The COX-active enantiomer of flurbiprofen
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Active Metabolite(s)
216914'-hydroxy Flurbiprofen
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(S)-Flurbiprofen

Item No. 10004207

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(S)-(+)-2-fluoro-α-methyl-4-biphenylacetic acid
CAS Number
51543-39-6
Molecular Formula
C15H13FO2
Formula Weight
244.3
Purity
≥99%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 10 mg/mlEthanol: 25 mg/mlPBS (pH 7.2): 0.9 mg/ml
λmax
247 nm
SMILES
FC1=CC([C@@H](C(O)=O)C)=CC=C1C2=CC=CC=C2
InChi Code
InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18)
InChi Key
SYTBZMRGLBWNTM-UHFFFAOYSA-N
Shipping & Storage Information
Storage
Room temperature
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

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    Product Description

    (S)-Flurbiprofen is the COX-active enantiomer of the non-selective COX inhibitor flurbiprofen (Item No. 70250) with IC50 values of 0.48 and 0.47 µM for COX-1 and COX-2, respectively, in guinea pig whole blood.1 It inhibits the release of 6-keto prostaglandin F1α (6-keto-PGF1α; Item No. 15210) and thromboxane B2 (TXB2; Item No. 19030) from rat whole blood, gastric mucosa, lung, and jejunal tissue ex vivo in a dose-dependent manner.2 (S)-Flurbiprofen (1 nM) inhibits basal and bradykinin-, serotonin-, and histamine-stimulated prostaglandin E2 (PGE2) release from isolated skin flaps of rat lower hind paws.3 It also inhibits release of the neuroinflammatory marker calcitonin gene-related peptide (CGRP; Item Nos. 24405 | 24725 | 24728) when used at a concentration of 1 μM. In vivo, (S)-flurbiprofen reduces the number of flinches per minute in the formalin test in rats, indicating antinociceptive activity.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Carabaza, A., Cabre, F., Rotllan, E., et al. Stereoselective inhibition of inducible cyclooxygenase by chiral nonsteroidal antiinflammatory drugs. J. Clin. Pharmacol. 36, 505-512 (1996).

    2. Peskar, B.M., Kluge, S., Peskar, B.A., et al. Effects of pure enantiomers of flurbiprofen in comparison to racemic flurbiprofen on eicosanoid release from various rat organs ex vivo. Prostaglandins 42(6), 515-531 (1991).

    3. Averbeck, B., Peisler, M., Izydorczyk, I., et al. Inflammatory mediators do not stimulate CGRP release if prostaglandin synthesis is blocked by S(+)-flurbiprofen in isolated rat skin. Inflamm. Res. 52(12), 519-523 (2003).

    4. Malmberg, A.B., and Yaksh, T.L. Antinociception produced by spinal delivery of the S and R enantiomers of flurbiprofen in the formalin test. Eur. J. Pharmacol. 256(2), 205-209 (1994).