Lumiracoxib (BioDeep_00000033314)

   

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


2-{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetic acid

化学式: C15H13ClFNO2 (293.06188000000003)
中文名称: 罗美昔布
谱图信息: 最多检出来源 Homo sapiens(blood) 2.44%

分子结构信息

SMILES: CC1=CC(=C(C=C1)NC2=C(C=CC=C2Cl)F)CC(=O)O
InChI: InChI=1S/C15H13ClFNO2/c1-9-5-6-13(10(7-9)8-14(19)20)18-15-11(16)3-2-4-12(15)17/h2-7,18H,8H2,1H3,(H,19,20)

描述信息

Lumiracoxib is a COX-2 selective inhibitor non-steroidal anti-inflammatory drug. On August 11, 2007, Australias Therapeutic Goods Administration (TGA, the Australian equivalent of the FDA) cancelled the registration of lumiracoxib in Australia due to concerns that it may cause liver failure. New Zealand and Canada have also followed suit in recalling the drug.
M - Musculo-skeletal system > M01 - Antiinflammatory and antirheumatic products > M01A - Antiinflammatory and antirheumatic products, non-steroids > M01AH - Coxibs
D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors
D004791 - Enzyme Inhibitors > D016861 - Cyclooxygenase Inhibitors > D052246 - Cyclooxygenase 2 Inhibitors
C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent > C2198 - Nonnarcotic Analgesic
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics
C471 - Enzyme Inhibitor > C1323 - Cyclooxygenase Inhibitor
D000893 - Anti-Inflammatory Agents

同义名列表

9 个代谢物同义名

2-{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetic acid; 2-((2-Chloro-6-fluorophenyl)amino)-5-methylbenzeneacetic acid; 2-((2-Chloro-6-fluorophenyl)amino)-5-methylbenzeneacetate; Lumiracoxibum; Lumiracoxib; COX 189; COX-189; Prexige; COX189



数据库引用编号

8 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

  • Jun Sun, Lei Zhang, Lingchun Zhang, Qingwang Liu. A validated UHPLC-MS/MS method for simultaneous determination of lumiracoxib and its hydroxylation and acyl glucuronidation metabolites in rat plasma: Application to a pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2021 Jul; 201(?):114105. doi: 10.1016/j.jpba.2021.114105. [PMID: 33991809]
  • Weijie Jiao, Xu Zhao, Guiyue Wu, Xiangyun Zhang, Hong Wu, Yinglin Cui. Bioactivation of lumiracoxib in human liver microsomes: Formation of GSH- and amino adducts through acyl glucuronide. Drug testing and analysis. 2020 Jun; 12(6):827-835. doi: 10.1002/dta.2777. [PMID: 32043805]
  • A P Dickie, C E Wilson, K Schreiter, R Wehr, E M Wilson, J Bial, N Scheer, I D Wilson, R J Riley. The pharmacokinetics and metabolism of lumiracoxib in chimeric humanized and murinized FRG mice. Biochemical pharmacology. 2017 07; 135(?):139-150. doi: 10.1016/j.bcp.2017.03.015. [PMID: 28351678]
  • Anthony P Dickie, Claire E Wilson, Kay Schreiter, Roland Wehr, Ian D Wilson, Rob Riley. Lumiracoxib metabolism in male C57bl/6J mice: characterisation of novel in vivo metabolites. Xenobiotica; the fate of foreign compounds in biological systems. 2017 Jun; 47(6):538-546. doi: 10.1080/00498254.2016.1206239. [PMID: 27430634]
  • Shohei Takai, Shingo Oda, Koichi Tsuneyama, Tatsuki Fukami, Miki Nakajima, Tsuyoshi Yokoi. Establishment of a mouse model for amiodarone-induced liver injury and analyses of its hepatotoxic mechanism. Journal of applied toxicology : JAT. 2016 Jan; 36(1):35-47. doi: 10.1002/jat.3141. [PMID: 25900201]
  • Lisa Felden, Carmen Walter, Carlo Angioni, Yannick Schreiber, Nils von Hentig, Nerea Ferreiros, Gerd Geisslinger, Jörn Lötsch. Similar maximum systemic but not local cyclooxygenase-2 inhibition by 50 mg lumiracoxib and 90 mg etoricoxib: a randomized controlled trial in healthy subjects. Pharmaceutical research. 2014 Jul; 31(7):1813-22. doi: 10.1007/s11095-013-1285-z. [PMID: 24469906]
  • 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]
  • Hiroaki Honjo, Yuichi Uwai, Tomohiro Nabekura. Effect of selective cyclooxygenase-2 inhibitor lumiracoxib on phenolsulfonphthalein disposition in rats. Drug metabolism and drug interactions. 2014; 29(3):203-6. doi: 10.1515/dmdi-2014-0008. [PMID: 24870608]
  • Andy J Liedtke, Brenda C Crews, Cristina M Daniel, Anna L Blobaum, Philip J Kingsley, Kebreab Ghebreselasie, Lawrence J Marnett. Cyclooxygenase-1-selective inhibitors based on the (E)-2'-des-methyl-sulindac sulfide scaffold. Journal of medicinal chemistry. 2012 Mar; 55(5):2287-300. doi: 10.1021/jm201528b. [PMID: 22263894]
  • Kang Nyeong Lee, Oh Young Lee, Myung-Gyu Choi, Seok Reyol Choi, Dong Ho Lee, Yong Chan Lee, Tae Nyeun Kim, Suck Chei Choi, Jong Sun Rew, Sang-Yong Seol. Prevention of NSAID-associated gastroduodenal injury in healthy volunteers-a randomized, double-blind, multicenter study comparing DA-9601 with misoprostol. Journal of Korean medical science. 2011 Aug; 26(8):1074-80. doi: 10.3346/jkms.2011.26.8.1074. [PMID: 21860559]
  • Anke Olliges, Stefanie Wimmer, Rolf M Nüsing. Defects in mouse nephrogenesis induced by selective and non-selective cyclooxygenase-2 inhibitors. British journal of pharmacology. 2011 Jul; 163(5):927-36. doi: 10.1111/j.1476-5381.2011.01313.x. [PMID: 21391980]
  • Juergen Kindla, Fabian Müller, Maren Mieth, Martin F Fromm, Jörg König. Influence of non-steroidal anti-inflammatory drugs on organic anion transporting polypeptide (OATP) 1B1- and OATP1B3-mediated drug transport. Drug metabolism and disposition: the biological fate of chemicals. 2011 Jun; 39(6):1047-53. doi: 10.1124/dmd.110.037622. [PMID: 21389119]
  • Charles Faselis, Michael Doumas, Vasilios Papademetriou. Common secondary causes of resistant hypertension and rational for treatment. International journal of hypertension. 2011 Mar; 2011(?):236239. doi: 10.4061/2011/236239. [PMID: 21423678]
  • Włodzimierz Matysiak, Barbara Jodłowska-Jedrych. Does administration of non-steroidal anti-inflammatory drug determine morphological changes in adrenal cortex: ultrastructural studies. Protoplasma. 2010 Oct; 246(1-4):109-18. doi: 10.1007/s00709-010-0194-9. [PMID: 20721677]
  • Tailane Sant'Anna Moreira, Valéria Pereira de Sousa, Maria Bernadete Riemma Pierre. A novel transdermal delivery system for the anti-inflammatory lumiracoxib: influence of oleic acid on in vitro percutaneous absorption and in vivo potential cutaneous irritation. AAPS PharmSciTech. 2010 Jun; 11(2):621-9. doi: 10.1208/s12249-010-9420-1. [PMID: 20373151]
  • Linda Swedin, Russ Ellis, Theresa Neimert-Andersson, Ake Ryrfeldt, Gunnar Nilsson, Mark Inman, Sven-Erik Dahlén, Mikael Adner. Prostaglandin modulation of airway inflammation and hyperresponsiveness in mice sensitized without adjuvant. Prostaglandins & other lipid mediators. 2010 Jun; 92(1-4):44-53. doi: 10.1016/j.prostaglandins.2010.02.004. [PMID: 20214998]
  • Maria Leila Cardoso, Caroline A Xavier, Maria B Emilia Bezerra, Almino O Afonso Paiva, Maria F Goretti Carvalho, Norma M B Benevides, Francisco A C Rocha, Edda Lisboa Leite. Assessment of zymosan-induced leukocyte influx in a rat model using sulfated polysaccharides. Planta medica. 2010 Feb; 76(2):113-9. doi: 10.1055/s-0029-1186003. [PMID: 19653146]
  • Bertold Renner, Josef Zacher, Asokumar Buvanendran, Gerrit Walter, Jochen Strauss, Kay Brune. Absorption and distribution of etoricoxib in plasma, CSF, and wound tissue in patients following hip surgery--a pilot study. Naunyn-Schmiedeberg's archives of pharmacology. 2010 Feb; 381(2):127-36. doi: 10.1007/s00210-009-0482-0. [PMID: 20052461]
  • Tailane Sant'Anna Moreira, Valéria Pereira de Sousa, Maria Bernadete Riemma Pierre. Influence of oleic acid on the rheology and in vitro release of lumiracoxib from poloxamer gels. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2010; 13(2):286-302. doi: 10.18433/j34880. [PMID: 20816013]
  • D A Vásquez-Bahena, U E Salazar-Morales, M I Ortiz, G Castañeda-Hernández, Iñaki F Trocóniz. Pharmacokinetic-pharmacodynamic modelling of the analgesic effects of lumiracoxib, a selective inhibitor of cyclooxygenase-2, in rats. British journal of pharmacology. 2010 Jan; 159(1):176-87. doi: 10.1111/j.1476-5381.2009.00508.x. [PMID: 19958362]
  • Thorsten J Maier, Susanne Schiffmann, Ivonne Wobst, Kerstin Birod, Carlo Angioni, Marika Hoffmann, Jakob J Lopez, Clemens Glaubitz, Dieter Steinhilber, Gerd Geisslinger, Sabine Grösch. Cellular membranes function as a storage compartment for celecoxib. Journal of molecular medicine (Berlin, Germany). 2009 Oct; 87(10):981-93. doi: 10.1007/s00109-009-0506-8. [PMID: 19641861]
  • Loren Laine, William B White, Alaa Rostom, Marc Hochberg. COX-2 selective inhibitors in the treatment of osteoarthritis. Seminars in arthritis and rheumatism. 2008 Dec; 38(3):165-87. doi: 10.1016/j.semarthrit.2007.10.004. [PMID: 18177922]
  • Kirstin Stricker, Sue Yu, Gerhard Krammer. A 6-week, multicentre, randomised, double-blind, double-dummy, active-controlled, clinical safety study of lumiracoxib and rofecoxib in osteoarthritis patients. BMC musculoskeletal disorders. 2008 Sep; 9(?):118. doi: 10.1186/1471-2474-9-118. [PMID: 18778469]
  • I Moodley. Review of the cardiovascular safety of COXIBs compared to NSAIDS. Cardiovascular journal of Africa. 2008 Mar; 19(2):102-7. doi: . [PMID: 18516356]
  • Shaojun Shi, Ulrich Klotz. Clinical use and pharmacological properties of selective COX-2 inhibitors. European journal of clinical pharmacology. 2008 Mar; 64(3):233-52. doi: 10.1007/s00228-007-0400-7. [PMID: 17999057]
  • S A Holanda Pinto, L M S Pinto, G M A Cunha, M H Chaves, F A Santos, V S Rao. Anti-inflammatory effect of alpha, beta-Amyrin, a pentacyclic triterpene from Protium heptaphyllum in rat model of acute periodontitis. Inflammopharmacology. 2008 Feb; 16(1):48-52. doi: 10.1007/s10787-007-1609-x. [PMID: 18046512]
  • Bernard Bannwarth, Francis Bérenbaum. Lumiracoxib in the management of osteoarthritis and acute pain. Expert opinion on pharmacotherapy. 2007 Jul; 8(10):1551-64. doi: 10.1517/14656566.8.10.1551. [PMID: 17661736]
  • J W J Bijlsma, W F Lems, M A F J van de Laar. [Further definition of the role of COX-2 inhibitors and NSAIDs in patients with nociceptive pain]. Nederlands tijdschrift voor geneeskunde. 2007 Apr; 151(14):795-8. doi: . [PMID: 17469317]
  • Asokumar Buvanendran, Robert Barkin. Lumiracoxib. Drugs of today (Barcelona, Spain : 1998). 2007 Mar; 43(3):137-47. doi: 10.1358/dot.2007.43.3.1062673. [PMID: 17380211]
  • Marta L Capone, Stefania Tacconelli, Luigia Di Francesco, Andrea Sacchetti, Maria G Sciulli, Paola Patrignani. Pharmacodynamic of cyclooxygenase inhibitors in humans. Prostaglandins & other lipid mediators. 2007 Jan; 82(1-4):85-94. doi: 10.1016/j.prostaglandins.2006.05.019. [PMID: 17164136]
  • R Andrew Moore, Sheena Derry, Ceri J Phillips, Henry J McQuay. Nonsteroidal anti-inflammatory drugs (NSAIDs), cyxlooxygenase-2 selective inhibitors (coxibs) and gastrointestinal harm: review of clinical trials and clinical practice. BMC musculoskeletal disorders. 2006 Oct; 7(?):79. doi: 10.1186/1471-2474-7-79. [PMID: 17054784]
  • Olga Cheremina, Kay Brune, Burkhard Hinz. A validated high-performance liquid chromatographic assay for determination of lumiracoxib in human plasma. Biomedical chromatography : BMC. 2006 Oct; 20(10):1033-7. doi: 10.1002/bmc.633. [PMID: 16602135]
  • Jean-Pierre Valat, Gilbert Deray, François Héloire. [Are there any differences in the cardiovascular tolerance between classical NSAIDs and coxibs?]. Presse medicale (Paris, France : 1983). 2006 Sep; 35 Suppl 1(?):25-34. doi: 10.1016/s0755-4982(06)74937-5. [PMID: 17870550]
  • Timothy D Warner, Ivana Vojnovic, David Bishop-Bailey, Jane A Mitchell. Influence of plasma protein on the potencies of inhibitors of cyclooxygenase-1 and -2. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2006 Mar; 20(3):542-4. doi: 10.1096/fj.05-4434fje. [PMID: 16403783]
  • J Jermany, J Branson, R Schmouder, M Guillaume, C Rordorf. Lumiracoxib does not affect the ex vivo antiplatelet aggregation activity of low-dose aspirin in healthy subjects. Journal of clinical pharmacology. 2005 Oct; 45(10):1172-8. doi: 10.1177/0091270005280377. [PMID: 16172182]
  • Elliot V Hersh, Edward T Lally, Paul A Moore. Update on cyclooxygenase inhibitors: has a third COX isoform entered the fray?. Current medical research and opinion. 2005 Aug; 21(8):1217-26. doi: 10.1185/030079905x56367. [PMID: 16083531]
  • Ronald E Esser, Rocca Miserendino-Molteni, Michele Sharr, Xiaoli Zhang, Wilma Porter, Luis Ramos, Jeffrey A Cramer, Shumin Zhuang, Anna Georgieva, Wieslawa Maniara. Pharmacodynamic behaviour of the selective cyclooxygenase-2 inhibitor lumiracoxib in the lipopolysaccharide-stimulated rat air pouch model. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2005 May; 25(1):25-30. doi: 10.1016/j.ejps.2005.01.014. [PMID: 15854797]
  • Bernard Bannwarth, Francis Berenbaum. Clinical pharmacology of lumiracoxib, a second-generation cyclooxygenase 2 selective inhibitor. Expert opinion on investigational drugs. 2005 Apr; 14(4):521-33. doi: 10.1517/13543784.14.4.521. [PMID: 15882125]
  • Ronald Esser, Carol Berry, Zhengming Du, Janet Dawson, Alyson Fox, Roger A Fujimoto, William Haston, Earl F Kimble, Julie Koehler, Jane Peppard, Elizabeth Quadros, Joseph Quintavalla, Karen Toscano, Laszlo Urban, John van Duzer, Xiaoli Zhang, Siyuan Zhou, Paul J Marshall. Preclinical pharmacology of lumiracoxib: a novel selective inhibitor of cyclooxygenase-2. British journal of pharmacology. 2005 Feb; 144(4):538-50. doi: 10.1038/sj.bjp.0706078. [PMID: 15655513]
  • Christiane M Rordorf, Les Choi, Paul Marshall, James B Mangold. Clinical pharmacology of lumiracoxib: a selective cyclo-oxygenase-2 inhibitor. Clinical pharmacokinetics. 2005; 44(12):1247-66. doi: 10.2165/00003088-200544120-00004. [PMID: 16372823]
  • Stefan N Hartmann, Christiane M Rordorf, Slavica Milosavljev, Janice M Branson, Gérard H Chales, Robert R Juvin, Pierre Lafforgue, Jean Marie Le Parc, Christian G Tavernier, Olivier C Meyer. Lumiracoxib does not affect methotrexate pharmacokinetics in rheumatoid arthritis patients. The Annals of pharmacotherapy. 2004 Oct; 38(10):1582-7. doi: 10.1345/aph.1e044. [PMID: 15340127]
  • J Kalbag, C-M Yeh, S Milosavljev, K Lasseter, S Oberstein, C Rordorf. No influence of moderate hepatic impairment on the pharmacokinetics of lumiracoxib, an oral COX-2 selective inhibitor. Pharmacological research. 2004 Aug; 50(2):181-6. doi: 10.1016/j.phrs.2004.03.002. [PMID: 15177307]
  • Jyoti Kalbag, Cheryl Elder, Graham Scott, Yibin Wang, Slavica Milosavljev, Philipp Leese, Jacque Caldwell, Christiane Rordorf. Concomitant administration of lumiracoxib and a triphasic oral contraceptive does not affect contraceptive activity or pharmacokinetic profile. Journal of clinical pharmacology. 2004 Jun; 44(6):646-54. doi: 10.1177/0091270004265363. [PMID: 15145973]
  • James B Mangold, Helen Gu, Lolita C Rodriguez, Johanne Bonner, Janet Dickson, Christiane Rordorf. Pharmacokinetics and metabolism of lumiracoxib in healthy male subjects. Drug metabolism and disposition: the biological fate of chemicals. 2004 May; 32(5):566-71. doi: 10.1124/dmd.32.5.566. [PMID: 15100180]
  • Timothy D Warner, Jane A Mitchell. Cyclooxygenases: new forms, new inhibitors, and lessons from the clinic. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2004 May; 18(7):790-804. doi: 10.1096/fj.03-0645rev. [PMID: 15117884]
  • Jean-Yves Jouzeau, Mikaël Daouphars, Alexandre Benani, Patrick Netter. [Pharmacology and classification of cyclooxygenase inhibitors]. Gastroenterologie clinique et biologique. 2004 Apr; 28 Spec No 3(?):C7-17. doi: 10.1016/s0399-8320(04)95274-8. [PMID: 15366670]
  • Clare Atherton, John Jones, Brian McKaig, James Bebb, Rob Cunliffe, Jake Burdsall, Joanne Brough, Diane Stevenson, Johanne Bonner, Christiane Rordorf, Graham Scott, Janice Branson, Christopher J Hawkey. Pharmacology and gastrointestinal safety of lumiracoxib, a novel cyclooxygenase-2 selective inhibitor: An integrated study. Clinical gastroenterology and hepatology : the official clinical practice journal of the American Gastroenterological Association. 2004 Feb; 2(2):113-20. doi: 10.1016/s1542-3565(03)00318-5. [PMID: 15017615]
  • Katherine A Lyseng-Williamson, Monique P Curran. Lumiracoxib. Drugs. 2004; 64(19):2237-46; discussion 2247. doi: 10.2165/00003495-200464190-00008. [PMID: 15456339]
  • Graham Scott, Christine Vinluan Reynolds, Slavica Milosavljev, Wayne Langholff, Magdy Shenouda, Christiane Rordorf. Lack of effect of omeprazole or of an aluminium hydroxide/magnesium hydroxide antacid on the pharmacokinetics of lumiracoxib. Clinical pharmacokinetics. 2004; 43(5):341-8. doi: 10.2165/00003088-200443050-00006. [PMID: 15080766]
  • Graham Scott, Christiane Rordorf, Christine Reynolds, Jyoti Kalbag, Michael Looby, Slavica Milosavljev, Margaret Weaver, John P Huff, Dennis A Ruff. Pharmacokinetics of lumiracoxib in plasma and synovial fluid. Clinical pharmacokinetics. 2004; 43(7):467-78. doi: 10.2165/00003088-200443070-00003. [PMID: 15139795]
  • C Rordorf, N Kellett, S Mair, M Ford, S Milosavljev, J Branson, G Scott. Gastroduodenal tolerability of lumiracoxib vs placebo and naproxen: a pilot endoscopic study in healthy male subjects. Alimentary pharmacology & therapeutics. 2003 Sep; 18(5):533-41. doi: 10.1046/j.1365-2036.2003.01691.x. [PMID: 12950426]
  • M Bayés, X Rabasseda, J R Prous. Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology. 2003 Jul; 25(6):483-506. doi: . [PMID: 12949633]