Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H13ClFNO2 |
Molecular Weight | 293.721 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC=C(NC2=C(Cl)C=CC=C2F)C(CC(O)=O)=C1
InChI
InChIKey=KHPKQFYUPIUARC-UHFFFAOYSA-N
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)
DescriptionSources: https://www.drugbank.ca/drugs/DB01283Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/15311562
Sources: https://www.drugbank.ca/drugs/DB01283
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/15311562
Lumiracoxib is a COX-2 selective inhibitor non-steroidal anti-inflammatory drug. On August 11, 2007, Australia's 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. It has never been approved for use in the United States. Lumiracoxib has a different structure from the standard COX-2 inhibitors (e.g. celecoxib). It more closely resembles the structure of diclofenac (one chlorine substituted by fluorine, the phenylacetic acid has another methyl group in meta position), making it a member of the arylalkanoic acid family of NSAIDs. It binds to a different site on the COX-2 receptor than the standard COX-2 inhibitors. It displays extremely high COX-2 selectivity. The mechanism of action of lumiracoxib is due to inhibition of prostaglandin synthesis via inhibition of cyclooygenase-2 (COX-2). Lumiracoxib does not inhibit COX-1 at therapeutic concentrations. Lumiracoxib is used for the acute and chronic treatment of the signs and symptoms of osteoarthritis of the knee in adults.
Originator
Sources: http://adisinsight.springer.com/drugs/800014634
Curator's Comment: # Novartis
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL230 Sources: https://www.drugbank.ca/drugs/DB01283 |
3.5 nM [IC50] | ||
Target ID: CHEMBL221 Sources: https://www.drugbank.ca/drugs/DB01283 |
3.22 µM [IC50] | ||
Target ID: CHEMBL1641348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20877132 |
1.9 µM [IC50] | ||
Target ID: CHEMBL1641347 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20877132 |
3.3 µM [IC50] | ||
Target ID: CHEMBL396 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18466679 |
833.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | Prexige Approved UseLumiracoxib (tradename Prexige) was approved for the indications:
Symptomatic relief in the treatment of osteoarthritis.
Relief of acute pain, including post-operative pain and pain related to dental procedures.
Relief of pain due to primary dysmenorrhoea. Launch Date1.08855362E12 |
|||
Palliative | Prexige Approved UseLumiracoxib (tradename Prexige) was approved for the indications:
Symptomatic relief in the treatment of osteoarthritis.
Relief of acute pain, including post-operative pain and pain related to dental procedures.
Relief of pain due to primary dysmenorrhoea. Launch Date1.08855362E12 |
PubMed
Title | Date | PubMed |
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COX-2 drug may help treat osteoarthritis. | 2004 Dec |
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The future of traditional nonsteroidal antiinflammatory drugs and cyclooxygenase-2 inhibitors in the treatment of inflammation and pain. | 2005 |
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Clinical pharmacology of lumiracoxib: a selective cyclo-oxygenase-2 inhibitor. | 2005 |
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Cardiovascular and gastrointestinal effects of COX-2 inhibitors and NSAIDs: achieving a balance. | 2005 |
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Current state of therapy for pain and inflammation. | 2005 |
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Efficacy and tolerability of lumiracoxib 100 mg once daily in knee osteoarthritis: a 13-week, randomized, double-blind study vs. placebo and celecoxib. | 2005 Apr |
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Clinical pharmacology of lumiracoxib, a second-generation cyclooxygenase 2 selective inhibitor. | 2005 Apr |
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Peripheral and spinal mechanisms of antinociceptive action of lumiracoxib. | 2005 Apr 18 |
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Cardiovascular safety of lumiracoxib: a meta-analysis of all randomized controlled trials > or =1 week and up to 1 year in duration of patients with osteoarthritis and rheumatoid arthritis. | 2005 Aug |
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Monocyte cyclooxygenase-2 activity: a new therapeutic target for atherosclerosis? | 2005 Aug |
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Update on cyclooxygenase inhibitors: has a third COX isoform entered the fray? | 2005 Aug |
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Treatment of osteoarthritis of the knee with a topical diclofenac solution: a randomised controlled, 6-week trial [ISRCTN53366886]. | 2005 Aug 8 |
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Gateways to clinical trials. | 2005 Dec |
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Oral administration of lumiracoxib reduces choroidal neovascular membrane development in the rat laser-trauma model. | 2005 Dec |
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The safety of lumiracoxib when used in the treatment of arthritis. | 2005 Feb |
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Preclinical pharmacology of lumiracoxib: a novel selective inhibitor of cyclooxygenase-2. | 2005 Feb |
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Safety and efficacy of lumiracoxib compared with NSAIDs. | 2005 Jan |
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Lumiracoxib in the treatment of osteoarthritis, rheumatoid arthritis and acute postoperative dental pain: results of three dose-response studies. | 2005 Jan |
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Efficacy and tolerability of lumiracoxib in the treatment of osteoarthritis of the knee: a 13-week, randomized, double-blind comparison with celecoxib and placebo. | 2005 Jan |
|
Gateways to clinical trials. | 2005 Jan-Feb |
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Efficacy of lumiracoxib in osteoarthritis: a review of nine studies. | 2005 Jan-Feb |
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Gateways to clinical trials. | 2005 Jul-Aug |
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Relative thromboembolic risks associated with COX-2 inhibitors. | 2005 Jul-Aug |
|
[Lumiracoxib reduces ulcer complications in comparison to NSAR]. | 2005 Mar-Apr |
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Lumiracoxib reduced ulcer complications compared with ibuprofen and naproxen in osteoarthritis and did not increase cardiovascular outcomes. | 2005 Mar-Apr |
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Pharmacodynamic behaviour of the selective cyclooxygenase-2 inhibitor lumiracoxib in the lipopolysaccharide-stimulated rat air pouch model. | 2005 May |
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Gateways to clinical trials. | 2005 Nov |
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The post-operative analgesic efficacy and tolerability of lumiracoxib compared with placebo and naproxen after total knee or hip arthroplasty. | 2005 Nov |
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Lumiracoxib is effective in the treatment of episodic tension-type headache. | 2005 Oct |
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Lumiracoxib does not affect the ex vivo antiplatelet aggregation activity of low-dose aspirin in healthy subjects. | 2005 Oct |
|
Risk of acute myocardial infarction with nonselective non-steroidal anti-inflammatory drugs: a meta-analysis. | 2006 |
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Patients, their doctors, nonsteroidal anti-inflammatory drugs and the perception of risk. | 2006 |
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First-dose analgesic effect of the cyclo-oxygenase-2 selective inhibitor lumiracoxib in osteoarthritis of the knee: a randomized, double-blind, placebo-controlled comparison with celecoxib [NCT00267215]. | 2006 |
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Differential direct effects of cyclo-oxygenase-1/2 inhibition on proteoglycan turnover of human osteoarthritic cartilage: an in vitro study. | 2006 |
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Different COX-independent effects of the COX-2 inhibitors etoricoxib and lumiracoxib. | 2006 Apr 14 |
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Systemic inflammation induces COX-2 mediated prostaglandin D2 biosynthesis in mice spinal cord. | 2006 Feb |
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Lumiracoxib is effective in the treatment of osteoarthritis of the knee: a prospective randomized 13-week study versus placebo and celecoxib. | 2006 Feb |
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Gastrointestinal tolerability of lumiracoxib in patients with osteoarthritis and rheumatoid arthritis. | 2006 Jan |
|
Systematic review: coxibs, non-steroidal anti-inflammatory drugs or no cyclooxygenase inhibitors in gastroenterological high-risk patients? | 2006 Jan 1 |
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Gateways to clinical trials. | 2006 Jan-Feb |
|
Gateways to clinical trials. | 2006 Jul-Aug |
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Influence of plasma protein on the potencies of inhibitors of cyclooxygenase-1 and -2. | 2006 Mar |
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[Cyclooxygenase-2: a new therapeutic target in atherosclerosis?]. | 2006 May 27 |
|
Accounting for the increase in NSAID expenditure: substitution or leakage? | 2006 May 31 |
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Selective COX-2 inhibitors and risk of thromboembolic events - regulatory aspects. | 2006 Oct |
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COX-2 inhibitors and cardiovascular risk. Inferences based on biology and clinical studies. | 2006 Oct |
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A validated high-performance liquid chromatographic assay for determination of lumiracoxib in human plasma. | 2006 Oct |
|
Adverse effects of cyclooxygenase 2 inhibitors on renal and arrhythmia events: meta-analysis of randomized trials. | 2006 Oct 4 |
|
Gateways to clinical trials. | 2006 Sep |
|
Cardioprotective aspirin users and their excess risk of upper gastrointestinal complications. | 2006 Sep 20 |
Patents
Sample Use Guides
Oral
Osteoarthritis of the knee
Adult: 100 mg once daily. Max: 400 mg/day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18466679
Lumiracoxib (15 - 240 umol/L) has an inhibitory effect on the proliferation of A549 and NCI-H460 cell lines in concentration- and time-dependent manners with the IC50 values of 2597 umol/L and 833 umol/L, respectively.
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C1323
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QM01AH06
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M01AH06
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CHEMBL404108
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1618
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C473384
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LUMIRACOXIB
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151166
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100000084778
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m6931
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OO-27
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DB01283
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73044
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SUB21406
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220991-20-8
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2897
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C66041
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