Synonym
CGS-35189; CGS 35189; CGS35189; COX-189; COX189; COX 189; Lumiracoxib; trade name: Prexige.
IUPAC/Chemical Name
2-(2-((2-chloro-6-fluorophenyl)amino)-5-methylphenyl)acetic acid
InChi Key
KHPKQFYUPIUARC-UHFFFAOYSA-N
InChi Code
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 Code
O=C(O)CC1=CC(C)=CC=C1NC2=C(F)C=CC=C2Cl
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Lumiracoxib (COX-189) is a COX1 and COX2 inhibitor with Ki of 3 μM and 0.06 μM, respectively.
In vitro activity:
Lumiracoxib (15 - 240 micromol/L) had 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 micromol/L and 833 micromol/L, respectively. Fluorescent staining showed that lumiracoxib could induce apoptosis in A549 and NCI-H460 cells. Lumiracoxib treatment also caused an increase of the sub-G1 fraction in each cell line and resulted in an increase of G0/G1-phase cells and a decrease of S-phase cells.
Reference: Chin Med J (Engl). 2008 Apr 5;121(7):602-7. https://insights.ovid.com/pubmed?pmid=18466679
In vivo activity:
Selective cyclooxygenase-2 inhibitor lumiracoxib was shown to have the strong inhibitory potencies on the renal organic anion transporter (OAT)1 and also on OAT3 from drug transport experiments. The effect of lumiracoxib on disposition of phenolsulfonphthalein (PSP) - which is mainly excreted into urine via OATs – was studied in vivo After the intravenous injection of PSP and lumiracoxib into rats, pharmacokinetic analysis was performed. After the intravenous injection of PSP as a bolus, its plasma concentration decreased time-dependently. Until 60 min after the injection, 51.1% of the dose was recovered into urine. The simultaneous administration of lumiracoxib increased the plasma levels of PSP and reduced its urinary recovery to 23.6% of the dose. The pharmacokinetic analysis using a two-compartment model exhibited that lumiracoxib affected the parameters implying the elimination of PSP. The present study demonstrates that lumiracoxib interfered with urinary excretion of PSP in rats.
Reference: Drug Metabol Drug Interact. 2014;29(3):203-6. https://pubmed.ncbi.nlm.nih.gov/24870608/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
30.0 |
102.14 |
| DMSO |
44.5 |
151.50 |
| DMSO:PBS (pH 7.2) (1:4) |
0.2 |
0.68 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
293.72
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Hao JQ, Li Q, Xu SP, Shen YX, Sun GY. Effect of lumiracoxib on proliferation and apoptosis of human nonsmall cell lung cancer cells in vitro. Chin Med J (Engl). 2008 Apr 5;121(7):602-7. PMID: 18466679.
2. Honjo H, Uwai Y, Nabekura T. Effect of selective cyclooxygenase-2 inhibitor lumiracoxib on phenolsulfonphthalein disposition in rats. Drug Metabol Drug Interact. 2014;29(3):203-6. doi: 10.1515/dmdi-2014-0008. PMID: 24870608.
In vitro protocol:
1. Hao JQ, Li Q, Xu SP, Shen YX, Sun GY. Effect of lumiracoxib on proliferation and apoptosis of human nonsmall cell lung cancer cells in vitro. Chin Med J (Engl). 2008 Apr 5;121(7):602-7. PMID: 18466679.
In vivo protocol:
1. Honjo H, Uwai Y, Nabekura T. Effect of selective cyclooxygenase-2 inhibitor lumiracoxib on phenolsulfonphthalein disposition in rats. Drug Metabol Drug Interact. 2014;29(3):203-6. doi: 10.1515/dmdi-2014-0008. PMID: 24870608.
1: Silva RC, Riera R, Saconato H. Lumiracoxib for acute postoperative dental pain: a systematic review of randomized clinical trials. Sao Paulo Med J. 2011;129(5):335-45. Review. PubMed PMID: 22069133.
2: Roy YM, Derry S, Moore RA. Single dose oral lumiracoxib for postoperative pain in adults. Cochrane Database Syst Rev. 2010 Jul 7;(7):CD006865. doi: 10.1002/14651858.CD006865.pub2. Review. PubMed PMID: 20614451; PubMed Central PMCID: PMC4164453.
3: Chen YF, Jobanputra P, Barton P, Bryan S, Fry-Smith A, Harris G, Taylor RS. Cyclooxygenase-2 selective non-steroidal anti-inflammatory drugs (etodolac, meloxicam, celecoxib, rofecoxib, etoricoxib, valdecoxib and lumiracoxib) for osteoarthritis and rheumatoid arthritis: a systematic review and economic evaluation. Health Technol Assess. 2008 Apr;12(11):1-278, iii. Review. PubMed PMID: 18405470.
4: Roy YM, Derry S, Moore RA. Single dose oral lumiracoxib for postoperative pain. Cochrane Database Syst Rev. 2007 Oct 17;(4):CD006865. Review. Update in: Cochrane Database Syst Rev. 2010;(7):CD006865. PubMed PMID: 17943921; PubMed Central PMCID: PMC4158423.
5: Yuan Y, Hunt RH. Global gastrointestinal safety profile of etoricoxib and lumiracoxib. Curr Pharm Des. 2007;13(22):2237-47. Review. PubMed PMID: 17691997.
6: Bannwarth B, Bérenbaum F. Lumiracoxib in the management of osteoarthritis and acute pain. Expert Opin Pharmacother. 2007 Jul;8(10):1551-64. Review. PubMed PMID: 17661736.
7: Buvanendran A, Barkin R. Lumiracoxib. Drugs Today (Barc). 2007 Mar;43(3):137-47. Review. PubMed PMID: 17380211.
8: Rordorf CM, Choi L, Marshall P, Mangold JB. Clinical pharmacology of lumiracoxib: a selective cyclo-oxygenase-2 inhibitor. Clin Pharmacokinet. 2005;44(12):1247-66. Review. PubMed PMID: 16372823.
9: Matchaba P, Gitton X, Krammer G, Ehrsam E, Sloan VS, Olson M, Mellein B, Hoexter G, Orloff J, Garaud JJ. 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. Clin Ther. 2005 Aug;27(8):1196-214. Review. PubMed PMID: 16199245.
10: Bannwarth B, Berenbaum F. Clinical pharmacology of lumiracoxib, a second-generation cyclooxygenase 2 selective inhibitor. Expert Opin Investig Drugs. 2005 Apr;14(4):521-33. Review. PubMed PMID: 15882125.
11: Doggrell SA. The safety of lumiracoxib when used in the treatment of arthritis. Expert Opin Pharmacother. 2005 Feb;6(2):347-50. Review. PubMed PMID: 15757430.
12: Mysler E. Lumiracoxib (Prexige): a new selective COX-2 inhibitor. Int J Clin Pract. 2004 Jun;58(6):606-11. Review. PubMed PMID: 15311562.
