Felbamate (BioDeep_00000001967)

 

Secondary id: BioDeep_00000398873

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


Carbamic acid 3-carbamoyloxy-2-phenyl-propyl ester

化学式: C11H14N2O4 (238.0954)
中文名称: 非氨酯, 氨基甲酸酯
谱图信息: 最多检出来源 Homo sapiens(blood) 22.41%

分子结构信息

SMILES: C1=CC=C(C=C1)C(COC(=O)N)COC(=O)N
InChI: InChI=1S/C11H14N2O4/c12-10(14)16-6-9(7-17-11(13)15)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,12,14)(H2,13,15)

描述信息

Felbamate is an anticonvulsant drug used in the treatment of epilepsy. It is used to treat partial seizures (with and without generalization) in adults and partial and generalized seizures associated with Lennox-Gastaut syndrome in children. It has a weak inhibitory effect on GABA receptor binding sites.
D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018691 - Excitatory Amino Acid Antagonists
C78272 - Agent Affecting Nervous System > C264 - Anticonvulsant Agent
D002491 - Central Nervous System Agents > D000927 - Anticonvulsants
N - Nervous system > N03 - Antiepileptics > N03A - Antiepileptics
Felbamate (W-554) is a potent nonsedative anticonvulsant whose clinical effect may be related to the inhibition of N-methyl-D-aspartate (NMDA).

同义名列表

22 个代谢物同义名

Carbamic acid 3-carbamoyloxy-2-phenyl-propyl ester; Carbamate 3-carbamoyloxy-2-phenyl-propyl ester; (3-Carbamoyloxy-2-phenyl-propyl) carbamate; 3-(carbamoyloxy)-2-phenylpropyl carbamate; 2-Phenyl-1,3-propanediol dicarbamic acid; Carbamic acid 2-phenyltrimethylene ester; 2-Phenyl-1,3-propanediol dicarbamate; Carbamate 2-phenyltrimethylene ester; 2 Phenyl 1,3 propanediol dicarbamate; Wallace brand 2 OF felbamate; Wallace brand 1 OF felbamate; Felbamic acid; Felbamatum; felbamate; Felbamato; Felbatol; Felbamyl; Taloxa; W-554; ADD-03055; Felbamate; Felbamate



数据库引用编号

18 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

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(2)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(1)

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。

亚细胞结构定位 关联基因列表
Cytoplasm 11 ABCB1, ALB, AXIN2, CA1, CA2, CYP2C19, CYP2C9, CYP2E1, CYP3A4, POMC, TSC1
Peripheral membrane protein 3 CYP1B1, CYP2E1, TSC1
Endoplasmic reticulum membrane 6 CYP1A2, CYP1B1, CYP2C19, CYP2C9, CYP2E1, CYP3A4
Nucleus 3 ALB, AXIN2, TSC1
cytosol 5 ALB, AXIN2, CA1, CA2, TSC1
centrosome 2 ALB, AXIN2
nucleoplasm 1 SCNN1G
Cell membrane 4 ABCB1, CA2, GLRA2, GRID1
lamellipodium 1 TSC1
Multi-pass membrane protein 5 ABCB1, CACNA1I, GLRA2, GRID1, SCNN1G
Synapse 1 GLRA2
cell cortex 1 TSC1
cell surface 1 ABCB1
glutamatergic synapse 1 GRID1
Golgi apparatus 1 ALB
lysosomal membrane 1 TSC1
mitochondrial inner membrane 1 CYP2E1
Cytoplasm, cytosol 1 TSC1
plasma membrane 10 ABCB1, AXIN2, CA2, CACNA1I, CYP2C19, CYP2C9, GLRA2, GRID1, SCNN1G, TSC1
Membrane 6 ABCB1, CACNA1I, CYP1B1, CYP3A4, GLRA2, TSC1
apical plasma membrane 2 ABCB1, SCNN1G
extracellular exosome 6 ABCB1, ALB, CA1, CA2, GRID1, SCNN1G
Lysosome membrane 1 TSC1
endoplasmic reticulum 1 ALB
extracellular space 3 ALB, IL4, POMC
perinuclear region of cytoplasm 1 TSC1
mitochondrion 2 ABAT, CYP1B1
protein-containing complex 2 ALB, TSC1
intracellular membrane-bounded organelle 7 CYP1A2, CYP1B1, CYP2C19, CYP2C9, CYP2E1, CYP3A4, GLRA2
Microsome membrane 5 CYP1A2, CYP1B1, CYP2C9, CYP2E1, CYP3A4
postsynaptic density 1 TSC1
Secreted 4 ALB, IL4, POMC, TRH
extracellular region 4 ALB, IL4, POMC, TRH
mitochondrial matrix 1 ABAT
anchoring junction 1 ALB
external side of plasma membrane 1 SCNN1G
beta-catenin destruction complex 1 AXIN2
apical part of cell 1 CA2
postsynaptic membrane 1 GRID1
Apical cell membrane 2 ABCB1, SCNN1G
Mitochondrion inner membrane 1 CYP2E1
GABA-ergic synapse 2 GLRA2, GRID1
secretory granule 2 POMC, TRH
Postsynaptic cell membrane 2 GLRA2, GRID1
neuron projection 1 GLRA2
ciliary basal body 1 ALB
cell projection 1 GLRA2
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
transmembrane transporter complex 1 GLRA2
Lipid droplet 1 TSC1
chloride channel complex 1 GLRA2
sodium channel complex 1 SCNN1G
myelin sheath 1 CA2
secretory granule lumen 1 POMC
endoplasmic reticulum lumen 1 ALB
platelet alpha granule lumen 1 ALB
voltage-gated calcium channel complex 1 CACNA1I
postsynaptic density membrane 1 GRID1
protein folding chaperone complex 1 TSC1
external side of apical plasma membrane 1 ABCB1
postsynaptic specialization membrane 1 GLRA2
glycinergic synapse 1 GLRA2
ciliary transition fiber 1 ALB
TSC1-TSC2 complex 1 TSC1
4-aminobutyrate transaminase complex 1 ABAT


文献列表

  • Koya Sato, Seigo Sanoh, Yuji Ishida, Chise Tateno, Shigeru Ohta, Yaichiro Kotake. Assessment of metabolic activation of felbamate in chimeric mice with humanized liver in combination with in vitro metabolic assays. The Journal of toxicological sciences. 2022; 47(7):277-288. doi: 10.2131/jts.47.277. [PMID: 35786679]
  • 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]
  • Xiaoyang Li, Richard A Himes, Lyndsey C Prosser, Charleston F Christie, Emma Watt, Sharon F Edwards, Cameron S Metcalf, Peter J West, Karen S Wilcox, Sherine S L Chan, C James Chou. Discovery of the First Vitamin K Analogue as a Potential Treatment of Pharmacoresistant Seizures. Journal of medicinal chemistry. 2020 06; 63(11):5865-5878. doi: 10.1021/acs.jmedchem.0c00168. [PMID: 32390424]
  • Xiuqin Li, Hongze Wang, Qingnian Chen, Zhiqin Li, Chao Liu, Shengnan Yin, Zhengchen You. Felbamate produces antidepressant-like actions in the chronic unpredictable mild stress and chronic social defeat stress models of depression. Fundamental & clinical pharmacology. 2019 Dec; 33(6):621-633. doi: 10.1111/fcp.12466. [PMID: 30951217]
  • 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]
  • 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]
  • Frida Gustafsson, Alison J Foster, Sunil Sarda, Matthew H Bridgland-Taylor, J Gerry Kenna. A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans. Toxicological sciences : an official journal of the Society of Toxicology. 2014 Jan; 137(1):189-211. doi: 10.1093/toxsci/kft223. [PMID: 24085192]
  • Mai Shibata, Sachiyo Hashi, Haruka Nakanishi, Satohiro Masuda, Toshiya Katsura, Ikuko Yano. Detection of 22 antiepileptic drugs by ultra-performance liquid chromatography coupled with tandem mass spectrometry applicable to routine therapeutic drug monitoring. Biomedical chromatography : BMC. 2012 Dec; 26(12):1519-28. doi: 10.1002/bmc.2726. [PMID: 22383262]
  • Daniel J Warner, Hongming Chen, Louis-David Cantin, J Gerry Kenna, Simone Stahl, Clare L Walker, Tobias Noeske. Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification. Drug metabolism and disposition: the biological fate of chemicals. 2012 Dec; 40(12):2332-41. doi: 10.1124/dmd.112.047068. [PMID: 22961681]
  • Mark Walzer, Ihor Bekersky, Robert A Blum, Dwain Tolbert. Pharmacokinetic drug interactions between clobazam and drugs metabolized by cytochrome P450 isoenzymes. Pharmacotherapy. 2012 Apr; 32(4):340-53. doi: 10.1002/j.1875-9114.2012.01028.x. [PMID: 22422635]
  • Giovambattista De Sarro, Eugenio Donato Di Paola, Santo Gratteri, Pietro Gareri, Vincenzo Rispoli, Antonio Siniscalchi, Giovanni Tripepi, Luca Gallelli, Rita Citraro, Emilio Russo. Fosinopril and zofenopril, two angiotensin-converting enzyme (ACE) inhibitors, potentiate the anticonvulsant activity of antiepileptic drugs against audiogenic seizures in DBA/2 mice. Pharmacological research. 2012 Mar; 65(3):285-96. doi: 10.1016/j.phrs.2011.11.005. [PMID: 22107891]
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  • Sarah Dawson, Simone Stahl, Nikki Paul, Jane Barber, J Gerald Kenna. In vitro inhibition of the bile salt export pump correlates with risk of cholestatic drug-induced liver injury in humans. Drug metabolism and disposition: the biological fate of chemicals. 2012 Jan; 40(1):130-8. doi: 10.1124/dmd.111.040758. [PMID: 21965623]
  • Adak Nasiripourdori, Valérie Taly, Thomas Grutter, Antoine Taly. From toxins targeting ligand gated ion channels to therapeutic molecules. Toxins. 2011 03; 3(3):260-93. doi: 10.3390/toxins3030260. [PMID: 22069709]
  • Bartłomiej Barczyński, Grzegorz Buszewicz, Jarogniew J Łuszczki, Krzysztof Bańka, Krzysztof Tutaj, Tomasz Mróz, Marian Wielosz, Roman Mądro, Piotr Tutka. Low dose of bupropion significantly enhances the anticonvulsant activity of felbamate, lamotrigine and topiramate in mice. European journal of pharmacology. 2011 Jan; 650(2-3):550-5. doi: 10.1016/j.ejphar.2010.10.039. [PMID: 21034737]
  • Muhannad R M Salih, Mohd Baidi Bahari, Arwa Y Abd. Selected pharmacokinetic issues of the use of antiepileptic drugs and parenteral nutrition in critically ill patients. Nutrition journal. 2010 Dec; 9(?):71. doi: 10.1186/1475-2891-9-71. [PMID: 21194458]
  • Ryan J Hansen, Bradley J Samber, Daniel L Gustafson. Rapid and sensitive LC-MS/MS method for determination of felbamate in mouse plasma and tissues and human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Dec; 878(32):3432-6. doi: 10.1016/j.jchromb.2010.10.006. [PMID: 21081288]
  • Xavier Parent, Franz Schieffer. [Felbamate crystalluria]. Annales de biologie clinique. 2010 Sep; 68(5):609-13. doi: 10.1684/abc.2010.0469. [PMID: 20870585]
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  • Courtney Heideloff, Dustin R Bunch, Sihe Wang. A novel HPLC method for quantification of 10 antiepileptic drugs or metabolites in serum/plasma using a monolithic column. Therapeutic drug monitoring. 2010 Feb; 32(1):102-6. doi: 10.1097/ftd.0b013e3181c324c8. [PMID: 19927045]
  • Manuela Contin, Susan Mohamed, Carmina Candela, Fiorenzo Albani, Roberto Riva, Agostino Baruzzi. Simultaneous HPLC-UV analysis of rufinamide, zonisamide, lamotrigine, oxcarbazepine monohydroxy derivative and felbamate in deproteinized plasma of patients with epilepsy. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Feb; 878(3-4):461-5. doi: 10.1016/j.jchromb.2009.11.039. [PMID: 20005185]
  • Olivier Tribut, Danièle Bentué-Ferrer, Marie-Clémence Verdier. [Therapeutic drug monitoring of felbamate]. Therapie. 2010 Jan; 65(1):35-8. doi: 10.2515/therapie/2009068. [PMID: 20205993]
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  • Andrea Domenico Praticò, Piero Pavone, Maria Grazia Scuderi, Giovanni Li Volti, Renato Bernardini, Giuseppina Cantarella, Lorenzo Pavone. Symptomatic hypocalcemia in an epileptic child treated with valproic acid plus lamotrigine: a case report. Cases journal. 2009 Jun; 2(?):7394. doi: 10.4076/1757-1626-2-7394. [PMID: 19829950]
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  • Peter H Tang. Drug monitoring and toxicology: a simple procedure for the monitoring of felbamate by HPLC-UV detection. Journal of analytical toxicology. 2008 Jun; 32(5):373-8. doi: 10.1093/jat/32.5.373. [PMID: 18544223]
  • Agnieszka Basta-Kaim, Bogusława Budziszewska, Władysław Lasoń. [Effects of antiepileptic drugs on immune system]. Przeglad lekarski. 2008; 65(11):799-802. doi: . [PMID: 19205364]
  • V K Gupta, A K Singh, Barkha Gupta. Development of membrane electrodes for selective determination of some antiepileptic drugs in pharmaceuticals, plasma and urine. Analytical and bioanalytical chemistry. 2007 Nov; 389(6):2019-28. doi: 10.1007/s00216-007-1560-0. [PMID: 17874084]
  • Eugenio Donato Di Paola, Pietro Gareri, Alessandro Davoli, Santo Gratteri, Francesca Scicchitano, Clara Naccari, Giovambattista De Sarro. Influence of levetiracetam on the anticonvulsant efficacy of conventional antiepileptic drugs against audiogenic seizures in DBA/2 mice. Epilepsy research. 2007 Jul; 75(2-3):112-21. doi: 10.1016/j.eplepsyres.2007.04.008. [PMID: 17553669]
  • Masato Matsuura. [Newer antiepileptic drugs]. No to shinkei = Brain and nerve. 2007 Feb; 59(2):147-56. doi: . [PMID: 17315756]
  • Masato Matsuura. [Newer antiepileptic drugs]. Brain and nerve = Shinkei kenkyu no shinpo. 2007 Feb; 59(2):147-56. doi: NULL. [PMID: 17380779]
  • Glenda Lacerda, Thierry Krummel, Cécile Sabourdy, Philippe Ryvlin, Edouard Hirsch. Optimizing therapy of seizures in patients with renal or hepatic dysfunction. Neurology. 2006 Dec; 67(12 Suppl 4):S28-33. doi: 10.1212/wnl.67.12_suppl_4.s28. [PMID: 17190918]
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  • Manuela Contin, Monica Balboni, Erica Callegati, Carmina Candela, Fiorenzo Albani, Roberto Riva, Agostino Baruzzi. Simultaneous liquid chromatographic determination of lamotrigine, oxcarbazepine monohydroxy derivative and felbamate in plasma of patients with epilepsy. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Dec; 828(1-2):113-7. doi: 10.1016/j.jchromb.2005.09.009. [PMID: 16182617]
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  • Jarogniew J Luszczki, Stanislaw J Czuczwar. Interaction between lamotrigine and felbamate in the maximal electroshock-induced seizures in mice: an isobolographic analysis. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology. 2005 Mar; 15(2):133-42. doi: 10.1016/j.euroneuro.2004.06.002. [PMID: 15695057]
  • Vincenzo Pucci, Maria Augusta Raggi. Analysis of antiepileptic drugs in biological fluids by means of electrokinetic chromatography. Electrophoresis. 2005 Feb; 26(4-5):767-82. doi: 10.1002/elps.200410207. [PMID: 15714570]
  • Kathryn H Meier, Kent R Olson, Jean L Olson. Acute felbamate overdose with crystalluria. Clinical toxicology (Philadelphia, Pa.). 2005; 43(3):189-92. doi: . [PMID: 15902793]
  • Klaus Turnheim. [Drug interactions with antiepileptic agents]. Wiener klinische Wochenschrift. 2004 Feb; 116(4):112-8. doi: 10.1007/bf03040747. [PMID: 15038401]
  • Pietro Gareri, Daniele Condorelli, Natale Belluardo, Santo Gratteri, Guido Ferreri, Eugenio Donato Di Paola, Angela De Sarro, Giovambattista De Sarro. Influence of carbenoxolone on the anticonvulsant efficacy of conventional antiepileptic drugs against audiogenic seizures in DBA/2 mice. European journal of pharmacology. 2004 Jan; 484(1):49-56. doi: 10.1016/j.ejphar.2003.10.047. [PMID: 14729381]
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  • Heidrun Potschka, Maren Fedrowitz, Wolfgang Löscher. Brain access and anticonvulsant efficacy of carbamazepine, lamotrigine, and felbamate in ABCC2/MRP2-deficient TR- rats. Epilepsia. 2003 Dec; 44(12):1479-86. doi: 10.1111/j.0013-9580.2003.22603.x. [PMID: 14636316]
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  • Shane G Roller, Christine M Dieckhaus, Webster L Santos, R Duane Sofia, Timothy L Macdonald. Interaction between human serum albumin and the felbamate metabolites 4-Hydroxy-5-phenyl-[1,3]oxazinan-2-one and 2-phenylpropenal. Chemical research in toxicology. 2002 Jun; 15(6):815-24. doi: 10.1021/tx025509h. [PMID: 12067249]
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