Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H15ClN2O2S.ClH |
Molecular Weight | 395.303 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC1=NC=C(C=C1)C2=C(C=C(Cl)C=N2)C3=CC=C(C=C3)S(C)(=O)=O
InChI
InChIKey=NNGHGPAKTWAHHB-UHFFFAOYSA-N
InChI=1S/C18H15ClN2O2S.ClH/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;1H
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11160644
Curator's Comment: # Merck Research Laboratories
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) |
5.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | ARCOXIA Approved UseARCOXIA is indicated in the symptomatic relief of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis and the pain and signs of inflammation associated with acute gouty arthritis. Launch Date2004 |
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Palliative | ARCOXIA Approved UseARCOXIA is indicated in the symptomatic relief of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis and the pain and signs of inflammation associated with acute gouty arthritis. Launch Date2004 |
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Palliative | ARCOXIA Approved UseARCOXIA is indicated in the symptomatic relief of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis and the pain and signs of inflammation associated with acute gouty arthritis. Launch Date2004 |
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Primary | ARCOXIA Approved UseARCOXIA is indicated in the symptomatic relief of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis and the pain and signs of inflammation associated with acute gouty arthritis. Launch Date2004 |
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Palliative | ARCOXIA Approved UseARCOXIA is indicated in the symptomatic relief of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis and the pain and signs of inflammation associated with acute gouty arthritis. Launch Date2008 |
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Primary | ARCOXIA Approved UseARCOXIA is indicated in the symptomatic relief of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis and the pain and signs of inflammation associated with acute gouty arthritis. Launch Date2004 |
PubMed
Title | Date | PubMed |
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A comparison of the therapeutic efficacy and tolerability of etoricoxib and diclofenac in patients with osteoarthritis. | 2003 |
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Treatment of chronic low back pain with etoricoxib, a new cyclo-oxygenase-2 selective inhibitor: improvement in pain and disability--a randomized, placebo-controlled, 3-month trial. | 2003 Aug |
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The role of cyclooxygenase selective inhibitors in the gastrointestinal tract. | 2003 Dec |
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[Rapidly acting and powerful antirheumatic drug now also approved in Germany. Arcoxia (etoricoxib, MSD)]]. | 2004 |
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Etoricoxib reduced pain and disability and improved quality of life in patients with chronic low back pain: a 3 month, randomized, controlled trial. | 2004 |
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Economic evaluation of etoricoxib versus non-selective NSAIDs in the treatment of osteoarthritis and rheumatoid arthritis patients in the UK. | 2004 |
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A mechanistic perspective on the specificity and extent of COX-2 inhibition in pregnancy. | 2004 |
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Selective cyclooxygenase-2 inhibitors: similarities and differences. | 2004 |
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Clinical pharmacology of novel selective COX-2 inhibitors. | 2004 |
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[Pharmacology and classification of cyclooxygenase inhibitors]. | 2004 Apr |
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The second generation of COX-2 inhibitors: clinical pharmacological point of view. | 2004 Aug |
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First and second generations of COX-2 selective inhibitors. | 2004 Aug |
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Use of gastroprotective agents and discontinuations due to dyspepsia with the selective cyclooxygenase-2 inhibitor etoricoxib compared with non-selective NSAIDs. | 2004 Dec |
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[Comparison of preemptive analgesia efficacy between etoricoxib and rofecoxib in ambulatory gynecological surgery]. | 2004 Dec |
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Isolation and structural characterization of the photolysis products of etoricoxib. | 2004 Dec |
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Novel insights and therapeutical applications in the field of inhibitors of COX-2. | 2004 Dec |
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Sulfone COX-2 inhibitors increase susceptibility of human LDL and plasma to oxidative modification: comparison to sulfonamide COX-2 inhibitors and NSAIDs. | 2004 Dec |
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Cyclooxygenase-2 inhibitors: do they have a role in emergency department prescribing? | 2004 Feb |
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Efficacy and safety profile of treatment with etoricoxib 120 mg once daily compared with indomethacin 50 mg three times daily in acute gout: a randomized controlled trial. | 2004 Feb |
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Renal effects of etoricoxib and comparator nonsteroidal anti-inflammatory drugs in controlled clinical trials. | 2004 Jan |
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Pharmacokinetics of etoricoxib in patients with renal impairment. | 2004 Jan |
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Gateways to clinical trials. | 2004 Jan-Feb |
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Gastrointestinal side-effects of traditional non-steroidal anti-inflammatory drugs and new formulations. | 2004 Jul |
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Gateways to clinical trials. | 2004 Jul-Aug |
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Etoricoxib. | 2004 May |
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[Etoricoxib (Arcoxia)]. | 2004 May |
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Etoricoxib in acute pain associated with dental surgery: a randomized, double-blind, placebo- and active comparator-controlled dose-ranging study. | 2004 May |
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Evaluation of quality of life following treatment with etoricoxib in patients with arthritis or low-back pain: an open label, uncontrolled pilot study in Mexico. | 2004 May |
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Cyclooxygenases: new forms, new inhibitors, and lessons from the clinic. | 2004 May |
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A randomized, double-blind, parallel-group study comparing the analgesic effect of etoricoxib to placebo, naproxen sodium, and acetaminophen with codeine using the dental impaction pain model. | 2004 May-Jun |
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Gateways to clinical trials. | 2004 Nov |
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Gateways to clinical trials. | 2004 Oct |
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The effects of modifying in vivo cytochrome P450 3A (CYP3A) activity on etoricoxib pharmacokinetics and of etoricoxib administration on CYP3A activity. | 2004 Oct |
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Gateways to clinical trials. | 2004 Sep |
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The analgesic efficacy of etoricoxib compared with oxycodone/acetaminophen in an acute postoperative pain model: a randomized, double-blind clinical trial. | 2004 Sep |
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Cyclo-oxygenase-2 inhibitors: when should they be used in the elderly? | 2005 |
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Evaluation of the comparative efficacy of etoricoxib and ibuprofen for treatment of patients with osteoarthritis: A randomized, double-blind, placebo-controlled trial. | 2005 Apr |
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Evaluation of the efficacy of etoricoxib in ankylosing spondylitis: results of a fifty-two-week, randomized, controlled study. | 2005 Apr |
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Quantitation of itopride in human serum by high-performance liquid chromatography with fluorescence detection and its application to a bioequivalence study. | 2005 Apr 25 |
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The molecular basis for coxib inhibition of p38alpha MAP kinase. | 2005 Aug 1 |
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Validated liquid chromatographic ultraviolet method for the quantitation of Etoricoxib in human plasma using liquid-liquid extraction. | 2005 Feb 25 |
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Regulation of thrombomodulin expression in human vascular smooth muscle cells by COX-2-derived prostaglandins. | 2005 Jan 7 |
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Gateways to clinical trials. | 2005 Jan-Feb |
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Valdecoxib: assessment of cyclooxygenase-2 potency and selectivity. | 2005 Mar |
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A liquid chromatography-mass spectrometry method for the quantification of both etoricoxib and valdecoxib in human plasma. | 2005 Mar |
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The incidence of upper gastrointestinal adverse events in clinical trials of etoricoxib vs. non-selective NSAIDs: an updated combined analysis. | 2005 May |
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Etoricoxib: a highly selective COX-2 inhibitor. | 2005 May |
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Efficacy of cyclo-oxygenase-2 inhibition by etoricoxib and naproxen on the axial manifestations of ankylosing spondylitis in the presence of peripheral arthritis. | 2005 Nov |
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An overview of the recent developments in analytical methodologies for determination of COX-2 inhibitors in bulk drugs, pharmaceuticals and biological matrices. | 2005 Sep 15 |
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Simultaneous quantitation of etoricoxib, salicylic acid, valdecoxib, ketoprofen, nimesulide and celecoxib in plasma by high-performance liquid chromatography with UV detection. | 2006 Jan |
Patents
Sample Use Guides
The recommended dose is 30 mg once a day (osteoarthritis) and 60 mg once a day (rheumatoid arthritis, ankylosing spondylitis); the dose may be increased to a maximum of 60 mg (osteoarthritis) or 90 mg (rheumatoid arthritis, ankylosing spondylitis) once a day if needed. In case of acute pain conditions etoricoxib should be used only for the acute painful period. In gout the recommended dose is 120 mg once a day which should only be used for the acute painful period, limited to a maximum of 8 days. For the treatment of postoperative dental surgery pain the recommended dose is 90 mg once daily, limited to a maximum of 3 days treatment.
Route of Administration:
Oral
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17895326
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138Y28RY5E
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202409-40-3
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DBSALT002328
Created by
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ACTIVE MOIETY
SUBSTANCE RECORD