401003

(±)-Ibuprofen

A nonsteroidal anti-inflammatory drug (NSAID) that acts as a reversible and competitive inhibitor of cyclooxygenase 1 (COX-1) (IC₅₀ = 4.85 µM).

• Synonym(s): (±)-Ibuprofen, [(±)-2-(4-Isobutylphenyl)-propionic Acid
• Empirical Formula (Hill Notation): C₁₃H₁₈O₂
• CAS Number: 15687-27-1
• Molecular Weight: 206.28
• NACRES: NA.77
• MDL number: MFCD00010393
• UNSPSC Code: 12352200
• Assay: ≥98% (titration)
• Form: solid
• Storage condition: OK to freeze, protect from light

Properties

• Quality Segment: 100
• description: Merck USA index - 14, 4881
• assay: ≥98% (titration)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: white
• solubility: ethanol: 1 mg/mL, DMSO: 5 mg/mL
• shipped in: ambient
• storage temp.: 10-30°C
• SMILES string: OC(=O)C(C)c1ccc(cc1)CC(C)C
• InChI: 1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)
• InChI key: HEFNNWSXXWATRW-UHFFFAOYSA-N

Description

General description

A nonsteroidal anti-inflammatory drug (NSAID) that acts as a reversible, competitive, non-selective cyclooxygenase (COX) inhibitor (IC₅₀ = 4.85 µM for purified COX-1 and 223 µM for purified COX-2). Also reported to inhibit COX-1 and COX-2 activity in intact bovine aortic endothelial cells (BAEC) (IC₅₀ = 7 µM for COX-1 and 72.7 µM for COX-2). Potently blocks aspirin inactivation of COX-1 (EC₅₀ antagonism of 200 µM aspirin ~290 nM for ovine COX-1). Decreases the secretion of total Aβ (Amyloid β_40&42) by human neuronal cells and offers neuroprotection against glutamate-, nitric oxide- and superoxide-induced damage. Activates peroxisome proliferator activated receptors α and γ in both CV-1 and C3H10T1/2 cells (~100 µM - 500 µM).

Biochem/physiol Actions

Cell permeable: no

Primary Target
COX-1

Product competes with ATP.

Reversible: yes

Target IC₅₀: 4.85 µM against COX-1

Preparation Note

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Asanuma, M., et al. 2001. J. Neurochem.76, 1895.
Blasko, I., et al. 2001. Neurobiol. Dis.8, 1094.
Ouellet, M., et al. 2001. Proc. Natl. Acad. Sci. USA98, 14583.
Casper, D., et al. 2000. Neurosci. Lett.289, 201.
Lambat, Z., et al. 2000. Metab. Brain Dis.15, 249.
Lim, G.P., et al. 2000. J. Neurosci.20, 5709.
Ogawa, O., et al. 2000. Eur. J. Pharmacol.408, 137.
Wyss-Coray, T., and Mucke, L. 2000. Nat. Med.6, 973.
Lehmann, J.M., et al. 1997. J. Biol. Chem.272, 3406.
Boneburg, E.M., et al. 1996. J. Clin. Pharmacol.36, 16S.
Mitchell, J.A., et al. 1994. Proc. Natl. Acad. Sci. USA90, 11693.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Harmful (C)

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P301 + P312 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable