Zafirlukast (BioDeep_00000003192)

 

Secondary id: BioDeep_00000398936

human metabolite blood metabolite


代谢物信息卡片


[3-[[2-methoxy-4-[[[(2-methylphenyl)sulfonyl]amino]carbonyl]phenyl]methyl]-1-methyl-1H-indol-5-yl]-carbamic acid, cyclopentyl ester

化学式: C31H33N3O6S (575.209)
中文名称: 扎鲁斯特
谱图信息: 最多检出来源 Mentha canadensis(plant) 41.33%

分子结构信息

SMILES: CC1=CC=CC=C1S(=O)(=O)NC(=O)C2=CC(=C(C=C2)CC3=CN(C4=C3C=C(C=C4)NC(=O)OC5CCCC5)C)OC
InChI: InChI=1S/C31H33N3O6S/c1-20-8-4-7-11-29(20)41(37,38)33-30(35)22-13-12-21(28(17-22)39-3)16-23-19-34(2)27-15-14-24(18-26(23)27)32-31(36)40-25-9-5-6-10-25/h4,7-8,11-15,17-19,25H,5-6,9-10,16H2,1-3H3,(H,32,36)(H,33,35)

描述信息

Zafirlukast is an oral leukotriene receptor antagonist (LTRA) for the maintenance treatment of asthma, often used in conjunction with an inhaled steroid and/or long-acting bronchodilator. It is available as a tablet and is usually dosed twice daily. Another leukotriene receptor antagonist is montelukast (Singulair), which is usually taken just once daily. Zafirlukast blocks the action of the cysteinyl leukotrienes on the CysLT1 receptors, thus reducing constriction of the airways, build-up of mucus in the lungs and inflammation of the breathing passages.
R - Respiratory system > R03 - Drugs for obstructive airway diseases > R03D - Other systemic drugs for obstructive airway diseases > R03DC - Leukotriene receptor antagonists
D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D020024 - Leukotriene Antagonists
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists
C78273 - Agent Affecting Respiratory System > C29712 - Anti-asthmatic Agent

同义名列表

15 个代谢物同义名

[3-[[2-methoxy-4-[[[(2-methylphenyl)sulfonyl]amino]carbonyl]phenyl]methyl]-1-methyl-1H-indol-5-yl]-carbamic acid, cyclopentyl ester; cyclopentyl N-[3-({2-methoxy-4-[(2-methylbenzenesulfonyl)carbamoyl]phenyl}methyl)-1-methyl-1H-indol-5-yl]carbamate; 4-(5-Cyclopentyloxycarbonylamino-1-methyl-1H-indol-3-ylmethyl)-3-methoxy-N-O-tolylsulphonylbenzamide; 4-(5-Cyclopentyloxycarbonylamino-1-methyl-1H-indol-3-ylmethyl)-3-methoxy-N-O-tolylsulfonylbenzamide; 4-(5-Cyclopentyloxycarbonylamino-2-methylindol-3-yl-methyl)-3-methoxy-N-O-tolylsulfonylbenzamide; Cyclopentyl 3-(2-methoxy-4-((O-tolylsulphonyl)carbamoyl)benzyl)-1-methylindole-5-carbamic acid; Cyclopentyl 3-(2-methoxy-4-((O-tolylsulfonyl)carbamoyl)benzyl)-1-methylindole-5-carbamic acid; Cyclopentyl 3-(2-methoxy-4-((O-tolylsulphonyl)carbamoyl)benzyl)-1-methylindole-5-carbamate; Cyclopentyl 3-(2-methoxy-4-((O-tolylsulfonyl)carbamoyl)benzyl)-1-methylindole-5-carbamate; Accolic acid; zafirlukast; Accolate; Aeronix; Olmoran; Zafirlukast



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

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。

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亚细胞结构定位 关联基因列表
Cytoplasm 8 ALOX5, BCL2, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP2E1, CYP3A4
Peripheral membrane protein 3 ALOX5, CYP1B1, CYP2E1
Endoplasmic reticulum membrane 9 BCL2, CYP1A2, CYP1B1, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP2E1, CYP3A4
Nucleus 3 BCL2, LMNA, MPO
cytosol 4 ALOX5, BCL2, EPHX2, LMNA
nucleoplasm 3 ALOX5, LMNA, MPO
Cell membrane 2 CYSLTR2, TNF
Multi-pass membrane protein 1 CYSLTR2
cell surface 1 TNF
mitochondrial inner membrane 1 CYP2E1
neuronal cell body 1 TNF
Cytoplasm, cytosol 1 ALOX5
Lysosome 1 MPO
plasma membrane 7 CYP2C19, CYP2C8, CYP2C9, CYSLTR1, CYSLTR2, IGHE, TNF
Membrane 5 BCL2, CYP1B1, CYP2D6, CYP3A4, CYSLTR1
extracellular exosome 2 EPHX2, MPO
endoplasmic reticulum 2 BCL2, CYP2D6
extracellular space 7 ALOX5, IGHE, IL4, IL6, MPO, RNASE3, TNF
perinuclear region of cytoplasm 2 ALOX5, LMNA
mitochondrion 3 BCL2, CYP1B1, CYP2D6
protein-containing complex 1 BCL2
intracellular membrane-bounded organelle 9 CYP1A2, CYP1B1, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP2E1, CYP3A4, MPO
Microsome membrane 6 CYP1A2, CYP1B1, CYP2C9, CYP2D6, CYP2E1, CYP3A4
Single-pass type I membrane protein 1 IGHE
Secreted 2 IL4, IL6
extracellular region 7 ALOX5, IGHE, IL4, IL6, MPO, RNASE3, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 2 BCL2, CYP2D6
mitochondrial outer membrane 1 BCL2
Nucleus membrane 2 ALOX5, BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 3 ALOX5, BCL2, LMNA
external side of plasma membrane 1 TNF
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cytoplasm, perinuclear region 1 ALOX5
Mitochondrion inner membrane 1 CYP2E1
Membrane raft 1 TNF
pore complex 1 BCL2
Peroxisome 1 EPHX2
peroxisomal matrix 1 EPHX2
secretory granule 1 MPO
intermediate filament 1 LMNA
nuclear speck 1 LMNA
IgE immunoglobulin complex 1 IGHE
phagocytic cup 1 TNF
[Isoform 2]: Cell membrane 1 IGHE
site of double-strand break 1 LMNA
nuclear envelope 2 ALOX5, LMNA
Nucleus envelope 2 ALOX5, LMNA
Nucleus, nucleoplasm 1 LMNA
myelin sheath 1 BCL2
azurophil granule 1 MPO
ficolin-1-rich granule lumen 1 ALOX5
secretory granule lumen 1 ALOX5
endoplasmic reticulum lumen 1 IL6
nuclear matrix 2 ALOX5, LMNA
azurophil granule lumen 2 MPO, RNASE3
Nucleus matrix 2 ALOX5, LMNA
nuclear envelope lumen 1 ALOX5
nuclear lamina 1 LMNA
phagocytic vesicle lumen 1 MPO
[Isoform 3]: Cell membrane 1 IGHE
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
Nucleus lamina 1 LMNA
[Isoform C]: Nucleus speckle 1 LMNA
lamin filament 1 LMNA
interleukin-6 receptor complex 1 IL6
Nucleus intermembrane space 1 ALOX5
BAD-BCL-2 complex 1 BCL2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Wenxin Huang, Jia-Xi Wang, Xiaofei Shen, Yuqin Lei, Xueqin Chen, Da Jia, Xia Zhang, Qingxiang Sun. Searching for Novel Noncovalent Nuclear Export Inhibitors through a Drug Repurposing Approach. Journal of medicinal chemistry. 2023 01; 66(2):1574-1582. doi: 10.1021/acs.jmedchem.2c01772. [PMID: 36622814]
  • Christopher Wolf, Sonja Smith, Sjoerd J L van Wijk. Zafirlukast Induces VHL- and HIF-2α-Dependent Oxidative Cell Death in 786-O Clear Cell Renal Carcinoma Cells. International journal of molecular sciences. 2022 Mar; 23(7):. doi: 10.3390/ijms23073567. [PMID: 35408930]
  • Yuanying Fang, Lamees Hegazy, Brian N Finck, Bahaa Elgendy. Recent Advances in the Medicinal Chemistry of Farnesoid X Receptor. Journal of medicinal chemistry. 2021 12; 64(24):17545-17571. doi: 10.1021/acs.jmedchem.1c01017. [PMID: 34889100]
  • N Mehyar, A Mashhour, I Islam, H A Alhadrami, A M Tolah, B Alghanem, S Alkhaldi, B A Somaie, M Al Ghobain, Y Alobaida, A S Alaskar, M Boudjelal. Discovery of Zafirlukast as a novel SARS-CoV-2 helicase inhibitor using in silico modelling and a FRET-based assay. SAR and QSAR in environmental research. 2021 Dec; 32(12):963-983. doi: 10.1080/1062936x.2021.1993995. [PMID: 34818959]
  • 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]
  • Qiang Song, Zhi Hu, Xinming Xie, Hui Cai. Zafirlukast prevented ox-LDL-induced formation of foam cells. Toxicology and applied pharmacology. 2020 12; 409(?):115295. doi: 10.1016/j.taap.2020.115295. [PMID: 33096109]
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  • Pranesh Kumar, Aakriti Agarwal, Ashok K Singh, Anurag Kumar Gautam, Sreemoyee Chakraborti, Umesh Kumar, Dinesh Kumar, Bolay Bhattacharya, Parthasarathi Panda, Biswajit Saha, Tabish Qidwai, Biswanath Maity, Sudipta Saha. Antineoplastic properties of zafirlukast against hepatocellular carcinoma via activation of mitochondrial mediated apoptosis. Regulatory toxicology and pharmacology : RTP. 2019 Dec; 109(?):104489. doi: 10.1016/j.yrtph.2019.104489. [PMID: 31605713]
  • 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]
  • Eric E Figueroa, Meghan Kramer, Kevin Strange, Jerod S Denton. CysLT1 receptor antagonists pranlukast and zafirlukast inhibit LRRC8-mediated volume regulated anion channels independently of the receptor. American journal of physiology. Cell physiology. 2019 10; 317(4):C857-C866. doi: 10.1152/ajpcell.00281.2019. [PMID: 31390227]
  • Changjiang Lei, Shixing Wu, Chong Wen, Yuan Li, Ning Liu, Jianbin Huang, Lei Li, Meixia Fu, Jiani Liu. Zafirlukast attenuates advanced glycation end-products (AGEs)-induced degradation of articular extracellular matrix (ECM). International immunopharmacology. 2019 Mar; 68(?):68-73. doi: 10.1016/j.intimp.2018.12.056. [PMID: 30612086]
  • Joanne M Donkers, Benno Zehnder, Gerard J P van Westen, Mark J Kwakkenbos, Adriaan P IJzerman, Ronald P J Oude Elferink, Ulrich Beuers, Stephan Urban, Stan F J van de Graaf. Reduced hepatitis B and D viral entry using clinically applied drugs as novel inhibitors of the bile acid transporter NTCP. Scientific reports. 2017 11; 7(1):15307. doi: 10.1038/s41598-017-15338-0. [PMID: 29127322]
  • Evelien Gerits, Isolde Van der Massen, Katleen Vandamme, Kaat De Cremer, Katrijn De Brucker, Karin Thevissen, Bruno P A Cammue, Serge Beullens, Maarten Fauvart, Natalie Verstraeten, Jan Michiels. In vitro activity of the antiasthmatic drug zafirlukast against the oral pathogens Porphyromonas gingivalis and Streptococcus mutans. FEMS microbiology letters. 2017 01; 364(2):. doi: 10.1093/femsle/fnx005. [PMID: 28087617]
  • Hyun-Jee Lee, Young-Hoon Kim, Se-Hyung Kim, Choong-Min Lee, Ae-Yun Yang, Choon-Gon Jang, Seok-Yong Lee, Jung-Woo Bae, Chang-Ik Choi. Effects of CYP2C9 genetic polymorphisms on the pharmacokinetics of zafirlukast. Archives of pharmacal research. 2016 Jul; 39(7):1013-9. doi: 10.1007/s12272-016-0785-x. [PMID: 27377818]
  • Valérie Capra, Chiara Carnini, Maria Rosa Accomazzo, Antonio Di Gennaro, Marco Fiumicelli, Emanuele Borroni, Ivan Brivio, Carola Buccellati, Paolo Mangano, Silvia Carnevali, Gianenrico Rovati, Angelo Sala. Autocrine activity of cysteinyl leukotrienes in human vascular endothelial cells: Signaling through the CysLT₂ receptor. Prostaglandins & other lipid mediators. 2015 Jul; 120(?):115-25. doi: 10.1016/j.prostaglandins.2015.03.007. [PMID: 25839425]
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  • Tiina Karonen, Jouko Laitila, Mikko Niemi, Pertti J Neuvonen, Janne T Backman. Fluconazole but not the CYP3A4 inhibitor, itraconazole, increases zafirlukast plasma concentrations. European journal of clinical pharmacology. 2012 May; 68(5):681-8. doi: 10.1007/s00228-011-1158-5. [PMID: 22108774]
  • Susanna L Lundström, Jun Yang, Henrik J Källberg, Sarah Thunberg, Guro Gafvelin, Jesper Z Haeggström, Reidar Grönneberg, Johan Grunewald, Marianne van Hage, Bruce D Hammock, Anders Eklund, Åsa M Wheelock, Craig E Wheelock. Allergic asthmatics show divergent lipid mediator profiles from healthy controls both at baseline and following birch pollen provocation. PloS one. 2012; 7(3):e33780. doi: 10.1371/journal.pone.0033780. [PMID: 22438998]
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  • Amin Kanani, Robert Schellenberg, Richard Warrington. Urticaria and angioedema. Allergy, asthma, and clinical immunology : official journal of the Canadian Society of Allergy and Clinical Immunology. 2011 Nov; 7 Suppl 1(?):S9. doi: 10.1186/1710-1492-7-s1-s9. [PMID: 22165855]
  • Yasuto Kido, Pär Matsson, Kathleen M Giacomini. Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. Journal of medicinal chemistry. 2011 Jul; 54(13):4548-58. doi: 10.1021/jm2001629. [PMID: 21599003]
  • Tiina Karonen, Pertti J Neuvonen, Janne T Backman. The CYP2C8 inhibitor gemfibrozil does not affect the pharmacokinetics of zafirlukast. European journal of clinical pharmacology. 2011 Feb; 67(2):151-5. doi: 10.1007/s00228-010-0908-0. [PMID: 20931329]
  • Zeinab Mohamed Radwan, Gamal Abdel Nasser Yamamah, Hala Hamdy Shaaban, Azza Mohamed Omar Abdel-Rahman, Amany Abdel-Ghany Ismaeil, Elham Mohamed Mostafa. Effect of different monotherapies on serum nitric oxide and pulmonary functions in children with mild persistent asthma. Archives of medical science : AMS. 2010 Dec; 6(6):919-25. doi: 10.5114/aoms.2010.19302. [PMID: 22427767]
  • Amy E DeClue, Claire R Sharp, Rachael L Cohen, Elizabeth F Leverenz, Carol R Reinero. Cysteinyl-leukotriene receptor antagonism blunts the acute hypotensive response to endotoxin in cats. Journal of feline medicine and surgery. 2010 Oct; 12(10):754-9. doi: 10.1016/j.jfms.2010.05.012. [PMID: 20719552]
  • T Kezeli, N Gongadze, Z Chapichadze, K Bakuridze, K Chirakadze. Effect of combination of zafirlukast and quercetin on baroreflex sensitivity and endothelin production in rats with myocardial infarction. International journal of clinical pharmacology and therapeutics. 2010 May; 48(5):335-41. doi: 10.5414/cpp48335. [PMID: 20420790]
  • Upal Roy, Geetika Chakravarty, Kerstin Honer Zu Bentrup, Debasis Mondal. Montelukast is a potent and durable inhibitor of multidrug resistance protein 2-mediated efflux of taxol and saquinavir. Biological & pharmaceutical bulletin. 2009 Dec; 32(12):2002-9. doi: 10.1248/bpb.32.2002. [PMID: 19952419]
  • Sudha Yadav, A K Bajaj. Management of difficult urticaria. Indian journal of dermatology. 2009 Jul; 54(3):275-9. doi: 10.4103/0019-5154.55641. [PMID: 20161863]
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  • Gabriele Di Lorenzo, Alberto D'Alcamo, Manfredi Rizzo, Maria Stefania Leto-Barone, Claudia Lo Bianco, Vito Ditta, Donatella Politi, Francesco Castello, Ilenia Pepe, Gaetana Di Fede, Giovambattista Rini. Leukotriene receptor antagonists in monotherapy or in combination with antihistamines in the treatment of chronic urticaria: a systematic review. Journal of asthma and allergy. 2008 Dec; 2(?):9-16. doi: 10.2147/jaa.s3236. [PMID: 21437139]
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  • Tina Little, Bruce D Butler. Pharmacological intervention to the inflammatory response from decompression sickness in rats. Aviation, space, and environmental medicine. 2008 Feb; 79(2):87-93. doi: 10.3357/asem.2118.2008. [PMID: 18309904]
  • Incilay Süslü, Sacide Altinöz. A reversed-phase high-performance liquid chromatographic method for the determination of zafirlukast in pharmaceutical formulations and human plasma. Journal of AOAC International. 2006 Nov; 89(6):1557-64. doi: 10.1093/jaoac/89.6.1557. [PMID: 17225602]
  • Fumiaki Yamashita, Hisakazu Ohtani, Noriko Koyabu, Fumihiko Ushigome, Hiroki Satoh, Hideyasu Murakami, Takeshi Uchiumi, Takanori Nakamura, Michihiko Kuwano, Masayuki Tsujimoto, Yasufumi Sawada. Inhibitory effects of angiotensin II receptor antagonists and leukotriene receptor antagonists on the transport of human organic anion transporter 4. The Journal of pharmacy and pharmacology. 2006 Nov; 58(11):1499-505. doi: 10.1211/jpp.58.11.0011. [PMID: 17132213]
  • Tiina Jaakkola, Janne T Backman, Mikko Neuvonen, Mikko Niemi, Pertti J Neuvonen. Montelukast and zafirlukast do not affect the pharmacokinetics of the CYP2C8 substrate pioglitazone. European journal of clinical pharmacology. 2006 Jul; 62(7):503-9. doi: 10.1007/s00228-006-0136-9. [PMID: 16670899]
  • M Peters-Golden, M M Gleason, A Togias. Cysteinyl leukotrienes: multi-functional mediators in allergic rhinitis. Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology. 2006 Jun; 36(6):689-703. doi: 10.1111/j.1365-2222.2006.02498.x. [PMID: 16776669]
  • G Di Lorenzo, M L Pacor, P Mansueto, M Esposito-Pellitteri, V Ditta, C Lo Bianco, M S Leto-Barone, G Di Fede, G B Rini. Is there a role for antileukotrienes in urticaria?. Clinical and experimental dermatology. 2006 May; 31(3):327-34. doi: 10.1111/j.1365-2230.2006.02127.x. [PMID: 16681569]
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  • David Goldmeier, Peter Madden, Michael McKenna, Norbert Tamm. Treatment of category III A prostatitis with zafirlukast: a randomized controlled feasibility study. International journal of STD & AIDS. 2005 Mar; 16(3):196-200. doi: 10.1258/0956462053420239. [PMID: 15829018]
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