220991-20-8 Usage
Description
Lumiracoxib, also known by the brand name Prexige, is a second-generation selective cyclooxygenase-2 (COX-2) inhibitor and an anti-inflammatory agent. It is a pale yellow solid that selectively targets COX-2, which is up-regulated in pathological processes of pain and inflammation, without causing gastrointestinal issues associated with non-selective NSAIDs. Lumiracoxib blocks the conversion of arachidonic acid to prostaglandins, the mediators of the pathological effects. It was briefly used for the treatment of osteoarthritis but was withdrawn due to concerns of hepatotoxicity.
Uses
Used in Pharmaceutical Industry:
Lumiracoxib is used as an anti-inflammatory agent for reducing inflammation and pain associated with various conditions. It is particularly effective due to its selective inhibition of COX-2, which minimizes gastrointestinal side effects.
Used in Research and Development:
Lumiracoxib is used as a research tool for studying the role of COX-2 in pain and inflammation, as well as for developing new drugs with similar selective COX-2 inhibition properties.
Used in Drug Metabolism Studies:
Lumiracoxib is used in studies evaluating the impact of drug interactions on its metabolism, such as the co-administration with fluconazole, a potent inhibitor of CYP2C9, which is the primary enzyme responsible for metabolizing lumiracoxib.
Used in Chronic Arthritis Treatment:
Lumiracoxib is used as an anti-inflammatory and analgesic agent for the treatment of chronic arthritis, reducing the severity of arthritic lesions and associated pain.
Used in Air Pouch Inflammation Model:
Lumiracoxib is used in a rat model of air pouch inflammation to study its effects on reducing prostaglandin E2 levels and inflammation.
Used in Infection-Induced Inflammation:
Lumiracoxib is used to reduce inflammation induced by M. tuberculosis, demonstrating its potential application in treating infection-induced inflammatory conditions.
Originator
Novartis AG (Switzerland)
Biochem/physiol Actions
Lumiracoxib (COX189) is an orally active, potent and selective cyclooxygenase-2 inhibitor (Ki = 60 nM/COX-2 vs. 3.2 μM/COX-1) that inhibits COX-2-mediated PGE2 production in human whole blood (IC50 = 130 nM; stimulation = 50 μM A23187), but not COX-1-dependent TxB2 production (IC50 = 67 μM; stimulation = 10 μg/mL LPS). Lumiracoxib shows in vivo anti-inflammatory efficacy against carrageenan-induced paw oedema (ED30 = 0.35 mg/kg p.o.), CFA-induced hyperalgesia (ED30 = 5.1 mg/kg p.o.), as well as adjuvant-induced arthritis (ED50 = 3 mg/kg/day p.o.) in rats in vivo.
Check Digit Verification of cas no
The CAS Registry Mumber 220991-20-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,2,0,9,9 and 1 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 220991-20:
(8*2)+(7*2)+(6*0)+(5*9)+(4*9)+(3*1)+(2*2)+(1*0)=118
118 % 10 = 8
So 220991-20-8 is a valid CAS Registry Number.
InChI:InChI=1/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)
220991-20-8Relevant articles and documents
Designing Multitarget Anti-inflammatory Agents: Chemical Modulation of the Lumiracoxib Structure toward Dual Thromboxane Antagonists-COX-2 Inhibitors
Bertinaria, Massimo,Shaikh, Mohammed Abrar Abdul Gaffar,Buccellati, Carola,Cena, Clara,Rolando, Barbara,Lazzarato, Loretta,Fruttero, Roberta,Gasco, Alberto,Hoxha, Malvina,Capra, Valerie,Sala, Angelo,Rovati, G. Enrico
, p. 1647 - 1660 (2012/11/07)
A series of lumiracoxib derivatives were designed to explore the influence of isosteric substitution on balancing COX-2 inhibition and thromboxane A2 prostanoid (TP) receptor antagonism. The compounds were synthesized through a copper-catalyzed coupling procedure and characterized for their pKa values. TP receptor antagonism was assessed on human platelets; COX-2 inhibition was determined on human isolated monocytes and human whole blood. TPα receptor binding of the most promising compounds was evaluated through radioligand binding assays. Some of the isosteric substitutions at the carboxylic acid group afforded compounds with improved TP receptor antagonism; of these, a tetrazole derivative retained good COX-2 inhibitory activity and selectivity. The identification of this tetrazole acting as a balanced dual-acting compound in human whole blood, along with SAR analysis of the synthesized lumiracoxib derivatives, might contribute to the rational design of a new class of cardioprotective anti-inflammatory agents.
Expedient drug synthesis and diversification via ortho-C-H iodination using recyclable PdI2 as the precatalyst
Mei, Tian-Sheng,Wang, Dong-Hui,Yu, Jin-Quan
supporting information; experimental part, p. 3140 - 3143 (2010/09/03)
(Figure Presented) Pd(II)-catalyzed ortho-C-H iodination reactions of phenylacetic acid substrates have been achieved using recyclable PdI2 as the precatalyst. This class of substrates is incompatible with the classic amide formation/ortho-lithiation/iodination sequence. The power of this new technology is demonstrated by facile drug functionalization and drastically shortened syntheses of the drugs diclofenac and lumiracoxib.
Synthesis of new N-aryl oxindoles as intermediates for pharmacologically active compounds
Acemoglu, Murat,Allmendinger, Thomas,Calienni, John,Cercus, Jacques,Loiseleur, Olivier,Sedelmeier, Gottfried H.,Xu, David
, p. 11571 - 11586 (2007/10/03)
Various new N-aryl oxindoles were synthesized as intermediates for the preparation of pharmacologically active 2-(N-arylamino)-phenylacetic acids. Two novel approaches were explored for the construction of diarylamine and N-aryl oxindole core structures, in addition to Buchwald-arylamination and Smiles rearrangement. Condensation of anilines with 2-oxo-cyclohexylidene-acetic acid derivatives and subsequent dehydrogenation is a new and viable method for the preparation of N-aryl oxindoles. Graphical Abstract.
