Retigabine (BioDeep_00000009606)
Secondary id: BioDeep_00001871298
human metabolite blood metabolite
代谢物信息卡片
Ethyl N-(2-amino-4-(4-fluorobenzylamino)phenyl)carbamate hydrochloride
化学式: C16H18FN3O2 (303.1383)
中文名称: 瑞替加滨
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCOC(=O)NC1=C(C=C(C=C1)NCC2=CC=C(C=C2)F)N
InChI: InChI=1S/C16H18FN3O2/c1-2-22-16(21)20-15-8-7-13(9-14(15)18)19-10-11-3-5-12(17)6-4-11/h3-9,19H,2,10,18H2,1H3,(H,20,21)
描述信息
C78272 - Agent Affecting Nervous System > C264 - Anticonvulsant Agent
D002491 - Central Nervous System Agents > D000927 - Anticonvulsants
N - Nervous system > N03 - Antiepileptics > N03A - Antiepileptics
D049990 - Membrane Transport Modulators
Same as: D09569
同义名列表
15 个代谢物同义名
Ethyl N-(2-amino-4-(4-fluorobenzylamino)phenyl)carbamate hydrochloride; N-(2-Amino-4-(4-fluorobenzylamino)-phenyl) carbamic acid ethyl ester; ethyl N-(2-amino-4-{[(4-fluorophenyl)methyl]amino}phenyl)carbamate; N-(2-Amino-4-(4-fluorobenzylamino)phenyl)carbamic acid ethyl ester; N-(2-Amino-4-(4-fluorobenzylamino)-phenyl) carbamate ethyl ester; N-(2-Amino-4-(4-fluorobenzylamino)phenyl)carbamate ethyl ester; Ethyl {2-amino-4-[(4-fluorobenzyl)amino]phenyl}carbamic acid; Ethyl {2-amino-4-[(4-fluorobenzyl)amino]phenyl}carbamate; Ethyl 2-amino-4-((p-fluorobenzyl)amino)carbanilic acid; Ethyl 2-amino-4-((p-fluorobenzyl)amino)carbanilate; Retigabine; Ezogabine; D-23129; Potiga; Retigabine
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:68584
- KEGG: C13826
- PubChem: 121892
- HMDB: HMDB0257171
- Metlin: METLIN69720
- DrugBank: DB04953
- ChEMBL: CHEMBL41355
- Wikipedia: Ezogabine
- chemspider: 108740
- CAS: 150812-12-7
- PMhub: MS000023406
- PubChem: 854071
- PDB-CCD: FBX
- NIKKAJI: J751.646K
- KNApSAcK: 68584
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
- Michael Pökl, Akshay Sridhar, Damon J A Frampton, Veronika A Linhart, Lucie Delemotte, Sara I Liin. Subtype-specific modulation of human KV 7 channels by the anticonvulsant cannabidiol through a lipid-exposed pore-domain site.
British journal of pharmacology.
2023 12; 180(23):2956-2972. doi:
10.1111/bph.16183. [PMID: 37377025] - Petra Bloms-Funke, Marion Bankstahl, Jens Bankstahl, Christa Kneip, Wolfgang Schröder, Wolfgang Löscher. The novel dual-mechanism Kv7 potassium channel/TSPO receptor activator GRT-X is more effective than the Kv7 channel opener retigabine in the 6-Hz refractory seizure mouse model.
Neuropharmacology.
2022 02; 203(?):108884. doi:
10.1016/j.neuropharm.2021.108884. [PMID: 34785163] - Xu Chen, Yuhong Zhang, Xiang Ren, Qi Su, Yan Liu, Xing Dang, Yuanyuan Qin, Xinyi Yang, Zhengcao Xing, Yajie Shen, Yaya Wang, Zhantao Bai, Edward T H Yeh, Hongmei Wu, Yitao Qi. The SUMO-specific protease SENP2 plays an essential role in the regulation of Kv7.2 and Kv7.3 potassium channels.
The Journal of biological chemistry.
2021 10; 297(4):101183. doi:
10.1016/j.jbc.2021.101183. [PMID: 34509475] - Aya M Mostafa, Azza H Rageh, Marwa F B Ali, Fardous A Mohamed. Micelle and inclusion complex enhanced spectrofluorimetric methods for determination of Retigabine: Application in pharmaceutical and biological analysis.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.
2019 Jan; 207(?):251-261. doi:
10.1016/j.saa.2018.09.030. [PMID: 30248612] - Rían W Manville, Geoffrey W Abbott. Ancient and modern anticonvulsants act synergistically in a KCNQ potassium channel binding pocket.
Nature communications.
2018 09; 9(1):3845. doi:
10.1038/s41467-018-06339-2. [PMID: 30242262] - Valentina Franco, Katia Baruffi, Giuliana Gatti, Roberto Marchiselli, Cinzia Fattore, Maria Paola Canevini, Francesca Crema, Emilio Perucca. A simple and rapid HPLC-UV method for the determination of retigabine in human plasma.
Biomedical chromatography : BMC.
2018 May; 32(5):e4168. doi:
10.1002/bmc.4168. [PMID: 29235121] - Keaton S Smetana, Aaron M Cook, Melissa L Thompson Bastin, Douglas R Oyler. Antiepileptic dosing for critically ill adult patients receiving renal replacement therapy.
Journal of critical care.
2016 12; 36(?):116-124. doi:
10.1016/j.jcrc.2016.06.023. [PMID: 27546759] - Bo-Chuan Teng, Yan Song, Fan Zhang, Tian-Yang Ma, Jin-Long Qi, Hai-Lin Zhang, Gang Li, KeWei Wang. Activation of neuronal Kv7/KCNQ/M-channels by the opener QO58-lysine and its anti-nociceptive effects on inflammatory pain in rodents.
Acta pharmacologica Sinica.
2016 Aug; 37(8):1054-62. doi:
10.1038/aps.2016.33. [PMID: 27264315] - Lindsay Brown, Samuel Gutherz, Catherine Kulick, Colin Soper, Alexei Kondratyev, Patrick A Forcelli. Profile of retigabine-induced neuronal apoptosis in the developing rat brain.
Epilepsia.
2016 Apr; 57(4):660-70. doi:
10.1111/epi.13335. [PMID: 26865186] - Jin-Long Li, Zhao-Bing Gao, Wei-Min Zhao. Identification and Evaluation of Antiepileptic Activity of C21 Steroidal Glycosides from the Roots of Cynanchum wilfordii.
Journal of natural products.
2016 Jan; 79(1):89-97. doi:
10.1021/acs.jnatprod.5b00766. [PMID: 26716755] - Juanjuan Wang, Yuan Li, Zhiyan Hui, Min Cao, Ruiming Shi, Wei Zhang, Limeng Geng, Xihui Zhou. Functional analysis of potassium channels in Kv7.2 G271V mutant causing early onset familial epilepsy.
Brain research.
2015 Aug; 1616(?):112-22. doi:
10.1016/j.brainres.2015.04.060. [PMID: 25960349] - Marco Treven, Xaver Koenig, Elham Assadpour, Enkhbileg Gantumur, Christiane Meyer, Karlheinz Hilber, Stefan Boehm, Helmut Kubista. The anticonvulsant retigabine is a subtype selective modulator of GABAA receptors.
Epilepsia.
2015 Apr; 56(4):647-57. doi:
10.1111/epi.12950. [PMID: 25779225] - Raghavender Pottabathini, Anil Kumar, Archana Bhatnagar, Sukant Garg. Possible involvement of nitric oxide modulatory mechanism in the protective effect of retigabine against spinal nerve ligation-induced neuropathic pain.
Cellular and molecular neurobiology.
2015 Jan; 35(1):137-46. doi:
10.1007/s10571-014-0105-2. [PMID: 25182225] - Pingzheng Zhou, Yangming Zhang, Haiyan Xu, Fei Chen, Xueqin Chen, Xiaoying Li, Xiaoping Pi, Lipeng Wang, Li Zhan, Fajun Nan, Zhaobing Gao. P-retigabine: an N-propargyled retigabine with improved brain distribution and enhanced antiepileptic activity.
Molecular pharmacology.
2015 Jan; 87(1):31-8. doi:
10.1124/mol.114.095190. [PMID: 25319542] - Debra J Tompson, Mauro Buraglio, Jonathan Bullman, Christopher S Crean, Kirsty Rayner. Effect of hemodialysis on pharmacokinetics of ezogabine/retigabine and its N-acetyl metabolite in patients with end stage renal disease.
Current clinical pharmacology.
2014; 9(4):319-25. doi:
10.2174/157488470904141105142635. [PMID: 25387761] - Christopher S Crean, Debra J Tompson, Mauro Buraglio. The effect of ezogabine on the pharmacokinetics of an oral contraceptive agent.
International journal of clinical pharmacology and therapeutics.
2013 Nov; 51(11):847-53. doi:
10.5414/cp201916. [PMID: 24040852] - Debra J Tompson, Christopher S Crean. Clinical pharmacokinetics of retigabine/ezogabine.
Current clinical pharmacology.
2013 Nov; 8(4):319-31. doi:
10.2174/15748847113089990053. [PMID: 23342983] - Abhilasha Verma, Rajnish Kumar, Manoj Kumar. Ezogabine: development and role in the management of epileptic seizures.
Mini reviews in medicinal chemistry.
2013 Apr; 13(5):697-705. doi:
10.2174/1389557511313050006. [PMID: 22931529] - Neil Brickel, Paul Gandhi, Kevan VanLandingham, Janet Hammond, Sarah DeRossett. The urinary safety profile and secondary renal effects of retigabine (ezogabine): a first-in-class antiepileptic drug that targets KCNQ (K(v)7) potassium channels.
Epilepsia.
2012 Apr; 53(4):606-12. doi:
10.1111/j.1528-1167.2012.03441.x. [PMID: 22428574] - . Retigabine: fewer drug interactions.
Prescrire international.
2012 Mar; 21(125):61. doi:
. [PMID: 22428181] - Cinzia Fattore, Emilio Perucca. Novel medications for epilepsy.
Drugs.
2011 Nov; 71(16):2151-78. doi:
10.2165/11594640-000000000-00000. [PMID: 22035515] - Svein I Johannessen, Cecilie Johannessen Landmark. Antiepileptic drug interactions - principles and clinical implications.
Current neuropharmacology.
2010 Sep; 8(3):254-67. doi:
10.2174/157015910792246254. [PMID: 21358975] - Jared W Young, Andrew K L Goey, Arpi Minassian, William Perry, Martin P Paulus, Mark A Geyer. GBR 12909 administration as a mouse model of bipolar disorder mania: mimicking quantitative assessment of manic behavior.
Psychopharmacology.
2010 Feb; 208(3):443-54. doi:
10.1007/s00213-009-1744-8. [PMID: 20020109] - Jarogniew J Luszczki, Jim Z Wu, Grzegorz Raszewski, Stanislaw J Czuczwar. Isobolographic characterization of interactions of retigabine with carbamazepine, lamotrigine, and valproate in the mouse maximal electroshock-induced seizure model.
Naunyn-Schmiedeberg's archives of pharmacology.
2009 Feb; 379(2):163-79. doi:
10.1007/s00210-008-0349-9. [PMID: 18773196] - Wei Bu, Mai Nguyen, Christine Xu, Chin-Chung Lin, Li-Tain Yeh, Virginia Borges. Determination of N-acetyl retigabine in dog plasma by LC/MS/MS following off-line microElution 96-well solid phase extraction.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2007 Jun; 852(1-2):465-72. doi:
10.1016/j.jchromb.2007.02.019. [PMID: 17350902] - Mark A Punke, Patrick Friederich. Amitriptyline is a potent blocker of human Kv1.1 and Kv7.2/7.3 channels.
Anesthesia and analgesia.
2007 May; 104(5):1256-64, tables of contents. doi:
10.1213/01.ane.0000260310.63117.a2. [PMID: 17456683] - Francesca Boscia, Lucio Annunziato, Maurizio Taglialatela. Retigabine and flupirtine exert neuroprotective actions in organotypic hippocampal cultures.
Neuropharmacology.
2006 Aug; 51(2):283-94. doi:
10.1016/j.neuropharm.2006.03.024. [PMID: 16697426] - Jürgen Borlak, Antje Gasparic, Mathias Locher, Hubert Schupke, Robert Hermann. N-Glucuronidation of the antiepileptic drug retigabine: results from studies with human volunteers, heterologously expressed human UGTs, human liver, kidney, and liver microsomal membranes of Crigler-Najjar type II.
Metabolism: clinical and experimental.
2006 Jun; 55(6):711-21. doi:
10.1016/j.metabol.2006.01.006. [PMID: 16713428] - R Hermann, J Borlak, U Munzel, G Niebch, U Fuhr, J Maus, K Erb. The role of Gilbert's syndrome and frequent NAT2 slow acetylation polymorphisms in the pharmacokinetics of retigabine.
The pharmacogenomics journal.
2006 May; 6(3):211-9. doi:
10.1038/sj.tpj.6500359. [PMID: 16402080] - Yong-Jin Wu, Christopher G Boissard, Jie Chen, William Fitzpatrick, Qi Gao, Valentin K Gribkoff, David G Harden, Huan He, Ronald J Knox, Joanne Natale, Rick L Pieschl, John E Starrett, Li-Qiang Sun, Mark Thompson, David Weaver, Dedong Wu, Steven I Dworetzky. (S)-N-[1-(4-cyclopropylmethyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-ethyl]-3-(2-fluoro-phenyl)-acrylamide is a potent and efficacious KCNQ2 opener which inhibits induced hyperexcitability of rat hippocampal neurons.
Bioorganic & medicinal chemistry letters.
2004 Apr; 14(8):1991-5. doi:
10.1016/j.bmcl.2004.01.069. [PMID: 15050644] - Rikke Louise Schrøder, Dorte Strøbaek, Søren-Peter Olesen, Palle Christophersen. Voltage-independent KCNQ4 currents induced by (+/-)BMS-204352.
Pflugers Archiv : European journal of physiology.
2003 Aug; 446(5):607-16. doi:
10.1007/s00424-003-1116-x. [PMID: 12851819] - Robert Hermann, Norbert G Knebel, Georg Niebch, Lyette Richards, Juergen Borlak, Mathias Locher. Pharmacokinetic interaction between retigabine and lamotrigine in healthy subjects.
European journal of clinical pharmacology.
2003 Apr; 58(12):795-802. doi:
10.1007/s00228-003-0558-6. [PMID: 12698305] - Songbai Zhang, Akihiro Mizutani, Chihiro Hisatsune, Takayasu Higo, Hiroko Bannai, Tomohiro Nakayama, Mitsuharu Hattori, Katsuhiko Mikoshiba. Protein 4.1N is required for translocation of inositol 1,4,5-trisphosphate receptor type 1 to the basolateral membrane domain in polarized Madin-Darby canine kidney cells.
The Journal of biological chemistry.
2003 Feb; 278(6):4048-56. doi:
10.1074/jbc.m209960200. [PMID: 12444087] - Robert Hermann, Geraldine M Ferron, Katharina Erb, Norbert Knebel, Peter Ruus, Jeffrey Paul, Lyette Richards, Hans-Peter Cnota, Steven Troy. Effects of age and sex on the disposition of retigabine.
Clinical pharmacology and therapeutics.
2003 Jan; 73(1):61-70. doi:
10.1067/mcp.2003.12. [PMID: 12545144] - G De Sarro, E D Di Paola, G Conte, M P Pasculli, A De Sarro. Influence of retigabine on the anticonvulsant activity of some antiepileptic drugs against audiogenic seizures in DBA/2 mice.
Naunyn-Schmiedeberg's archives of pharmacology.
2001 Mar; 363(3):330-6. doi:
10.1007/s002100000361. [PMID: 11284448] - N G Knebel, S Grieb, S Leisenheimer, M Locher. Determination of retigabine and its acetyl metabolite in biological matrices by on-line solid-phase extraction (column switching) liquid chromatography with tandem mass spectrometry.
Journal of chromatography. B, Biomedical sciences and applications.
2000 Oct; 748(1):97-111. doi:
10.1016/s0378-4347(00)00272-3. [PMID: 11092590] - R Hempel, H Schupke, P J McNeilly, K Heinecke, C Kronbach, C Grunwald, G Zimmermann, C Griesinger, J Engel, T Kronbach. Metabolism of retigabine (D-23129), a novel anticonvulsant.
Drug metabolism and disposition: the biological fate of chemicals.
1999 May; 27(5):613-22. doi:
NULL. [PMID: 10220491]
