LUMIRACOXIB

LUMIRACOXIB Basic information
Product Name:LUMIRACOXIB
Synonyms:2-[2-[(2-chloro-6-fluoro-phenyl)amino]-5-methyl-phenyl]acetic acid;2-[(2-Chloro-6-fluorophenyl)amino]-5-methylbenzeneacetic Acid;CGS 35189;COX 189;Prexige;Lumaricoxib;Benzeneacetic acid, 2-((2-chloro-6-fluorophenyl)amino)-5-methyl-;Unii-V91T9204hu
CAS:220991-20-8
MF:C15H13ClFNO2
MW:293.72
EINECS:1308068-626-2
Product Categories:Inhibitors;PREXIGE;Aromatics Compounds;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:220991-20-8.mol
LUMIRACOXIB Structure
LUMIRACOXIB Chemical Properties
Melting point 139-141°C
Boiling point 395.7±42.0 °C(Predicted)
density 1.363±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility ≥29.4 mg/mL in DMSO; insoluble in H2O; ≥27.15 mg/mL in EtOH with ultrasonic
pka4.18±0.10(Predicted)
form solid
CAS DataBase Reference220991-20-8
Safety Information
MSDS Information
LUMIRACOXIB Usage And Synthesis
DescriptionAs a second-generation, selective cyclooxygenase (COX-2) inhibitor, lumiracoxib is devoid of the gastrointestinal issues that plague other non-selective, nonsteroidal, anti-inflammatory drugs (NSAIDs) that crossover to COX-1. As an inhibitor of the inducible COX-2 that is up-regulated in pathological processes of pain and inflammation, lumiracoxib blocks the conversion of arachidonic acid to prostaglandins, the mediators of the pathological effects. It’s mode of binding to COX-2 has been found to differ from the other selective COX-2 inhibitors; the carboxylic acid forms hydrogen bonds with Tyr-385 and Ser-530 in the catalytic site rather than seeking interactions within the larger hydrophobic side pocket. Since lumiracoxib is mainly metabolized by CYP2C9, a study evaluating the co-administration of lumiracoxib with fluconazole, a potent inhibitor of CYP2C9, was conducted, and it concluded that there was no need for lumiracoxib dose adjustment, since changes in the systemic exposure were not significant. No serious adverse effects were reported, but in the small number of cases where treatment was discontinued, Gastro intestinal (GI) and musculoskeletal complaints were common.
DescriptionLumiracoxib is a selective inhibitor of COX-2 with IC50 values of 0.13 and 67 μM for COX-2 and COX-1, respectively, in isolated human whole blood. It reduces increases in the levels of prostaglandin E2 (PGE2; ) induced by IL-1β in human dermal fibroblasts (IC50 = 0.14 μM), as well as in LPS-stimulated RAW 264.7 cells when used at concentrations ranging from 1 to 100 μM., Lumiracoxib (3 and 10 mg/kg) also decreases LPS-induced increases in the levels of PGE2 in a rat model of air pouch inflammation. It reduces M. tuberculosis-induced increases in hind paw volume and the radiological and histopathological severity of arthritic lesions in a rat model of chronic arthritis when administered at a dose of 2 mg/kg.
Chemical PropertiesPale Yellow Solid
OriginatorNovartis AG (Switzerland)
UsesLumiracoxib is a selective cyclooxygenase-2-(COX-2) inhibitor and an anti-inflammatory agent (1,2,3,4).
UsesSelective cyclooxygenase-2-(COX-2) inhibitor. Anti-inflammatory.
Usesantiinflammatory, analgesic, antiarthritic
DefinitionChEBI: An amino acid that is phenylacetic acid which is substituted at position 2 by the nitrogen of 2-chloro-6-fluoroaniline and at position 5 by a methyl group. A highly selective cyclooxygenase 2 inhibitor, it was briefly used for the treatment of osteoarthrit s, but was withdrawn due to concersns of hepatotoxicity.
Brand namePrexige
Biochem/physiol ActionsLumiracoxib (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.
LUMIRACOXIB Preparation Products And Raw materials
Apremilast Cimetidine Rofecoxib Esomeprazole Indole (2-CHLORO-6-FLUOROPHENYL)-P-TOLYL-AMINE LUMIRACOXIB 2,4-Dimethyldiphenylamine 2-Chloro-6-fluoroaniline 2-ANILINOPHENYLACETIC ACID 2-FLUORODIPHENYLAMINE

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