CHEBI:6339 - etoricoxib

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ChEBI Name etoricoxib
ChEBI ID CHEBI:6339
Definition A member of the class of bipyridines that is 2,3'-bipyridine which is substituted at the 3, 5, and 6' positions by 4-(methylsulfonyl)phenyl, chlorine, and methyl groups, respectively.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:106706
Supplier Information ChemicalBook:CB0223494, eMolecules:5758581, ZINC000000579472
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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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Formula C18H15ClN2O2S
Net Charge 0
Average Mass 358.84200
Monoisotopic Mass 358.05428
InChI 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
InChIKey MNJVRJDLRVPLFE-UHFFFAOYSA-N
SMILES Cc1ccc(cn1)-c1ncc(Cl)cc1-c1ccc(cc1)S(C)(=O)=O
Roles Classification
Biological Role(s): cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
Application(s): 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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ChEBI Ontology
Outgoing etoricoxib (CHEBI:6339) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
etoricoxib (CHEBI:6339) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
etoricoxib (CHEBI:6339) is a bipyridines (CHEBI:50511)
etoricoxib (CHEBI:6339) is a organochlorine compound (CHEBI:36683)
etoricoxib (CHEBI:6339) is a sulfone (CHEBI:35850)
IUPAC Name
5-chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-2,3'-bipyridine
INNs Sources
étoricoxib WHO MedNet
etoricoxib WHO MedNet
etoricoxib ChemIDplus
etoricoxibum WHO MedNet
Synonyms Sources
5-chloro-2-(6-methylpyridin-3-yl)-3-(4-(methylsulfonyl)phenyl)pyridine ChEMBL
5-Chloro-3-(4-methanesulfonyl-phenyl)-6'-methyl-[2,3']bipyridinyl ChEMBL
5-chloro-6'-methyl-3-(p-(methylsulfonyl)phenyl)-2,3'-bipyridine ChemIDplus
ETORICOXIB ChEMBL
Etoricoxib KEGG COMPOUND
L791456 KEGG COMPOUND
Manual Xrefs Databases
1113 DrugCentral
5CH PDBeChem
C11718 KEGG COMPOUND
D03710 KEGG DRUG
DB01628 DrugBank
Etoricoxib Wikipedia
LSM-5650 LINCS
View more database links
Registry Numbers Types Sources
202409-33-4 CAS Registry Number KEGG COMPOUND
202409-33-4 CAS Registry Number ChemIDplus
Citations
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]
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]
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]
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]
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]
Last Modified
22 February 2017
General Comment
2011-03-18 A selective inhibitor of cyclooxygenase-2 (COX-2), etoricoxib is used as a non-steroidal anti-inflammatory drug for the symptomatic relief of rheumatoid and osteo-arthritis.