Etoricoxib, sold under the brand name Arcoxia, is a selective COX-2 inhibitor developed and commercialized by Merck. It is approved in 63 countries worldwide as of 2007, except the United States where the Food and Drug Administration sent a Non Approvable Letter to Merck and required them to provide additional data.
It was patented in 1996 and approved for medical use in 2002.
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InChI=1S/C18H15ClN2O2S/c1-12-3-4-14(10-20-12)18-17(9-15(19)11-21-18)13-5-7-16(8-6-13)24(2,22)23/h3-11H,1-2H3 |
MNJVRJDLRVPLFE-UHFFFAOYSA-N |
Cc1ccc(cn1)-c1ncc(Cl)cc1-c1ccc(cc1)S(C)(=O)=O |
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cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
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non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
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View more via ChEBI Ontology
5-chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-2,3'-bipyridine
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étoricoxib
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WHO MedNet
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etoricoxib
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WHO MedNet
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etoricoxib
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ChemIDplus
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etoricoxibum
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WHO MedNet
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5-chloro-2-(6-methylpyridin-3-yl)-3-(4-(methylsulfonyl)phenyl)pyridine
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ChEMBL
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5-Chloro-3-(4-methanesulfonyl-phenyl)-6'-methyl-[2,3']bipyridinyl
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ChEMBL
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5-chloro-6'-methyl-3-(p-(methylsulfonyl)phenyl)-2,3'-bipyridine
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ChemIDplus
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ETORICOXIB
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ChEMBL
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Etoricoxib
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KEGG COMPOUND
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L791456
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KEGG COMPOUND
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1113
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DrugCentral
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5CH
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PDBeChem
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C11718
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KEGG COMPOUND
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D03710
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KEGG DRUG
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DB01628
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DrugBank
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Etoricoxib
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Wikipedia
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LSM-5650
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LINCS
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View more database links |
202409-33-4
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CAS Registry Number
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KEGG COMPOUND
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202409-33-4
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CAS Registry Number
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ChemIDplus
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Khanapure SP, Augustyniak ME, Earl RA, Garvey DS, Letts LG, Martino AM, Murty MG, Schwalb DJ, Shumway MJ, Trocha AM, Young DV, Zemtseva IS, Janero DR (2005) 3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) phenyl ketone as a potent and orally active cyclooxygenase-2 selective inhibitor: synthesis and biological evaluation. Journal of medicinal chemistry 48, 3930-3934 (Source: ChEMBL) [PubMed:15916445] [show Abstract] Incorporation of a spacer group between the central scaffold and the aryl ring resulted in a new cyclooxygenase-2 (COX-2) selective inhibitor core structure, 3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) phenyl ketone (20), with COX-2 IC50 = 0.25 microM and COX-1 IC50 = 14 microM (human whole blood assay). Compound 20 was orally active in the rat air pouch model of inflammation, inhibiting white blood cell infiltration and COX-2-derived PG production. Our data support the identification of a novel COX-2 selective inhibitor core structure exemplified by 20. | Beswick P, Bingham S, Bountra C, Brown T, Browning K, Campbell I, Chessell I, Clayton N, Collins S, Corfield J, Guntrip S, Haslam C, Lambeth P, Lucas F, Mathews N, Murkit G, Naylor A, Pegg N, Pickup E, Player H, Price H, Stevens A, Stratton S, Wiseman J (2004) Identification of 2,3-diaryl-pyrazolo[1,5-b]pyridazines as potent and selective cyclooxygenase-2 inhibitors. Bioorganic & medicinal chemistry letters 14, 5445-5448 (Source: ChEMBL) [PubMed:15454242] [show Abstract] GW406381 (8), currently undergoing clinical evaluation for the treatment of inflammatory pain is a member of a novel series of 2,3-diaryl-pyrazolo[1,5-b]pyridazine based cyclooxygenase-2 (COX-2) inhibitors, which have been shown to be highly potent and selective. Several examples of the series, in addition to possessing favourable pharmacokinetic profiles and analgesic activity in vivo, have also demonstrated relatively high brain penetration in the rat compared with the clinically available compounds, which may ultimately prove beneficial in the treatment of pain. | Caturla F, Jiménez JM, Godessart N, Amat M, Cárdenas A, Soca L, Beleta J, Ryder H, Crespo MI (2004) Synthesis and biological evaluation of 2-phenylpyran-4-ones: a new class of orally active cyclooxygenase-2 inhibitors. Journal of medicinal chemistry 47, 3874-3886 (Source: ChEMBL) [PubMed:15239665] [show Abstract] A series of 2-phenylpyran-4-ones were prepared and evaluated for their ability to inhibit cyclooxygenase-2 (COX-2). Extensive structure-activity relationship work was carried out within this series, and a number of potent and selective COX-2 inhibitors were identified. Compounds having a p-methylsulfone group at the 2-phenyl ring showed the best COX-2 inhibitory activity. The introduction of a substituted phenoxy ring at position 3 enhanced both the in vitro and in vivo activity within the series. A selected group of 3-phenoxypyran-4-ones exhibited excellent activity in an experimental model of pyresis. The in vivo antiinflammatory activity of these compounds was confirmed with the evaluation of their antiarthritic and analgesic effectiveness. Moreover, their pharmacokinetic profile in rats is compatible with a once a day administration by oral route in humans. Within this novel series, compounds 21, 31, 34, and 35 have been selected for further preclinical and clinical evaluation. | Shin SS, Byun Y, Lim KM, Choi JK, Lee KW, Moh JH, Kim JK, Jeong YS, Kim JY, Choi YH, Koh HJ, Park YH, Oh YI, Noh MS, Chung S (2004) In vitro structure-activity relationship and in vivo studies for a novel class of cyclooxygenase-2 inhibitors: 5-aryl-2,2-dialkyl-4-phenyl-3(2H)furanone derivatives. Journal of medicinal chemistry 47, 792-804 (Source: ChEMBL) [PubMed:14761182] [show Abstract] 5-Aryl-2,2-dialkyl-4-phenyl-3(2H)furanone derivatives were studied as a novel class of selective cyclooxygenase-2 inhibitors with regard to synthesis, in vitro SAR, antiinflammatory activities, pharmacokinetic considerations, and gastric safety. 1f, a representative compound for methyl sulfone derivatives, showed a COX-2 IC(50) comparable to that of rofecoxib. In case of 20b, a representative compound for sulfonamide derivatives, a potent antiinflammatory ED(50) of 0.1 mg kg(-1) day(-1) was observed against adjuvant-induced arthritis by a preventive model, positioning 20b as one of the most potent COX-2 inhibitors ever reported. Furthermore, 20b showed strong analgesic activity as indicated by its ED(50) of 0.25 mg/kg against carrageenan-induced thermal hyperalgesia in the Sprague-Dawley rat. 3(2H)Furanone derivatives showed due gastric safety profiles as selective COX-2 inhibitors upon 7-day repeat dosing. A highly potent COX-2 inhibitor of the 3(2H)furanone scaffold could be considered suitable for a future generation COX-2 selective arthritis medication with improved safety profiles. | Chauret N, Yergey JA, Brideau C, Friesen RW, Mancini J, Riendeau D, Silva J, Styhler A, Trimble LA, Nicoll-Griffith DA (2001) In vitro metabolism considerations, including activity testing of metabolites, in the discovery and selection of the COX-2 inhibitor etoricoxib (MK-0663). Bioorganic & medicinal chemistry letters 11, 1059-1062 (Source: ChEMBL) [PubMed:11327589] [show Abstract] Characterization of the metabolites of the COX-2 inhibitor etoricoxib (MK-0663 and L-791,456) produced in vitro indicate formation of an N-oxide pyridine and hydroxymethyl pyridine that can further be glucuronidated or oxidized to an acid. Significant turnover is observed in human hepatocytes. Several CYPs are involved in the oxidative biotranformations and, from in vitro studies, etoricoxib is not a potent CYP3A4 inducer or inhibitor. Based on an in vitro whole blood assay, none of the metabolites of etoricoxib inhibits COX-1 or contributes significantly to the inhibition of COX-2. |
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