Eprosartan (BioDeep_00000001540)

 

Secondary id: BioDeep_00001868003

human metabolite blood metabolite


代谢物信息卡片


4-({2-butyl-5-[(1E)-2-carboxy-2-(thiophen-2-ylmethyl)eth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid

化学式: C23H24N2O4S (424.14567040000003)
中文名称: 依普罗沙坦
谱图信息: 最多检出来源 Viridiplantae(plant) 1.96%

分子结构信息

SMILES: CCCCC1=NC=C(N1CC2=CC=C(C=C2)C(=O)O)/C=C(\CC3=CC=CS3)/C(=O)O
InChI: InChI=1S/C23H24N2O4S/c1-2-3-6-21-24-14-19(12-18(23(28)29)13-20-5-4-11-30-20)25(21)15-16-7-9-17(10-8-16)22(26)27/h4-5,7-12,14H,2-3,6,13,15H2,1H3,(H,26,27)(H,28,29)/b18-12+

描述信息

Eprosartan is an angiotensin II receptor antagonist used for the treatment of high blood pressure. It acts on the renin-angiotensin system in two ways to decrease total peripheral resistance. First, it blocks the binding of angiotensin II to AT1 receptors in vascular smooth muscle, causing vascular dilatation. Second, it inhibits sympathetic norepinephrine production, further reducing blood pressure.
C - Cardiovascular system > C09 - Agents acting on the renin-angiotensin system > C09C - Angiotensin ii receptor blockers (arbs), plain > C09CA - Angiotensin ii receptor blockers (arbs), plain
C78274 - Agent Affecting Cardiovascular System > C270 - Antihypertensive Agent > C66930 - Angiotensin II Receptor Antagonist
D057911 - Angiotensin Receptor Antagonists > D057912 - Angiotensin II Type 2 Receptor Blockers
COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials
D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents
CONFIDENCE standard compound; EAWAG_UCHEM_ID 2776
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
Eprosartan (SKF-108566J free base) is a selective, competitive, nonpeptid and orally active angiotensin II receptor antagonist, used as an antihypertensive. Eprosartan binds angiotensin II receptor with IC50s of 9.2 nM and 3.9 nM in rat and human adrenal cortical membranes, respectively [1].

同义名列表

16 个代谢物同义名

4-({2-butyl-5-[(1E)-2-carboxy-2-(thiophen-2-ylmethyl)eth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid; (e)-Alpha{[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazole-5-yl]methylene}-2-thiopheneproprionic acid; (e)-3-[2-N-Butyl-1-{(4-carboxyphenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoic acid; (e)-Alpha{[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazole-5-yl]methylene}-2-thiopheneproprionate; (e)-3-[2-N-Butyl-1-{(4-carboxyphenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoate; (e)-2-Butyl-1-(p-carboxybenzyl)-alpha-2-thenylimidazole-5-acrylic acid; (e)-2-Butyl-1-(p-carboxybenzyl)-alpha-2-thenylimidazole-5-acrylate; (e)-2-Butyl-1-(p-carboxybenzyl)-a-2-thenylimidazole-5-acrylic acid; (e)-2-Butyl-1-(p-carboxybenzyl)-α-2-thenylimidazole-5-acrylic acid; (e)-2-Butyl-1-(p-carboxybenzyl)-a-2-thenylimidazole-5-acrylate; (e)-2-Butyl-1-(p-carboxybenzyl)-α-2-thenylimidazole-5-acrylate; Teveten; SK&F108566; SK And F 108566; Eprosartan; Teveten; SKF-108566J (free base)



数据库引用编号

46 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。

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

  • Anna Masajtis-Zagajewska, Jacek Majer, Michał Nowicki. Losartan and Eprosartan Induce a Similar Effect on the Acute Rise in Serum Uric Acid Concentration after an Oral Fructose Load in Patients with Metabolic Syndrome. Journal of the renin-angiotensin-aldosterone system : JRAAS. 2021; 2021(?):2214978. doi: 10.1155/2021/2214978. [PMID: 34527078]
  • G N Leonova, O S Maistrovskaya, V A Lubova. Molecular and Genetic Bases of Inhibition of Tick-Borne Encephalitis Virus Replication by Eprosartan and Ribavirin. Bulletin of experimental biology and medicine. 2020 Nov; 170(1):53-57. doi: 10.1007/s10517-020-05003-4. [PMID: 33222083]
  • Daan J L van Twist, Alfons J H M Houben, Peter W de Leeuw, Abraham A Kroon. Acute eprosartan-induced intrarenal vasodilation in hypertensive humans is not influenced by dietary sodium intake or angiotensin II co-infusion. Journal of hypertension. 2016 08; 34(8):1607-14. doi: 10.1097/hjh.0000000000000974. [PMID: 27214088]
  • Mohamed A Morsy, Gehan H Heeba, Magda E Mahmoud. Ameliorative effect of eprosartan on high-fat diet/streptozotocin-induced early diabetic nephropathy in rats. European journal of pharmacology. 2015 Mar; 750(?):90-7. doi: 10.1016/j.ejphar.2015.01.027. [PMID: 25625658]
  • Pengyuan Sun, Changyuan Wang, Qi Liu, Qiang Meng, Aijie Zhang, Xiaokui Huo, Huijun Sun, Kexin Liu. OATP and MRP2-mediated hepatic uptake and biliary excretion of eprosartan in rat and human. Pharmacological reports : PR. 2014 Apr; 66(2):311-9. doi: 10.1016/j.pharep.2014.02.013. [PMID: 24911086]
  • Petra C van Rijn-Bikker, Oliver Ackaert, Nelleke Snelder, Reinier M van Hest, Bart A Ploeger, Richard P Koopmans, Ron A A Mathôt. Pharmacokinetic-pharmacodynamic modeling of the antihypertensive effect of eprosartan in Black and White hypertensive patients. Clinical pharmacokinetics. 2013 Sep; 52(9):793-803. doi: 10.1007/s40262-013-0073-6. [PMID: 23696281]
  • V V Kaliuzhin, O F Sibireva, O I Urazova, L M Tkalich, L I Zibnitskaia, E V Kaliuzhina, É A Sazonov, V Iu Grankina. [Effect of eprosartan on the hemostatic system in patients with chronic kidney disease associated with hereditary thrombophilia]. Terapevticheskii arkhiv. 2013; 85(9):77-81. doi: . [PMID: 24261234]
  • Suzan Willemsen, Jasper W L Hartog, M Rebecca Heiner-Fokkema, Dirk J van Veldhuisen, Adriaan A Voors. Advanced glycation end-products, a pathophysiological pathway in the cardiorenal syndrome. Heart failure reviews. 2012 Mar; 17(2):221-8. doi: 10.1007/s10741-010-9225-z. [PMID: 21259070]
  • C V Musa, A Mancini, A Alfieri, G Labruna, G Valerio, A Franzese, F Pasanisi, M R Licenziati, L Sacchetti, P Buono. Four novel UCP3 gene variants associated with childhood obesity: effect on fatty acid oxidation and on prevention of triglyceride storage. International journal of obesity (2005). 2012 Feb; 36(2):207-17. doi: 10.1038/ijo.2011.81. [PMID: 21544083]
  • Massimo Volpe, Carmine Savoia. New treatment options in the management of hypertension: appraising the potential role of azilsartan medoxomil. Integrated blood pressure control. 2012; 5(?):19-25. doi: 10.2147/ibpc.s13784. [PMID: 22457601]
  • Giuseppe Derosa, Pamela Maffioli. Nifedipine and telmisartan for the treatment of hypertension: the TALENT study. Expert review of cardiovascular therapy. 2011 Dec; 9(12):1499-503. doi: 10.1586/erc.11.155. [PMID: 22103868]
  • Isis T Silva, Ana P Q Mello, Nágila R T Damasceno. Antioxidant and inflammatory aspects of lipoprotein-associated phospholipase A₂ (Lp-PLA₂): a review. Lipids in health and disease. 2011 Sep; 10(?):170. doi: 10.1186/1476-511x-10-170. [PMID: 21955667]
  • Henrik Vase, Thomas G Lauridsen, Carolina C Graffe, Erling B Pedersen. The effect of eprosartan on reflex sympathetic activation in sodium restricted patients with essential hypertension. Journal of the American Society of Hypertension : JASH. 2011 Sep; 5(5):385-94. doi: 10.1016/j.jash.2011.03.007. [PMID: 21640689]
  • Maribel Reyes, Leslie Z Benet. Effects of uremic toxins on transport and metabolism of different biopharmaceutics drug disposition classification system xenobiotics. Journal of pharmaceutical sciences. 2011 Sep; 100(9):3831-42. doi: 10.1002/jps.22640. [PMID: 21618544]
  • Su-Jin Oh, Won-Chul Ha, Jee-In Lee, Tae-Seo Sohn, Ji-Hyun Kim, Jung-Min Lee, Sang-Ah Chang, Oak-Kee Hong, Hyun-Shik Son. Angiotensin II Inhibits Insulin Binding to Endothelial Cells. Diabetes & metabolism journal. 2011 Jun; 35(3):243-7. doi: 10.4093/dmj.2011.35.3.243. [PMID: 21785744]
  • Fathalla Belal, Amina M El-Brashy, Nahed El-Enany, Manar M Tolba. Liquid chromatographic method for the simultaneous determination of eprosartan and hydrochlorothiazide in tablets and human plasma. Journal of AOAC International. 2011 May; 94(3):823-32. doi: . [PMID: 21797010]
  • Linda Ferrington, J Scott Miners, Laura E Palmer, Susan M Bond, Joanne E Povey, Paul At Kelly, Seth Love, Karen J Horsburgh, Patrick G Kehoe. Angiotensin II-inhibiting drugs have no effect on intraneuronal Aβ or oligomeric Aβ levels in a triple transgenic mouse model of Alzheimer's disease. American journal of translational research. 2011 Feb; 3(2):197-208. doi: . [PMID: 21416061]
  • Masaki Mogi, Masatsugu Horiuchi. Clinical Interaction between Brain and Kidney in Small Vessel Disease. Cardiology research and practice. 2011 Jan; 2011(?):306189. doi: 10.4061/2011/306189. [PMID: 21274446]
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  • Jasper W L Hartog, Ruud M van de Wal, Casper G Schalkwijk, Toshio Miyata, Wybren Jaarsma, H W Thijs Plokker, Leen M van Wijk, Andries J Smit, Dirk J van Veldhuisen, Adriaan A Voors. Advanced glycation end-products, anti-hypertensive treatment and diastolic function in patients with hypertension and diastolic dysfunction. European journal of heart failure. 2010 Apr; 12(4):397-403. doi: 10.1093/eurjhf/hfq001. [PMID: 20154337]
  • Koichi Yamamoto, Mitsuru Ohishi, Christopher Ho, Theodore W Kurtz, Hiromi Rakugi. Telmisartan-induced inhibition of vascular cell proliferation beyond angiotensin receptor blockade and peroxisome proliferator-activated receptor-gamma activation. Hypertension (Dallas, Tex. : 1979). 2009 Dec; 54(6):1353-9. doi: 10.1161/hypertensionaha.109.138750. [PMID: 19822796]
  • R Fogari, A Zoppi, I Ferrari, A Mugellini, P Preti, P Lazzari, G Derosa. Comparative effects of telmisartan and eprosartan on insulin sensitivity in the treatment of overweight hypertensive patients. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 2009 Dec; 41(12):893-8. doi: 10.1055/s-0029-1237359. [PMID: 19708000]
  • Manthena V S Varma, Bo Feng, R Scott Obach, Matthew D Troutman, Jonathan Chupka, Howard R Miller, Ayman El-Kattan. Physicochemical determinants of human renal clearance. Journal of medicinal chemistry. 2009 Aug; 52(15):4844-52. doi: 10.1021/jm900403j. [PMID: 19445515]
  • Irit Rubinstein, Zaid Abassi, Felix Milman, Elena Ovcharenko, Rymond Coleman, Joseph Winaver, Ori S Better. Hyperbaric oxygen treatment improves GFR in rats with ischaemia/reperfusion renal injury: a possible role for the antioxidant/oxidant balance in the ischaemic kidney. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2009 Feb; 24(2):428-36. doi: 10.1093/ndt/gfn511. [PMID: 18799609]
  • Greg L Plosker. Eprosartan: a review of its use in hypertension. Drugs. 2009; 69(17):2477-99. doi: 10.2165/11203980-000000000-00000. [PMID: 19911859]
  • P J Blankestijn, H Rupp. Clinical profile of eprosartan: a different angiotensin II receptor blocker. Cardiovascular & hematological agents in medicinal chemistry. 2008 Oct; 6(4):253-7. doi: 10.2174/187152508785909500. [PMID: 18855637]
  • R Scott Obach, Franco Lombardo, Nigel J Waters. Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. Drug metabolism and disposition: the biological fate of chemicals. 2008 Jul; 36(7):1385-405. doi: 10.1124/dmd.108.020479. [PMID: 18426954]
  • Henrik Vase, Thomas G Lauridsen, Jesper N Bech, Erling B Pedersen. Eprosartan modulates the reflex activation of the sympathetic nervous system in sodium restricted healthy humans. British journal of clinical pharmacology. 2008 Jun; 65(6):822-32. doi: 10.1111/j.1365-2125.2008.03149.x. [PMID: 18341678]
  • Stephen C Benson, Rumiko Iguchi, Christopher I Ho, Koichi Yamamoto, Theodore W Kurtz. Inhibition of cardiovascular cell proliferation by angiotensin receptor blockers: are all molecules the same?. Journal of hypertension. 2008 May; 26(5):973-80. doi: 10.1097/hjh.0b013e3282f56ba5. [PMID: 18398340]
  • Nerea Ferreirós, Gorka Iriarte, Rosa María Alonso, Rosa María Jiménez, Eduardo Ortíz. Separation and quantitation of several angiotensin II receptor antagonist drugs in human urine by a SPE-HPLC-DAD method. Journal of separation science. 2008 Mar; 31(4):667-76. doi: 10.1002/jssc.200700442. [PMID: 18307163]
  • V B Simonenko, I N Medvedev, T A Kumova. [Effect of eprosartan on thrombocytes aggregative capacity in patients with arterial hypertension and metabolic syndrome]. Klinicheskaia meditsina. 2008; 86(4):19-21. doi: NULL. [PMID: 18494280]
  • Nerea Ferreirós, Sebastian Dresen, Rosa María Alonso, Wolfgang Weinmann. Validated quantitation of angiotensin II receptor antagonists (ARA-II) in human plasma by liquid-chromatography-tandem mass spectrometry using minimum sample clean-up and investigation of ion suppression. Therapeutic drug monitoring. 2007 Dec; 29(6):824-34. doi: 10.1097/ftd.0b013e31815d0f66. [PMID: 18043483]
  • C Venkata S Ram. Angiotensin blockade with eprosartan: vascular and functional implications. Current medical research and opinion. 2007 Nov; 23 Suppl 5(?):S5-11. doi: 10.1185/030079907x260700. [PMID: 18093408]
  • N Ferreirós, G Iriarte, R M Alonso, R M Jiménez. Development of a solid phase extraction procedure for HPLC-DAD determination of several angiotensin II receptor antagonists in human urine using mixture design. Talanta. 2007 Oct; 73(4):748-56. doi: 10.1016/j.talanta.2007.04.062. [PMID: 19073097]
  • H R Xu, W L Chen, X N Li, G Y Liu, N N Chu, C Yu. Pharmacokinetics and urinary excretion of eprosartan in Chinese healthy volunteers of different gender. Die Pharmazie. 2007 Oct; 62(10):782-4. doi: NULL. [PMID: 18236785]
  • Kavi J Littlewood, Wolfgang Greiner, Dominique Baum, York Zoellner. Adjunctive treatment with moxonidine versus nitrendipine for hypertensive patients with advanced renal failure: a cost-effectiveness analysis. BMC nephrology. 2007 Jul; 8(?):9. doi: 10.1186/1471-2369-8-9. [PMID: 17645811]
  • Xue-Ning Li, Hong-Rong Xu, Wei-Li Chen, Gang-Yi Liu, Nan-Nan Chu, Chen Yu. Determination of eprosartan in human plasma and urine by LC/MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 Jun; 853(1-2):47-53. doi: 10.1016/j.jchromb.2007.02.049. [PMID: 17409033]
  • Jutta Neumann, Gerry Ligtenberg, Inge H T Klein, Peter Boer, P Liam Oey, Hein A Koomans, Peter J Blankestijn. Sympathetic hyperactivity in hypertensive chronic kidney disease patients is reduced during standard treatment. Hypertension (Dallas, Tex. : 1979). 2007 Mar; 49(3):506-10. doi: 10.1161/01.hyp.0000256530.39695.a3. [PMID: 17224471]
  • Evangelos C Rizos, Athanasia Spyrou, Evangelos N Liberopoulos, Eleni C Papavasiliou, Vasilis Saougos, Alexandros D Tselepis, Moses Elisaf. Effects of eprosartan on serum metabolic parameters in patients with essential hypertension. The open cardiovascular medicine journal. 2007; 1(?):22-6. doi: 10.2174/1874192400701010022. [PMID: 18949087]
  • Fang Zhang, Brian E Lavan, Francine M Gregoire. Selective Modulators of PPAR-gamma Activity: Molecular Aspects Related to Obesity and Side-Effects. PPAR research. 2007; 2007(?):32696. doi: 10.1155/2007/32696. [PMID: 17389769]
  • David Fitchett. Clinical trial update: focus on the ONTARGET study. Vascular health and risk management. 2007; 3(6):901-8. doi: ". [PMID: 18200809]
  • N Ferreirós, G Iriarte, R M Alonso, R M Jiménez, E Ortíz. Validation of a solid phase extraction-high performance liquid chromatographic method for the determination of eprosartan in human plasma. Journal of chromatography. A. 2006 Jun; 1119(1-2):309-14. doi: 10.1016/j.chroma.2006.02.055. [PMID: 16542666]
  • N Ferreirós, G Iriarte, R M Alonso, R M Jiménez. MultiSimplex and experimental design as chemometric tools to optimize a SPE-HPLC-UV method for the determination of eprosartan in human plasma samples. Talanta. 2006 May; 69(3):747-56. doi: 10.1016/j.talanta.2005.11.036. [PMID: 18970633]
  • Henry Krum, Elisabeth Lambert, Emma Windebank, Duncan J Campbell, Murray Esler. Effect of angiotensin II receptor blockade on autonomic nervous system function in patients with essential hypertension. American journal of physiology. Heart and circulatory physiology. 2006 Apr; 290(4):H1706-12. doi: 10.1152/ajpheart.00885.2005. [PMID: 16284232]
  • A S Ametov, T Iu Demidova, S A Kosykh. [An AT-II blocker in patients with type II diabetes and arterial hypertension]. Klinicheskaia meditsina. 2006; 84(2):50-5. doi: . [PMID: 16613007]
  • Stella-Maria G Kyvelou, Gregory P Vyssoulis, Eva A Karpanou, Dionysios N Adamopoulos, Alexandra I Zervoudaki, Panagiota G Pietri, Christodoulos I Stefanadis. Effects of antihypertensive treatment with angiotensin II receptor blockers on lipid profile: an open multi-drug comparison trial. Hellenic journal of cardiology : HJC = Hellenike kardiologike epitheorese. 2006 Jan; 47(1):21-8. doi: NULL. [PMID: 16532712]
  • Tony Karram, Anan Abbasi, Shlomo Keidar, Eliahu Golomb, Irit Hochberg, Joseph Winaver, Aaron Hoffman, Zaid Abassi. Effects of spironolactone and eprosartan on cardiac remodeling and angiotensin-converting enzyme isoforms in rats with experimental heart failure. American journal of physiology. Heart and circulatory physiology. 2005 Oct; 289(4):H1351-8. doi: 10.1152/ajpheart.01186.2004. [PMID: 15894569]
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  • Ronald Clasen, Michael Schupp, Anna Foryst-Ludwig, Christiane Sprang, Markus Clemenz, Maxim Krikov, Christa Thöne-Reineke, Thomas Unger, Ulrich Kintscher. PPARgamma-activating angiotensin type-1 receptor blockers induce adiponectin. Hypertension (Dallas, Tex. : 1979). 2005 Jul; 46(1):137-43. doi: 10.1161/01.hyp.0000168046.19884.6a. [PMID: 15939809]
  • Jay P Garg, Renee Ellis, William J Elliott, Nahla Hasabou, Dave Chua, Glenn M Chertow, George L Bakris. Angiotensin receptor blockade and arterial compliance in chronic kidney disease: a pilot study. American journal of nephrology. 2005 Jul; 25(4):393-9. doi: 10.1159/000087211. [PMID: 16088080]
  • Cristiana Vitale, Giuseppe Mercuro, Carlotta Castiglioni, Alessandra Cornoldi, Arianna Tulli, Massimo Fini, Maurizio Volterrani, Giuseppe M C Rosano. Metabolic effect of telmisartan and losartan in hypertensive patients with metabolic syndrome. Cardiovascular diabetology. 2005 May; 4(?):6. doi: 10.1186/1475-2840-4-6. [PMID: 15892894]
  • Marina Christensen, Hans Ibsen, René Worck. Effect of eprosartan on catecholamines and peripheral haemodynamics in subjects with insulin-induced hypoglycaemia. Clinical science (London, England : 1979). 2005 Feb; 108(2):113-9. doi: 10.1042/cs20040094. [PMID: 15383007]
  • Duncan J Campbell, Henry Krum, Murray D Esler. Losartan increases bradykinin levels in hypertensive humans. Circulation. 2005 Jan; 111(3):315-20. doi: 10.1161/01.cir.0000153269.07762.3b. [PMID: 15655136]
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  • Jutta Neumann, Gerry Ligtenberg, Liam Oey, Hein A Koomans, Peter J Blankestijn. Moxonidine normalizes sympathetic hyperactivity in patients with eprosartan-treated chronic renal failure. Journal of the American Society of Nephrology : JASN. 2004 Nov; 15(11):2902-7. doi: 10.1097/01.asn.0000143471.10750.8c. [PMID: 15504943]
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