An internal standard for the quantification of flufenamic acid
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Unlabeled Version(s)
21447Flufenamic Acid
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Flufenamic Acid-d4

Item No. 33272

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[3-(trifluoromethyl)phenyl]amino]-benzoic acid-d4
CAS Number
1185071-99-1
Synonyms
  • FFA-d4
  • Fluphenamic Acid-d4
Molecular Formula
C14H6D4F3NO2
Formula Weight
285.3
Purity
≥99% deuterated forms (d1-d4)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleMethanol: soluble
SMILES
OC(C(C([2H])=C([2H])C([2H])=C1[2H])=C1NC2=CC(C(F)(F)F)=CC=C2)=OOC(C(C([2H])=C([2H])C([2H])=C1[2H])=C1NC2=CC(C(F)(F)F)=CC=C2)=O
InChi Code
InChI=1S/C14H10F3NO2/c15-14(16,17)9-4-3-5-10(8-9)18-12-7-2-1-6-11(12)13(19)20/h1-8,18H,(H,19,20)/i1D,2D,6D,7D
InChi Key
LPEPZBJOKDYZAD-ZEJCXXMWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Flufenamic acid-d4 is intended for use as an internal standard for the quantification of flufenamic acid (Item No. 21447) by GC- or LC-MS. Flufenamic acid is a non-steroidal anti-inflammatory drug (NSAID) and COX inhibitor (IC50s = 3 and 9.3 µM for human COX-1 and COX-2, respectively).1 Flufenamic acid inhibits TNF-α-induced increases in COX-2 levels and NF-κB activation in HT-29 colon cancer cells in a concentration-dependent manner.2 It inhibits calcium influx induced by fMLP (fMLF; Item No. 21495) or A23187 (Item No. 11016) in human polymorphonuclear leukocytes (PMN) with IC50 values of 29 and 14 µM, respectively.3 Flufenamic acid also activates various ion channels, including transient receptor potential canonical 6 (TRPC6) and the large-conductance calcium-activated potassium channel (KCa1.1).4 It also inhibits various ion channels, including TRPC3 and the cystic fibrosis transmembrane conductance regulator (CFTR). Flufenamic acid (20 mg/kg) reduces increases in intestinal fluid secretion and intestinal barrier disruption in mice infected with the El Tor variant of V. cholerae.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Warner, T.D., Giuliano, F., Vojnovic, I., et al. Nonsteroid drug selectivities for cyclo-oxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: A full in vitro analysis. Proc. Natl. Acad. Sci. USA 96(13), 7563-7568 (1999).

    2. Paik, J.H., Ju, J.H., Lee, J.Y., et al. Two opposing effects of non-steroidal anti-inflammatory drugs on the expression of the inducible cyclooxygenase. Mediation through different signaling pathways. The Journal of Biological Chemisty 275(36), 28173-28179 (2000).

    3. Kankaanranta, H., and Moilanen, E. Flufenamic and tolfenamic acids inhibit calcium influx in human polymorphonuclear leukocytes. Mol. Pharmacol. 47(5), 1006-1013 (1995).

    4. Guinamard, R., Simard, C., and Del Negro, C. Flufenamic acid as an ion channel modulator. Pharmacol. Ther. 138(2), 272-284 (2013).

    5. Pongkorpsakol, P., Satitsri, S., Wongkrasant, P., et al. Flufenamic acid protects against intestinal fluid secretion and barrier leakage in a mouse model of Vibrio cholerae infection through NF-κB inhibition and AMPK activation. Eur. J. Pharmacol. 798, 94-104 (2017).