A major active metabolite of flurbiprofen
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4'-hydroxy Flurbiprofen

Item No. 21691

Technical Information
Formal Name
2-fluoro-4'-hydroxy-α-methyl-[1,1'-biphenyl]-4-acetic acid
CAS Number
52807-12-2
Molecular Formula
C15H13FO3
Formula Weight
Purity
≥95%
A crystalline solid
DMF: 25 mg/mlDMSO: 10 mg/mlEthanol: 25 mg/mlPBS (pH 7.2): 0.5 mg/ml
λmax
260 nm
SMILES
CC(C(O)=O)C1=CC=C(C(F)=C1)C2=CC=C(O)C=C2
InChi Code
InChI=1S/C15H13FO3/c1-9(15(18)19)11-4-7-13(14(16)8-11)10-2-5-12(17)6-3-10/h2-9,17H,1H3,(H,18,19)
InChi Key
GTSMMBJBNJDFRA-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    4'-hydroxy Flurbiprofen is a major active metabolite of the COX inhibitor flurbiprofen (Item No. 70250) and its enantiomers (R)-flurbiprofen (Item No. 70255) and (S)-flurbiprofen (Item No. 10004207).1 It is formed from flurbiprofen by the cytochrome P450 (CYP) isoform CYP2C9, including CYP2C9 containing an R144C substitution mutation. 4’-hydroxy Flurbiprofen inhibits COX-1 by 94% at a concentration of 1,000 µM but does not inhibit cyclooxygenation of arachidonic acid.2 It completely inhibits cyclooxygenation of 2-arachidonoyl glycerol (2-AG; Item No. 62160) when used at a concentration of 300 µM. 4'-hydroxy Flurbiprofen inhibits fatty acid amide hydrolase (FAAH) hydrolysis of anandamide in rat brain homogenates with an IC50 value of 84 µM at a pH of 6.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tracy, T.S., Marra, C., Wrighton, S.A., et alStudies of flurbiprofen 4'-hydroxylation. Additional evidence suggesting the sole involvement of cytochrome P450 2C9. Biochem. Pharmacol. 52(8), 1305-1309 (1996).

    2. Karlsson, J., and Fowler, C.J. Inhibition of endocannabinoid metabolism by the metabolites of ibuprofen and flurbiprofen. PLoS One 9(7), e103589 (2014).