Oxcarbazepine (BioDeep_00000001507)

 

Secondary id: BioDeep_00000398888

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


9-oxo-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide

化学式: C15H12N2O2 (252.0898732)
中文名称: 奥卡西平
谱图信息: 最多检出来源 Homo sapiens(blood) 1.15%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

Oxcarbazepine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/oxcarbazepine (retrieved 2024-11-08) (BioDeep RN: BioDeep_00000001507). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1C2=CC=CC=C2N(C3=CC=CC=C3C1=O)C(=O)N
InChI: InChI=1S/C15H12N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8H,9H2,(H2,16,19)

描述信息

Oxcarbazepine is structurally a derivative of carbamazepine, adding an extra oxygen atom to the benzylcarboxamide group. This difference helps reduce the impact on the liver of metabolizing the drug, and also prevents the serious forms of anemia occasionally associated with carbamazepine. Aside from this reduction in side effects, it is thought to have the same mechanism as carbamazepine - sodium channel inhibition - and is generally used to treat partial seizures in epileptic children and adults.
D002317 - Cardiovascular Agents > D026941 - Sodium Channel Blockers > D061567 - Voltage-Gated Sodium Channel Blockers
N - Nervous system > N03 - Antiepileptics > N03A - Antiepileptics > N03AF - Carboxamide derivatives
D065693 - Cytochrome P-450 Enzyme Inducers > D065701 - Cytochrome P-450 CYP3A Inducers
C78272 - Agent Affecting Nervous System > C264 - Anticonvulsant Agent
D002491 - Central Nervous System Agents > D000927 - Anticonvulsants
D049990 - Membrane Transport Modulators

同义名列表

11 个代谢物同义名

9-oxo-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide; 10,11-Dihydro-10-oxo-5H-dibenz(b,F)azepine-5-carboxamide; Novartis brand OF oxcarbazepine; Desitin brand OF oxcarbazepine; Oxcarbamazepine; Oxcarbazepinum; Oxcarbazepina; OXCARBAZEPINE; Trileptal; Oxtellar; Timox



数据库引用编号

16 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

1 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(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。



文献列表

  • Julija Čiauškaitė, Giedrė Gelžinienė, Giedrė Jurkevičienė. Oxcarbazepine and Hyponatremia. Medicina (Kaunas, Lithuania). 2022 Apr; 58(5):. doi: 10.3390/medicina58050559. [PMID: 35629976]
  • Page B Pennell, Ashwin Karanam, Kimford J Meador, Elizabeth Gerard, Laura Kalayjian, Patricia Penovich, Abigail Matthews, Thomas M McElrath, Angela K Birnbaum. Antiseizure Medication Concentrations During Pregnancy: Results From the Maternal Outcomes and Neurodevelopmental Effects of Antiepileptic Drugs (MONEAD) Study. JAMA neurology. 2022 04; 79(4):370-379. doi: 10.1001/jamaneurol.2021.5487. [PMID: 35157004]
  • Ahmet Burak Dirim, Safak Mirioglu, Nilufer Yesilot, Emin Oguz, Halil Yazici, Murat Inanc, Bahar Artim-Esen. Chronic oxcarbazepine intoxication in a patient with primary antiphospholipid syndrome on maintenance haemodialysis. Journal of clinical pharmacy and therapeutics. 2022 Feb; 47(2):257-259. doi: 10.1111/jcpt.13504. [PMID: 34322888]
  • Momoka Ota, Takeshi Funakoshi, Toshihiko Aki, Kana Unuma, Koichi Uemura. Oxcarbazepine induces mitotic catastrophe and apoptosis in NRK-52E proximal tubular cells. Toxicology letters. 2021 Oct; 350(?):240-248. doi: 10.1016/j.toxlet.2021.07.018. [PMID: 34333065]
  • Ana Ferreira, Márcio Rodrigues, Sara Meirinho, Ana Fortuna, Amílcar Falcão, Gilberto Alves. Silymarin as a flavonoid-type P-glycoprotein inhibitor with impact on the pharmacokinetics of carbamazepine, oxcarbazepine and phenytoin in rats. Drug and chemical toxicology. 2021 Sep; 44(5):458-469. doi: 10.1080/01480545.2019.1601736. [PMID: 31020859]
  • G Vartzelis, A Attilakos, C Tsentidis, I Kalimeraki, D Maritsi, A Marmarinos, A Garoufi. Plasma brain natriuretic peptide levels in children with idiopathic epilepsy treated with longterm sodium valproate and oxcarbazepine monotherapy. Journal of biological regulators and homeostatic agents. 2021 Aug; 35(4):. doi: 10.23812/21-126-l. [PMID: 34278773]
  • Karthik Rajendran, Bhadram Kalyan Chekraverthy, Rajendran Sankham Devendran, R Jasmin Sajini, Krishnaveni Nagappan. Simultaneous quantification of oxcarbazepine and its active metabolite in spiked human plasma using ultra performance liquid chromatography-MS/MS. Bioanalysis. 2021 Aug; 13(16):1259-1273. doi: 10.4155/bio-2021-0125. [PMID: 34463119]
  • Ting Zhao, Lu-Hai Yu, Ting-Ting Wang, Jie Feng, Long Ma, Jing Yu, Li Sun, Hong-Jian Li, Yan Sun. Development and validation of an innovative UPLC method to quantify lacosamide, oxcarbazepine, and lamotrigine in the serum of children with epilepsy in China. Biomedical chromatography : BMC. 2021 Apr; 35(4):e5022. doi: 10.1002/bmc.5022. [PMID: 33169403]
  • Yoonhyuk Jang, Seonghae Yoon, Tae-Joon Kim, SeungHwan Lee, Kyung-Sang Yu, In-Jin Jang, Kon Chu, Sang Kun Lee. Population pharmacokinetic model development and its relationship with adverse events of oxcarbazepine in adult patients with epilepsy. Scientific reports. 2021 03; 11(1):6370. doi: 10.1038/s41598-021-85920-0. [PMID: 33737678]
  • Bahareh Michelle Schweiger, Aaron-James Lao, Jane Tavyev. A Case Series of Patients With Central Hypothyroidism From Oxcarbazepine Therapy. Journal of child neurology. 2021 03; 36(3):237-242. doi: 10.1177/0883073820962926. [PMID: 33030389]
  • Reem Odi, Valentina Franco, Emilio Perucca, Meir Bialer. Bioequivalence and switchability of generic antiseizure medications (ASMs): A re-appraisal based on analysis of generic ASM products approved in Europe. Epilepsia. 2021 02; 62(2):285-302. doi: 10.1111/epi.16802. [PMID: 33426641]
  • Kai-Li Shi, Jun-Xiu Guo, Hui-Min Zhao, Han Hong, Chuan-Zi Yang, Yun-Hong Wu, Li-Jun Du. The effect of levetiracetam and oxcarbazepine monotherapy on thyroid hormones and bone metabolism in children with epilepsy: A prospective study. Epilepsy & behavior : E&B. 2020 12; 113(?):107555. doi: 10.1016/j.yebeh.2020.107555. [PMID: 33242769]
  • Sheng Feng, Brandi Bridgewater, Erin C Strickland, Gregory McIntire. A Rapid LC-MS-MS Method for the Quantitation of Antiepileptic Drugs in Urine. Journal of analytical toxicology. 2020 Oct; 44(7):688-696. doi: 10.1093/jat/bkaa095. [PMID: 32744607]
  • Elif Söylemez, Oya Öztürk, Sezin Alpaydın Baslo, Zeynep Ezgi Balçık, Dilek Ataklı. Metabolic syndrome and obstructive sleep apnea syndrome among patients with epilepsy on monotherapy. Epilepsy & behavior : E&B. 2020 10; 111(?):107296. doi: 10.1016/j.yebeh.2020.107296. [PMID: 32769040]
  • Sezin Erarpat, Süleyman Bodur, Merve Fırat Ayyıldız, Ömer Tahir Günkara, Fatih Erulaş, Dotse Selali Chormey, Fatma Turak, Türkan Börklü Budak, Sezgin Bakırdere. Accurate and simple determination of oxcarbazepine in human plasma and urine samples using switchable-hydrophilicity solvent in GC-MS. Biomedical chromatography : BMC. 2020 Oct; 34(10):e4915. doi: 10.1002/bmc.4915. [PMID: 32529647]
  • M Ley, A Principe, R Rocamora. [Long-term effects of dibenzazepines on metabolic parameters: retrospective comparison of carbamazepine, oxcarbazepine and eslicarbazepine acetate in the real world]. Revista de neurologia. 2020 Jul; 71(2):54-60. doi: 10.33588/rn.7102.2019207. [PMID: 32627160]
  • Anne Hagemann, Dennis Klimpel, Christian G Bien, Christian Brandt, Theodor W May. Influence of dose and antiepileptic comedication on brivaracetam serum concentrations in patients with epilepsy. Epilepsia. 2020 05; 61(5):e43-e48. doi: 10.1111/epi.16500. [PMID: 32304097]
  • Fanny Desbiolles, Xavier Moreau, Laetitia de Jong, Laure Malleret, Quentin Grandet-Marchant, Pascal Wong-Wah-Chung, Isabelle Laffont-Schwob. Advances and limits of two model species for ecotoxicological assessment of carbamazepine, two by-products and their mixture at environmental level in freshwater. Water research. 2020 Feb; 169(?):115267. doi: 10.1016/j.watres.2019.115267. [PMID: 31731244]
  • Shuzhang Zhang, Zhiping Zhang, Yuan Shen, Yudan Zhu, Kun Du, Jingkang Guo, Yonghua Ji, Jie Tao. SCN9A Epileptic Encephalopathy Mutations Display a Gain-of-function Phenotype and Distinct Sensitivity to Oxcarbazepine. Neuroscience bulletin. 2020 Jan; 36(1):11-24. doi: 10.1007/s12264-019-00413-5. [PMID: 31372899]
  • Katarzyna Socała, Elżbieta Wyska, Małgorzata Szafarz, Dorota Nieoczym, Piotr Wlaź. Acute effect of cannabidiol on the activity of various novel antiepileptic drugs in the maximal electroshock- and 6 Hz-induced seizures in mice: Pharmacodynamic and pharmacokinetic studies. Neuropharmacology. 2019 11; 158(?):107733. doi: 10.1016/j.neuropharm.2019.107733. [PMID: 31377197]
  • 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]
  • Lihua Qu, Lixuan Pan, Li Wang, Congmin Liu, Yanhong Tian, Zhihui Hao. Development of an online solid-phase extraction-liquid chromatography-mass spectrometric analysis of oxcarbazepine and its active metabolite licarbazepine from plasma with a direct injection step. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2019 Sep; 1125(?):121710. doi: 10.1016/j.jchromb.2019.06.037. [PMID: 31299362]
  • Ekram Nemr Abd-Al-Haleem, Shaimaa Salah Eldeen-Hussein, Hanan Abdel-Hameed Fahmy, Ragia Ali Mahmoud-Taha. Effect of gamma radiation on combination therapy of certain antiepileptic drugs in rats. Pakistan journal of pharmaceutical sciences. 2019 Jul; 32(4):1589-1597. doi: . [PMID: 31608878]
  • Manhua Liu, Yangyang Wang, Yueping Jiang, Haitao Liu, Jingjing Chen, Shao Liu. Quantitation of Oxcarbazepine Clinically in Plasma Using Surfaced-Enhanced Raman Spectroscopy (SERS) Coupled with Chemometrics. Applied spectroscopy. 2019 Jul; 73(7):801-809. doi: 10.1177/0003702819845389. [PMID: 30990054]
  • Michele Fabrazzo, Antonietta Fuschillo, Francesco Perris, Francesco Catapano. The unmasking of hidden severe hyponatremia after long-term combination therapy in exacerbated bipolar patients: a case series. International clinical psychopharmacology. 2019 07; 34(4):206-210. doi: 10.1097/yic.0000000000000265. [PMID: 30998596]
  • Chao-Yang Chen, Ying Zhou, Yi-Min Cui, Ting Yang, Xia Zhao, Ye Wu. Population pharmacokinetics and dose simulation of oxcarbazepine in Chinese paediatric patients with epilepsy. Journal of clinical pharmacy and therapeutics. 2019 Apr; 44(2):300-311. doi: 10.1111/jcpt.12792. [PMID: 30636182]
  • Xue Yang, Yuanliang Yan, Shu Fang, Shuangshuang Zeng, Hongying Ma, Long Qian, Xi Chen, Jie Wei, Zhicheng Gong, Zhijie Xu. Comparison of oxcarbazepine efficacy and MHD concentrations relative to age and BMI: Associations among ABCB1, ABCC2, UGT2B7, and SCN2A polymorphisms. Medicine. 2019 Mar; 98(12):e14908. doi: 10.1097/md.0000000000014908. [PMID: 30896644]
  • Xiaonian Han, Jing Huang, Jianhua Lv, Li Ma, Lirong Peng, Jinping Wang, Xiaojing Nie, Li Xia, Xin Zan. The influence of concomitant antiepileptic drugs on lamotrigine serum concentrations in Northwest Chinese Han population with epilepsy. PloS one. 2019; 14(1):e0210600. doi: 10.1371/journal.pone.0210600. [PMID: 30645607]
  • Yanan Chen, Shansen Xu, Zhanyou Wang, Mingming Zhao, Huanxin Wang, Tong Lu, Limei Zhao. A Population Pharmacokinetic-Pharmacogenetic Model of Lamotrigine in Chinese Children With Epilepsy. Therapeutic drug monitoring. 2018 12; 40(6):730-737. doi: 10.1097/ftd.0000000000000563. [PMID: 30169477]
  • Rituparna Maiti, Biswa Ranjan Mishra, Monalisa Jena, Archana Mishra, Santanu Nath, Anand Srinivasan. Effect of anti-seizure drugs on serum S100B in patients with focal seizure: a randomized controlled trial. Journal of neurology. 2018 Nov; 265(11):2594-2601. doi: 10.1007/s00415-018-9026-1. [PMID: 30173303]
  • Yuji Mano. LC-MS-MS Determination of Oxcarbazepine and an Active Metabolite in Human Plasma for Clinical Application. Journal of chromatographic science. 2018 Sep; 56(8):687-694. doi: 10.1093/chromsci/bmy040. [PMID: 29733349]
  • Michael J Palte, Sankha S Basu, Jameson L Dahlin, Ralitsa Gencheva, Donald Mason, Petr Jarolim, Athena K Petrides. Development and Validation of an Ultra-Performance Liquid Chromatography-Tandem Mass Spectrometry Method for the Concurrent Measurement of Gabapentin, Lamotrigine, Levetiracetam, Monohydroxy Derivative of Oxcarbazepine, and Zonisamide Concentrations in Serum in a Clinical Setting. Therapeutic drug monitoring. 2018 08; 40(4):469-476. doi: 10.1097/ftd.0000000000000516. [PMID: 29994986]
  • Ian R McGrane, Joshua G Loveland, Jose de Leon. Possible Oxcarbazepine Inductive Effects on Aripiprazole Metabolism: A Case Report. Journal of pharmacy practice. 2018 Jun; 31(3):361-363. doi: 10.1177/0897190017710523. [PMID: 28539103]
  • Natalícia de Jesus Antunes, Lauro Wichert-Ana, Eduardo Barbosa Coelho, Oscar Della Pasqua, Veriano Alexandre Junior, Osvaldo Massaiti Takayanagui, Maria Paula Marques, Vera Lucia Lanchote. Analysis of unbound plasma concentration of oxcarbazepine and the 10-hydroxycarbazepine enantiomers by liquid chromatography with tandem mass spectrometry in healthy volunteers. Journal of pharmaceutical and biomedical analysis. 2018 Feb; 149(?):442-447. doi: 10.1016/j.jpba.2017.11.041. [PMID: 29169112]
  • Rita Moretti, Paola Caruso, Matteo Dal Ben, Silvia Gazzin, Claudio Tiribelli. Hepatitis C-related cryoglobulinemic neuropathy: potential role of oxcarbazepine for pain control. BMC gastroenterology. 2018 Jan; 18(1):19. doi: 10.1186/s12876-018-0751-9. [PMID: 29370761]
  • Christelle Rodrigues, Catherine Chiron, Elisabeth Rey, Olivier Dulac, Emmanuelle Comets, Gérard Pons, Vincent Jullien. Population pharmacokinetics of oxcarbazepine and its monohydroxy derivative in epileptic children. British journal of clinical pharmacology. 2017 12; 83(12):2695-2708. doi: 10.1111/bcp.13392. [PMID: 28771787]
  • Rituparna Maiti, Biswa Ranjan Mishra, Soham Sanyal, Debadatta Mohapatra, Sansita Parida, Archana Mishra. Effect of carbamazepine and oxcarbazepine on serum neuron-specific enolase in focal seizures: A randomized controlled trial. Epilepsy research. 2017 12; 138(?):5-10. doi: 10.1016/j.eplepsyres.2017.10.003. [PMID: 29028517]
  • Monica Puligheddu, Miriam Melis, Giuliano Pillolla, Giulia Milioli, Liborio Parrino, Giovanni Mario Terzano, Sonia Aroni, Claudia Sagheddu, Francesco Marrosu, Marco Pistis, Anna Lisa Muntoni. Rationale for an adjunctive therapy with fenofibrate in pharmacoresistant nocturnal frontal lobe epilepsy. Epilepsia. 2017 10; 58(10):1762-1770. doi: 10.1111/epi.13863. [PMID: 28766701]
  • Chunhong Shen, Bijun Zhang, Zhirong Liu, Yelei Tang, Yinxi Zhang, Shan Wang, Yi Guo, Yao Ding, Shuang Wang, Meiping Ding. Effects of ABCB1, ABCC2, UGT2B7 and HNF4α genetic polymorphisms on oxcarbazepine concentrations and therapeutic efficacy in patients with epilepsy. Seizure. 2017 Oct; 51(?):102-106. doi: 10.1016/j.seizure.2017.07.015. [PMID: 28837897]
  • Elias Begas, Andreas Tsakalof, Efthimios Dardiotis, Georgios Emmanouil Vatidis, Evangelos Kouvaras, Eftihia Konstadinos Asprodini. Development and validation of a reversed-phase HPLC method for licarbazepine monitoring in serum of patients under oxcarbazepine treatment. Biomedical chromatography : BMC. 2017 Sep; 31(9):. doi: 10.1002/bmc.3950. [PMID: 28182284]
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  • Annika Sattler, Marion Schaefer, Theodor W May. Relationship between mono-hydroxy-carbazepine serum concentrations and adverse effects in patients on oxcarbazepine monotherapy. Seizure. 2015 Sep; 31(?):149-54. doi: 10.1016/j.seizure.2015.07.018. [PMID: 26362393]
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