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10-SEPTEMBER-2008 16:47:15 - Etoricoxib Etoricoxib Systematic IUPAC name 5-chloro-6'-methyl-3-4-methylsulfonylphenyl- 2,3'-bipyridine Identifiers CAS number 202409-33-4 ATC code M01AH05 PubChem 123619 Chemical data Formula C18H15ClN2O2S Mol. mass 358.842 g/mol Pharmacokinetic data Bioavailability 100% Protein binding 92% Metabolism Hepatic, CYP extensively involved mainly CYP3A4 Half life 22 hours Excretion Renal 70% and fecal 20% Therapeutic considerations Pregnancy cat. Not recommended Legal status POMUK Routes Oral Etoricoxib brand name Arcoxia worldwide; also Algix and Tauxib in Italy is a new COX-2 selective inhibitor approx. 106.0 times more selective for COX-2 inhibition over COX-1 from Merck Co. Doses are 60, 90 mg/day for chronic pain and 120 mg/day for acute pain. Currently it is approved in more than 60 countries worldwide but not in the US, where the Food and Drug Administration FDA require additional safety and efficacy data for etoricoxib before it will issue approval. Current therapeutic indications are: treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, chronic low back pain, acute pain and gout. Note that approved indications differ by country. Like any other COX-2 selective inhibitor, Etoricoxib selectively inhibits isoform 2 of cyclo-oxigenase enzyme COX-2. This reduces the generation of prostaglandins PGs from arachidonic acid. Among the different functions exerted by PGs, their role in the inflammation cascade should be highlighted. COX-2 selective inhibitor aka COXIB showed less marked activity on type 1 cycloxigenase compared to traditional non-steroidal anti-inflammatory drugs NSAID. This reduced activity is the cause of reduced gastrointestinal toxicity, as demonstrated in several large clinical trials performed with different COXIB see below links on NEJM and The Lancet. Some clinical trials and meta-analysis showed that treatment with some COXIBs in particular Vioxx, rofecoxib led to increased incidence of adverse cardiovascular events compared to placebo. Because of these results, some molecules were withdrawn from the market Rofecoxib, September 2004 and Valdecoxib, April 2005. In addition, the FDA and EMEA USA and European Community Health Authorities respectively started a revision process of the entire class of both NSAID and COX-2 inhibitors. FDA concluded its revision on April 6, 2005: the final document can be found at: http://www.fda.gov/cder/drug/infopage/COX2/NSAIDdecisionMemo.pdf EMEA concluded its revision on June 27, 2005: the final document can be found at: http://www.emea.europa.eu/pdfs/human/press/pr/20776605en.pdf On April 27, 2007, the Food and Drug Administration issued Merck a non-approvable letter for Arcoxia. The letter said Merck needs to provide more test results showing that Arcoxia's benefits outweigh its risks before it has another chance of getting approved. External links European Medicines Agency EMEA - Homepage - 1 US Food and Drug Administration FDA - Homepage - 2 VIGOR study on The New England Journal of Medicine - NEJM MEDAL study on The Lancet v d e Non-steroidal anti-inflammatory drug NSAID products primarily M01A and M02A, also N02BA Salicylates Aspirin acetylsalicylic acid · Aloxiprin · Benorylate · Diflunisal · Ethenzamide · Magnesium salicylate · Methyl salicylate · Salsalate · Salicin · Salicylamide · Sodium salicylate Arylalkanoic acids Diclofenac · Aceclofenac · Acemetacin · Alclofenac · Bromfenac · Etodolac · Indometacin · Indometacin farnesil · Nabumetone · Oxametacin · Proglumetacin · Sulindac · Tolmetin 2-Arylpropionic acids profens Ibuprofen · Alminoprofen · Benoxaprofen · Carprofen · Dexibuprofen · Dexketoprofen · Fenbufen · Fenoprofen · Flunoxaprofen · Flurbiprofen · Ibuproxam · Indoprofen† · Ketoprofen · Ketorolac · Loxoprofen · Miroprofen · Naproxen · Oxaprozin · Pirprofen · Suprofen · Tarenflurbil · Tiaprofenic acid N-Arylanthranilic acids fenamic acids Mefenamic acid · Flufenamic acid · Meclofenamic acid · Tolfenamic acid Pyrazolidine derivatives Phenylbutazone · Ampyrone · Azapropazone · Clofezone · Kebuzone · Metamizole† · Mofebutazone · Oxyphenbutazone · Phenazone · Sulfinpyrazone Oxicams Piroxicam · Droxicam · Lornoxicam · Meloxicam · Tenoxicam · Ampiroxicam COX-2 inhibitors Celecoxib · Deracoxib‡ · Etoricoxib · Firocoxib‡ · Lumiracoxib† · Parecoxib · Rofecoxib† · Valdecoxib† Sulphonanilides Nimesulide Topically used products Bendazac · Diclofenac · Etofenamate · Felbinac · Flurbiprofen · Ibuprofen · Indometacin · Ketoprofen · Naproxen · Piroxicam · Suprofen Others Fluproquazone · COX-inhibiting nitric oxide donator Items listed in bold indicate initially developed compounds of specific groups. †Withdrawn drugs. ‡Veterinary use medications. v d e Anti-inflammatory and antirheumatic products M01 Anti-inflammatory and antirheumatic products, non-steroids See also: NSAIDs Pyrazolidine/Butylpyrazolidines: · Ampyrone · Clofezone · Kebuzone · Metamizole · Mofebutazone · Oxyphenbutazone · Phenazone · Phenylbutazone · Sulfinpyrazone · Acetic acid derivatives and related substances: · Aceclofenac · Acemetacin · Alclofenac · Bromfenac · Bumadizone · Bufexamac · Diclofenac · Difenpiramide · Etodolac · Fentiazac · Indometacin · Ketorolac · Lonazolac · Oxametacin · Proglumetacin · Sulindac · Tolmetin · Zomepirac · Oxicams: · Ampiroxicam · Droxicam · Lornoxicam · Meloxicam · Piroxicam · Tenoxicam · Propionic acid derivatives: · Alminoprofen · Benoxaprofen · Dexibuprofen · Dexketoprofen · Fenbufen · Fenoprofen · Flunoxaprofen · Flurbiprofen · Ibuprofen · Ibuproxam · Indoprofen · Ketoprofen · Naproxen · Oxaprozin · Pirprofen · Suprofen · Tiaprofenic acid · Fenamates: · Flufenamic acid · Meclofenamic acid · Mefenamic acid · Tolfenamic acid · Coxibs: · Celecoxib · Etoricoxib · Lumiracoxib · Parecoxib · Rofecoxib · Valdecoxib · other anti-inflammatory and antirheumatic agents, non-steroids: · Nabumetone · Niflumic acid · Azapropazone · Glucosamine · Benzydamine · Glycosaminoglycan · Magnesium salicylate · Proquazone · Superoxide dismutase/Orgotein · Nimesulide · Feprazone · Diacerein · Morniflumate · Tenidap · Oxaceprol · Chondroitin sulfate · Specific antirheumatic agents Quinolines: · Oxycinchophen · Gold preparations: · Sodium aurothiomalate · Sodium aurothiosulfate · Auranofin · Aurothioglucose · Aurotioprol · Penicillamine/Bucillamine Tablets This pharmacology-related article is a stub. Retrieved from http://en..org/wiki/Etoricoxib Categories: Non-steroidal anti-inflammatory drugs | Pharmacology stubs Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Türkçe Deutsch Français Italiano Magyar Nederlands This page was last modified on 22 August 2008, at 15:03
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