An NSAID and isomer of (±)-ibuprofen
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(R)-Ibuprofen

Item No. 16794

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
αR-methyl-4-(2-methylpropyl)-benzeneacetic acid
CAS Number
51146-57-7
Synonyms
  • (-)-Ibuprofen
Molecular Formula
C13H18O2
Formula Weight
206.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 45 mg/mlDMSO: 50 mg/mlEthanol: 60 mg/mlPBS (pH 7.2): 2 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-/m1/s1
InChi Key
HEFNNWSXXWATRW-SNVBAGLBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    (R)-Ibuprofen is a non-steroidal anti-inflammatory drug (NSAID) and an isomer of (±)-ibuprofen (Item No. 70280).1 Unlike (S)-ibuprofen (Item No. 16793), (R)-ibuprofen does not inhibit COX-1 or COX-2 in vitro (IC50s = 360 and 15.6 µM, respectively) but is converted to the active (S)-enantiomer in vivo.2,3 It inhibits NF-κB transactivation in a reporter assay using Jurkat T cells (IC50 = 121.8 µM).1 (R)-Ibuprofen 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 = 0.43, 0.58, and 0.22 µM, respectively).2 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. Scheuren, N., Bang, H., Münster, T., et al. Modulation of transcription factor NF-κB by enantiomers of the nonsteroidal drug ibuprofen. Br. J. Pharmacol. 123(4), 645-652 (1998).

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

    3. Jeffrey, P., Tucker, G.T., Bye, A., et al. The site of inversion of R(–)-ibuprofen: Studies using rat in-situ isolated perfused intestine/liver preparations. J. Pharm. Pharmacol. 43(10), 715-720 (1991).