumio Kamiyama, Kosuke Kusamori, Hidemasa Katsumi, Toshiyasu Sakane, Akira Yamamoto. Improvement of transdermal delivery of sumatriptan succinate using a novel self-dissolving microneedle array fabricated from sodium hyaluronate in rats. Biological & pharmaceutical bulletin. 2015; 38(3):365-73. doi: 10.1248/bpb.b14-00502. [PMID: 25757917]
  • Jessica L Knittel, Shawn P Vorce, Barry Levine, Rhome L Hughes, Thomas Z Bosy. Multidrug toxicity involving sumatriptan. Journal of analytical toxicology. 2015 Jan; 39(1):75-9. doi: 10.1093/jat/bku120. [PMID: 25324526]
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