Lumiracoxib - CAS 220991-20-8
Catalog number: 220991-20-8
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
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A novel, selective COX-2 inhibitor; Phase 4
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A novel, selective COX-2 inhibitor; Phase 4
Pale Yellow Solid
DMSO 59 mg/mL (200.87 mM); Water <1 mg/mL (<1 mM)
3 years -20°C powder;6 months-80°C in solvent
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1.Two-photon uncageable enzyme inhibitors bearing targeting vectors.
Anstaett P1, Pierroz V, Ferrari S, Gasser G. Photochem Photobiol Sci. 2015 Oct;14(10):1821-5. doi: 10.1039/c5pp00245a.
The activity of two cyclooxygenase-2 enzyme inhibitors, Celecoxib and Lumiracoxib, could be suppressed by coupling to photo-labile protecting groups, so-called photocages. These groups could be further functionalized with a peptide targeting vector for specific cellular delivery. The enzyme inhibition potential of the cyclooxygenase-2 inhibitors could be regained upon two-photon excitation with tissue-transparent near-IR light at 800 nm.
2.Relationship between structural alerts in NSAIDs and idiosyncratic hepatotoxicity: an analysis of spontaneous report data from the WHO database.
Jessurun N1, van Puijenbroek E. Drug Saf. 2015 May;38(5):511-5. doi: 10.1007/s40264-015-0282-z.
BACKGROUND: Idiosyncratic drug reactions such as hepatotoxicity and blood dyscrasias represent one of the major causes of drug withdrawal from the market. According to the reactive metabolite (RM) concept, this may be due to the metabolic activation of structural alerts (SAs), functionalities in the drug molecule that are susceptible to bioactivation resulting in RMs. The relationship, however, between metabolic activation of SAs in drugs with in vivo toxicity measured as disproportionate reporting of adverse drug reactions (ADRs) to the WHO VigiBase™ database has never been studied.
3.Mitochondrial toxicity of selective COX-2 inhibitors via inhibition of oxidative phosphorylation (ATP synthesis) in rat liver mitochondria.
Syed M1, Skonberg C2, Hansen SH3. Toxicol In Vitro. 2016 Apr;32:26-40. doi: 10.1016/j.tiv.2015.12.003. Epub 2015 Dec 9.
Cyclooxygenase-2 (COX-2) inhibitors (coxibs) are non-steroidal anti-inflammatory drugs (NSAIDs) designed to selectively inhibit COX-2. However, drugs of this therapeutic class are associated with drug induced liver injury (DILI) and mitochondrial injury is likely to play a role. The effects of selective COX-2 inhibitors on inhibition of oxidative phosphorylation (ATP synthesis) in rat liver mitochondria were investigated. The order of potency of inhibition of ATP synthesis was: lumiracoxib (IC50: 6.48±2.74μM)>celecoxib (IC50: 14.92±6.40μM)>valdecoxib (IC50: 161.4±28.6μM)>rofecoxib (IC50: 238.4±79.2μM)>etoricoxib (IC50: 405.1±116.3μM). Mechanism based inhibition of ATP synthesis (Kinact 0.078min(-1) and KI 21.46μM and Kinact/KI ratio 0.0036min(-1)μM(-1)) was shown by lumiracoxib and data suggest that the opening of the MPT pore may not be the mechanism of toxicity. A positive correlation (with r(2)=0.921) was observed between the potency of inhibition of ATP synthesis and the log P values.
4.Structure-toxicity relationship and structure-activity relationship study of 2-phenylaminophenylacetic acid derived compounds.
Pang YY1, Yeo WK1, Loh KY2, Go ML1, Ho HK3. Food Chem Toxicol. 2014 Sep;71:207-16. doi: 10.1016/j.fct.2014.06.013. Epub 2014 Jun 20.
2-Phenylaminophenylacetic acid is a widely-exploited chemical scaffold whereby notable NSAIDs such as diclofenac and lumiracoxib were derived. Yet, their clinical usage has been associated with toxicities in the liver. While some studies have attributed toxicities to the bioactivation of both drugs to reactive intermediates, the structural predisposition for toxicity, as well as relationship between this toxicity and COX inhibitory activity has not been elucidated. In this study, we aimed to address their intricate link by synthesizing compounds that possess the 2-phenylaminophenylacetic acid backbone with varying alkyl and halogen substituents at three positions critical to the COX inhibitory pharmacophore. These compounds were subjected to cytotoxicity testing on two liver cell lines of contrasting metabolic competencies. We observed higher toxicity in the more metabolically competent cell line, supporting the role of bioactivation as a prerequisite for toxicity.
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