Fexofenadine (BioDeep_00000002312)

 

Secondary id: BioDeep_00000229713, BioDeep_00000873153

human metabolite Endogenous blood metabolite Chemicals and Drugs natural product


代谢物信息卡片


4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetic acid

化学式: C32H39NO4 (501.28789340000003)
中文名称: 非索非那定
谱图信息: 最多检出来源 Homo sapiens(feces) 0.83%

分子结构信息

SMILES: CC(C)(C(=O)O)c1ccc(C(O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)cc1
InChI: InChI=1S/C32H39NO4/c1-31(2,30(35)36)25-17-15-24(16-18-25)29(34)14-9-21-33-22-19-28(20-23-33)32(37,26-10-5-3-6-11-26)27-12-7-4-8-13-27/h3-8,10-13,15-18,28-29,34,37H,9,14,19-23H2,1-2H3,(H,35,36)

描述信息

Fexofenadine is an antihistamine drug used in the treatment of hayfever and similar allergy symptoms. It was developed as a successor of and alternative to terfenadine, an antihistamine with potentially fatal contraindications. Fexofenadine, like other second-generation antihistamines, does not readily enter the brain from the blood, and so causes less drowsiness than first generation histamine receptor antagonists; Fexofenadine hydrochloride (brand names include Allegra and Telfast) is an antihistamine drug used in the treatment of hayfever and similar allergy symptoms. It was developed as a successor of and alternative to terfenadine, an antihistamine with potentially fatal contraindications. Fexofenadine, like other second generation antihistamines, does not readily enter the brain from the blood, and so causes less drowsiness than first-generation histamine-receptor antagonists.
R - Respiratory system > R06 - Antihistamines for systemic use > R06A - Antihistamines for systemic use
D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists
C308 - Immunotherapeutic Agent > C29578 - Histamine-1 Receptor Antagonist
D018926 - Anti-Allergic Agents
Fexofenadine (MDL-16455) is an orally active and nonsedative H1 receptor antagonist. Fexofenadine can be used in allergic rhinitis and chronic idiopathic urticarial research[1][2][3].

同义名列表

24 个代谢物同义名

4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetic acid; 4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetate; 2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid; 4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-α,α-dimethylbenzeneacetic acid; 4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-a,a-dimethylbenzeneacetic acid; 4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-a,a-dimethylbenzeneacetate; 4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-α,α-dimethylbenzeneacetate; alpha-(4-(1-Carboxy-1-methylethyl)phenyl)-4-hydroxydiphenylmethyl-1-piperidinebutanol; Aventis behring brand OF fexofenadine hydrochloride; Aventis pharma brand OF fexofenadine hydrochloride; Hoechst brand OF fexofenadine hydrochloride; Aventis brand OF fexofenadine hydrochloride; Terfenadine carboxylic acid; Terfenadine acid metabolite; Fexofenadine hydrochloride; Terfenadine carboxylate; Carboxyterfenadine; Terfenadine-COOH; fexofenadine; MDL 16,455a; Allegra; Telfast; MDL-16455; Fexofenadine



数据库引用编号

20 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)

6 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

  • Myriam El Biali, Michael Wölfl-Duchek, Matthias Jackwerth, Severin Mairinger, Maria Weber, Karsten Bamminger, Stefan Poschner, Ivo Rausch, Natalie Schindler, Irene Hernández Lozano, Walter Jäger, Lukas Nics, Nicolas Tournier, Marcus Hacker, Markus Zeitlinger, Martin Bauer, Oliver Langer. St. John's wort extract with a high hyperforin content does not induce P-glycoprotein activity at the human blood-brain barrier. Clinical and translational science. 2024 May; 17(5):e13804. doi: 10.1111/cts.13804. [PMID: 38700454]
  • Walaa A El-Dakroury, Moataz B Zewail, Gihan F Asaad, Heba M I Abdallah, Marwa E Shabana, Abdelrahman R Said, Ahmed S Doghish, Hadeer A Azab, Dalia H Amer, Ahmed E Hassan, Alaa S Sayed, Ghada M Samra, Al-Aliaa M Sallam. Fexofenadine-loaded chitosan coated solid lipid nanoparticles (SLNs): A potential oral therapy for ulcerative colitis. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2024 Mar; 196(?):114205. doi: 10.1016/j.ejpb.2024.114205. [PMID: 38311187]
  • Shingen Misaka, Yuko Ono, R Verena Taudte, Eva Hoier, Hiroshi Ogata, Tomoyuki Ono, Jörg König, Hiroshi Watanabe, Martin F Fromm, Kenju Shimomura. Exposure of Fexofenadine, but Not Pseudoephedrine, Is Markedly Decreased by Green Tea Extract in Healthy Volunteers. Clinical pharmacology and therapeutics. 2022 09; 112(3):627-634. doi: 10.1002/cpt.2682. [PMID: 35678032]
  • A Ningombam, S Handa, N Srivastava, R Mahajan, D De. Addition of oral fexofenadine to topical therapy leads to a significantly greater reduction in the serum interleukin-31 levels in mild to moderate paediatric atopic dermatitis. Clinical and experimental dermatology. 2022 Apr; 47(4):724-729. doi: 10.1111/ced.15032. [PMID: 34826148]
  • Amal A Sultan, Nourhan F El Nashar, Shimaa M Ashmawy, Gamal M El Maghraby. Cubosomes for Enhancing Intestinal Absorption of Fexofenadine Hydrochloride: In situ and in vivo Investigation. International journal of nanomedicine. 2022; 17(?):3543-3560. doi: 10.2147/ijn.s370235. [PMID: 35983479]
  • 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]
  • Qiu-Shi Xie, Jia-Xin Zhang, Ming Liu, Pei-Hua Liu, Zhong-Jian Wang, Liang Zhu, Ling Jiang, Meng-Meng Jin, Xiao-Nan Liu, Li Liu, Xiao-Dong Liu. Short-chain fatty acids exert opposite effects on the expression and function of p-glycoprotein and breast cancer resistance protein in rat intestine. Acta pharmacologica Sinica. 2021 Mar; 42(3):470-481. doi: 10.1038/s41401-020-0402-x. [PMID: 32555444]
  • Yingying Zhao, Zhimin Miao, Mingzhao Jiang, Xuan Zhou, Yong Lai. Effects of breviscapine and C3435T MDR1 gene polymorphism on the pharmacokinetics of fexofenadine, a P-glycoprotein substrate, in healthy volunteers. Xenobiotica; the fate of foreign compounds in biological systems. 2021 Mar; 51(3):366-372. doi: 10.1080/00498254.2020.1857467. [PMID: 33256506]
  • Alexey V Shchulkin, Yulia V Abalenikhina, Pelageya D Erokhina, Ivan V Chernykh, Elena N Yakusheva. The Role of P-Glycoprotein in Decreasing Cell Membranes Permeability during Oxidative Stress. Biochemistry. Biokhimiia. 2021 Feb; 86(2):197-206. doi: 10.1134/s0006297921020085. [PMID: 33832418]
  • Piñeyro-Garza Everardo, Gómez-Silva Magdalena, Gamino-Peña Maria Elena, Cohen-Muñoz Vanessa, Sánchez-Casado Gabriela. Bioavailability assessment of fexofenadine and montelukast in a fixed-dose combination tablet versus the components administered simultaneously. Allergologia et immunopathologia. 2021; 49(4):15-25. doi: 10.15586/aei.v49i4.89. [PMID: 34224214]
  • Erlend Johannessen Egeland, Bartlomiej J Witczak, Hasse Khiabani Zaré, Hege Christensen, Anders Åsberg, Ida Robertsen. Chronic Inhibition of CYP3A is Temporarily Reduced by Each Hemodialysis Session in Patients With End-Stage Renal Disease. Clinical pharmacology and therapeutics. 2020 10; 108(4):866-873. doi: 10.1002/cpt.1875. [PMID: 32356565]
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  • Leonardo Santos Ribeiro Pinto, Gabriel Tavares do Vale, Fernanda de Lima Moreira, Maria Paula Marques, Eduardo Barbosa Coelho, Ricardo Carvalho Cavalli, Vera Lucia Lanchote. Direct chiral LC-MS/MS analysis of fexofenadine enantiomers in plasma and urine with application in a maternal-fetal pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 May; 1145(?):122094. doi: 10.1016/j.jchromb.2020.122094. [PMID: 32311673]
  • Sara Batista do Nascimento, Mariana de Lima Nascimento, Laís Lobato de Araújo, Flávio Martins de Oliveira, Maria do Carmo Vieira, Joaquim Maurício Duarte-Almeida, João Máximo Siqueira, Isabela da Costa César, Hartmut Derendorf, Whocely Victor de Castro. Evaluation of the Effects of Maytenus ilicifolia on the Activities of Cytochrome P450 3A and P-glycoprotein. Current drug metabolism. 2020; 21(4):281-290. doi: 10.2174/1389200221666200512112718. [PMID: 32394829]
  • Diego A C Cusinato, Edson Z Martinez, Mônica T C Cintra, Gabriela C O Filgueira, Andresa A Berretta, Vera L Lanchote, Eduardo B Coelho. Evaluation of potential herbal-drug interactions of a standardized propolis extract (EPP-AF®) using an in vivo cocktail approach. Journal of ethnopharmacology. 2019 Dec; 245(?):112174. doi: 10.1016/j.jep.2019.112174. [PMID: 31442620]
  • Cheng-Zhi Huang, Zhi-Hui Jiang, Jian Wang, Yue Luo, Hua Peng. Antihistamine effects and safety of fexofenadine: a systematic review and Meta-analysis of randomized controlled trials. BMC pharmacology & toxicology. 2019 11; 20(1):72. doi: 10.1186/s40360-019-0363-1. [PMID: 31783781]
  • 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]
  • Samantha Medwid, Mandy M J Li, Michael J Knauer, Kathleen Lin, Sara E Mansell, Crystal L Schmerk, Catherine Zhu, Katelyn E Griffin, Mohamed D Yousif, George K Dresser, Ute I Schwarz, Richard B Kim, Rommel G Tirona. Fexofenadine and Rosuvastatin Pharmacokinetics in Mice with Targeted Disruption of Organic Anion Transporting Polypeptide 2B1. Drug metabolism and disposition: the biological fate of chemicals. 2019 08; 47(8):832-842. doi: 10.1124/dmd.119.087619. [PMID: 31123035]
  • Emiliano Calvo, Jong-Seok Lee, Sang-We Kim, Victor Moreno, Javier deCastro Carpeno, Doris Weilert, Gianluca Laus, Helen Mann, Karthick Vishwanathan. Modulation of Fexofenadine Pharmacokinetics by Osimertinib in Patients With Advanced EGFR-Mutated Non-Small Cell Lung Cancer. Journal of clinical pharmacology. 2019 08; 59(8):1099-1109. doi: 10.1002/jcph.1403. [PMID: 30875094]
  • Natalia Karolina Kordulewska, Elżbieta Kostyra, Barbara Chwała, Małgorzata Moszyńska, Anna Cieślińska, Ewa Fiedorowicz, Beata Jarmołowska. A novel concept of immunological and allergy interactions in autism spectrum disorders: Molecular, anti-inflammatory effect of osthole. International immunopharmacology. 2019 Jul; 72(?):1-11. doi: 10.1016/j.intimp.2019.01.058. [PMID: 30953868]
  • Diego Alberto Ciscato Cusinato, Gabriela Campos de Oliveira Filgueira, Adriana Rocha, Monica Akissue C T Cintra, Vera Lucia Lanchote, Eduardo Barbosa Coelho. LC-MS/MS analysis of the plasma concentrations of a cocktail of 5 cytochrome P450 and P-glycoprotein probe substrates and their metabolites using subtherapeutic doses. Journal of pharmaceutical and biomedical analysis. 2019 Feb; 164(?):430-441. doi: 10.1016/j.jpba.2018.10.029. [PMID: 30445356]
  • Alireza Derakhshan, Mahmood Khodadoost, Mostafa Ghanei, Latif Gachkar, Homa Hajimahdipour, Ali Taghipour, Jaleh Yousefi, Maryam Khoshkhui, Farahzad J Azad. Effects of a Novel Barley-Based Formulation on Allergic Rhinitis: A Randomized Controlled Trial. Endocrine, metabolic & immune disorders drug targets. 2019; 19(8):1224-1231. doi: 10.2174/1871530319666190306100611. [PMID: 30843497]
  • Michael J Myers, Marilyn Martinez, Fei Li, Karyn Howard, Haile F Yancy, Lisa Troutman, Michele Sharkey. Impact of ABCB1 genotype in Collies on the pharmacokinetics of R- and S-fexofenadine. Journal of veterinary pharmacology and therapeutics. 2018 Dec; 41(6):805-814. doi: 10.1111/jvp.12696. [PMID: 30020547]
  • Tsuyoshi Karibe, Tomoki Imaoka, Koji Abe, Osamu Ando. Curcumin as an In Vivo Selective Intestinal Breast Cancer Resistance Protein Inhibitor in Cynomolgus Monkeys. Drug metabolism and disposition: the biological fate of chemicals. 2018 05; 46(5):667-679. doi: 10.1124/dmd.117.078931. [PMID: 29358184]
  • Cecilie Hurup Munkboel, Stine Bjerregaard Hasselstrøm, David Møbjerg Kristensen, Bjarne Styrishave. Effects of antihistamines on the H295R steroidogenesis - Autocrine up-regulation following 3β-HSD inhibition. Toxicology in vitro : an international journal published in association with BIBRA. 2018 Apr; 48(?):302-309. doi: 10.1016/j.tiv.2018.01.026. [PMID: 29409762]
  • Yumiko Akamine, Masatomo Miura. An update on the clinical pharmacokinetics of fexofenadine enantiomers. Expert opinion on drug metabolism & toxicology. 2018 Apr; 14(4):429-434. doi: 10.1080/17425255.2018.1459565. [PMID: 29635947]
  • Kentaro Ando, Yuji Nakamura, Mihoko Hagiwara-Nagasawa, Hiroyuki Harada, Hiroyoshi Miyamoto, Naoki Inamura, Kan Takagi, Ai Goto, Koki Chiba, Nur Jaharat Lubna, Hiroko Izumi-Nakaseko, Atsuhiko T Naito, Atsushi Sugiyama. Comparison of electropharmacological effects between terfenadine and its active derivative fexofenadine using a cross-over study in halothane-anesthetized dogs to analyze variability of pharmacodynamic and pharmacokinetic profiles of terfenadine and torsadogenic risk of fexofenadine. The Journal of toxicological sciences. 2018; 43(3):183-192. doi: 10.2131/jts.43.183. [PMID: 29540652]
  • T Vanhove, T Bouillon, H de Loor, P Annaert, Drj Kuypers. Fexofenadine, a Putative In Vivo P-glycoprotein Probe, Fails to Predict Clearance of the Substrate Tacrolimus in Renal Recipients. Clinical pharmacology and therapeutics. 2017 Dec; 102(6):989-996. doi: 10.1002/cpt.718. [PMID: 28437851]
  • Jingjing Yu, Zhu Zhou, Jessica Tay-Sontheimer, René H Levy, Isabelle Ragueneau-Majlessi. Intestinal Drug Interactions Mediated by OATPs: A Systematic Review of Preclinical and Clinical Findings. Journal of pharmaceutical sciences. 2017 09; 106(9):2312-2325. doi: 10.1016/j.xphs.2017.04.004. [PMID: 28414144]
  • Meng Yan, Lifang Feng, Yanhui Shi, Junnan Wang, Yan Liu, Fengmei Li, Baoxin Li. Mechanism of As2O3-Induced Action Potential Prolongation and Using hiPS-CMs to Evaluate the Rescue Efficacy of Drugs With Different Rescue Mechanism. Toxicological sciences : an official journal of the Society of Toxicology. 2017 08; 158(2):379-390. doi: 10.1093/toxsci/kfx098. [PMID: 28521025]
  • Satish Kumar Bedada, Ramgopal Appani, Praveen Kumar Boga. Capsaicin pretreatment enhanced the bioavailability of fexofenadine in rats by P-glycoprotein modulation: in vitro, in situ and in vivo evaluation. Drug development and industrial pharmacy. 2017 Jun; 43(6):932-938. doi: 10.1080/03639045.2017.1285310. [PMID: 28102715]
  • Laxmi N Jattinagoudar, Sharanappa T Nandibewoor, Shivamurti A Chimatadar. Binding of fexofenadine hydrochloride to bovine serum albumin: structural considerations by spectroscopic techniques and molecular docking. Journal of biomolecular structure & dynamics. 2017 May; 35(6):1200-1214. doi: 10.1080/07391102.2016.1183229. [PMID: 27109454]
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  • Satish Kumar Bedada, Praveen Kumar Boga, Harish Kaushik Kotakonda. The effect of diosmin on the pharmacokinetics of fexofenadine in healthy human volunteers. Xenobiotica; the fate of foreign compounds in biological systems. 2017 Mar; 47(3):230-235. doi: 10.1080/00498254.2016.1180564. [PMID: 27151911]
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