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Merck

SML2928

Lumiracoxib

≥98% (HPLC)

Synonym(s):

2-[(2-Chloro-6-fluorophenyl)amino]-5-methyl-benzeneacetic acid, 5-Methyl-2-(2′-chloro-6′-fluoroanilino)phenylacetic acid, CGS 35189, CGS-35189, CGS35189, COX 189, COX-189, COX189, LMX, Non-steroidal anti-inflammatory drug

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About This Item

Empirical Formula (Hill Notation):
C15H13ClFNO2
CAS Number:
220991-20-8
Molecular Weight:
293.72
UNSPSC Code:
51111800
NACRES:
NA.77
MDL number:
MFCD07186254

Product Name

Lumiracoxib, ≥98% (HPLC)

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)

SMILES string

ClC1=CC=CC(F)=C1NC2=CC=C(C)C=C2CC(O)=O

InChI key

KHPKQFYUPIUARC-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

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.
Orally active, potent and selective cyclooxygenase-2 (COX-2) inhibitor with anti-inflammatory efficacy in vivo.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000193565
0000184649
0000165450
0000159833
0000193565

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Amanda Morgan et al.
Neurobiology of stress, 11, 100190-100190 (2019-08-31)
Chronic stress increases the probability of receiving an anxiety, depression, or chronic illness diagnosis. Pharmacological interventions that reduce the behavioral and physiological effects of chronic stress in animal models may represent novel approaches for the treatment of stress-related psychiatric disorders.
Ronald Esser et al.
British journal of pharmacology, 144(4), 538-550 (2005-01-19)
1. This manuscript presents the preclinical profile of lumiracoxib, a novel cyclooxygenase-2 (COX-2) selective inhibitor. 2. Lumiracoxib inhibited purified COX-1 and COX-2 with K(i) values of 3 and 0.06 microM, respectively. In cellular assays, lumiracoxib had an IC(50) of 0.14
Amanda J Morgan et al.
ACS chemical neuroscience, 9(7), 1552-1559 (2018-05-04)
Cyclooxygenase-2 (COX-2) catalyzes the formation of prostaglandins, which are involved in immune regulation, vascular function, and synaptic signaling. COX-2 also inactivates the endogenous cannabinoid (eCB) 2-arachidonoylglycerol (2-AG) via oxygenation of its arachidonic acid backbone to form a variety of prostaglandin
Alyson Fox et al.
Pain, 107(1-2), 33-40 (2004-01-13)
Chronic pain resulting from metastatic bone cancer remains poorly understood and resistant to treatment. Here we have examined the effect of the novel COX-2 enzyme inhibitor lumiracoxib in a model of bone cancer pain in the rat. Lumiracoxib was administered
Weijie Jiao et al.
Drug testing and analysis, 12(6), 827-835 (2020-02-12)
Lumiracoxib is a selective cyclooxygenase-2 inhibitor, which has been reported to cause rare but severe liver injury. Considering that lumiracoxib has a carboxylic group in the molecule, glucuronidation to form acylglucuronide would be one of the possible mechanisms of lumiracoxib-induced
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