5.04924
Indomethacin, 2′-Trifluoromethyl
Synonym(s):
Indomethacin, 2′-Trifluoromethyl, Indomethacin, 2ʹ-Trifluoromethyl; Indomethacin, 2-CF3, CF3-Indomethacin; CF3-INDO
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About This Item
Empirical Formula (Hill Notation):
C19H13ClF3NO4
CAS Number:
Molecular Weight:
411.76
UNSPSC Code:
12352200
PubChem Substance ID:
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
Storage condition:
OK to freeze, protect from light
Quality Level
assay
≥98% (HPLC)
form
powder
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze, protect from light
color
white
solubility
DMSO: 100 mg/mL
storage temp.
2-8°C
SMILES string
COC1=CC2=C(C=C1)N(C(=C2CC(=O)O)C(F)(F)F)C(=O)C3=CC=C(C=C3)Cl
General description
A cell-permeable, bioavailable 2′-trifluoromethyl analog of Indomethacin (>Cat. No. 405268) that acts as a highly potent, time-dependent inhibitor of cyclooxygenase -2 (COX-2; IC50 = 267 and 388 nM for mouse and human COX-2, respectively) and its several mutant forms. Does not affect COX-1 activity even at high concentrations (IC50 >100 µM). Interacts with human COX-2 with much greater affinity than indomethacin (KI = 1.5 vs 13 µM) and blocks COX-2 dependent arachidonic acid oxygenation (IC50 = 150 nM in 1483 human head and neck squamous cell carcinoma cells). Further, minimizes swelling in carrageenan-induced rat paw edema model (EC50 = 1.7 mg/kg, p.o.) with no gastrointestinal bleeding at higher doses (10 mg/kg).
Biochem/physiol Actions
Cell permeable: yes
Primary Target
COX-2
COX-2
Reversible: yes
Target IC50: 267 and 388 nM for mouse and human COX-2, respectively
Packaging
Packaged under inert gas
Preparation Note
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Other Notes
Blobaum, A.L., et al. 2013. ACS Med. Chem. Lett.4, 486.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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