An NSAID and a COX-1 and COX-2 inhibitor
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(S)-Ibuprofen

Item No. 16793

Technical Information
Formal Name
αS-methyl-4-(2-methylpropyl)-benzeneacetic acid
CAS Number
51146-56-6
Synonyms
  • Dexibuprofen
  • (+)-Ibuprofen
Molecular Formula
C13H18O2
Formula Weight
Purity
≥98%
Formulation
A crystalline solid
DMF: 30 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
220 nm
SMILES
OC([C@@H](C)C1=CC=C(CC(C)C)C=C1)=O
InChi Code
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)/t10-/m0/s1
InChi Key
HEFNNWSXXWATRW-JTQLQIEISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    (S)-Ibuprofen is a non-steroidal anti-inflammatory drug (NSAID) and a COX-1 and COX-2 inhibitor (IC50s = 2.6 and 1.53 µM, respectively).1 It inhibits NF-κB transactivation in a reporter assay using Jurkat T cells (IC50 = 61.7 µM).2 (S)-Ibuprofen reduces aggregation in platelet-rich plasma and washed isolated human platelets (IC50s = 88 and 0.6 µM, respectively).3 It decreases superoxide formation and β-glucuronidase release induced by N-formyl-Met-Leu-Phe (fMLP; Item No. 21495), as well as leukotriene B4 (LTB4; Item No. 20110) formation induced by calcimycin (A23187; Item No. 11016), in human polymorphonuclear (PMN) cells (IC50s = 0.50, 0.53, and 0.14 µM, respectively). (S)-Ibuprofen increases the latency to withdrawal in hot plate and tail-flick tests in mice (ED50s = 64 and 54 mg/kg, respectively), as well as reduces paw swelling in a mouse model of carrageenan-induced paw edema (ED50 = 57 mg/kg).4 Formulations containing (±)-ibuprofen have been used in the treatment of fever and mild-to-severe pain.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Barnett, J., Chow, J., Ives, D., et alPurification, characterization and selective inhibition of human prostaglandin G/H synthase 1 and 2 expressed in the baculovirus system. Biochim. Biophys. Acta 1209(1), 130-139 (1994).

    2. Scheuren, N., Bang, H., Münster, T., et alModulation of transcription factor NF-κB by enantiomers of the nonsteroidal drug ibuprofen. Br. J. Pharmacol. 123(4), 645-652 (1998).

    3. Villanueva, M., Heckenberger, R., Strobach, H., et alEquipotent inhibition by R(−)-, S(+)- and racemic ibuprofen of human polymorphonuclear cell function in vitro. Br. J. Clin. Pharmacol. 35(3), 235-242 (1993).

    4. Bonabello, A., Galmozzi, M.R., Canaparo, R., et alDexibuprofen (S+-isomer ibuprofen) reduces gastric damage and improves analgesic and antiinflammatory effects in rodents. Anesth. Analg. 97(2), 402-408 (2003).