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MedKoo Cat#: 328901 | Name: Flufenamic Acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Flufenamic Acid (also known as CI-440, CN-27554, and INF-1837) is a cyclooxygenase inhibitor used to treat inflammation and pain.

Chemical Structure

Flufenamic Acid
Flufenamic Acid
CAS#530-78-9 (free acid)

Theoretical Analysis

MedKoo Cat#: 328901

Name: Flufenamic Acid

CAS#: 530-78-9 (free acid)

Chemical Formula: C14H10F3NO2

Exact Mass: 281.0664

Molecular Weight: 281.23

Elemental Analysis: C, 59.79; H, 3.58; F, 20.27; N, 4.98; O, 11.38

Price and Availability

Size Price Availability Quantity
10g USD 250.00 2 Weeks
25g USD 450.00 2 Weeks
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Related CAS #
21951-45-1 16449-54-0 (aluminum) 530-78-9 (free acid)
Synonym
Flufenamic Acid; CI-440; CN-27554; INF-1837; CI 440; CN 27554; INF 1837; CI440; CN27554; INF1837
IUPAC/Chemical Name
2-((3-(trifluoromethyl)phenyl)amino)benzoic acid
InChi Key
LPEPZBJOKDYZAD-UHFFFAOYSA-N
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)
SMILES Code
O=C(O)C1=CC=CC=C1NC2=CC=CC(C(F)(F)F)=C2
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Flufenamic acid is a non-steroidal anti-inflammatory agent, inhibits cyclooxygenase (COX), activates AMPK, and also modulates ion channels, blocking chloride channels and L-type Ca2+ channels, modulating non-selective cation channels (NSC), activating K+ channels.
In vitro activity:
Oil red O staining and quantification indicated that 12.5, 25, 50, 100, and 200 μM FFA (flufenamic acid) had an inhibitory effect on the adipogenic differentiation of hASCs cultured in AM on day 21 (Figures 1(a) and 1(b)). Meanwhile, qRT-PCR showed that 12.5, 25, 50, and 100 μM FFA significantly attenuated the expression of PPARG (Figure 1(c)) and CEBPA (Figure 1(d)) at day 14, whereas FFA at 200 μM did not. Reference: Stem Cells Int. 2020; 2020: 1540905. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7102471/
In vivo activity:
The inflammatory response was obviously enhanced in CLP-constructed sepsis rats and alleviated by FFA (flufenamic acid) treatment. Sepsis induced the increase of W/D ratio, promoted the levels of TNF-α, IL-6, HMGBR1, and MDA and inhibited the levels of SOD and GSH. FFA could effectively alleviate the sepsis-induced lung injury. Reference: Drug Dev Res. 2020 Nov;81(7):885-892. https://pubmed.ncbi.nlm.nih.gov/32542754/
Solvent mg/mL mM
Solubility
DMF 59.0 209.79
Ethanol 31.7 112.75
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 281.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Liu X, Li Z, Liu H, Zhu Y, Xia D, Wang S, Gu R, Zhang P, Liu Y, Zhou Y. Flufenamic Acid Inhibits Adipogenic Differentiation of Mesenchymal Stem Cells by Antagonizing the PI3K/AKT Signaling Pathway. Stem Cells Int. 2020 Mar 16;2020:1540905. doi: 10.1155/2020/1540905. PMID: 32256607; PMCID: PMC7102471. 2. Ge R, Hu L, Tai Y, Xue F, Yuan L, Wei G, Wang Y. Flufenamic acid promotes angiogenesis through AMPK activation. Int J Oncol. 2013 Jun;42(6):1945-50. doi: 10.3892/ijo.2013.1891. Epub 2013 Apr 10. PMID: 23589027. 3. Jiang Q, Chen Z, Jiang H. Flufenamic acid alleviates sepsis-induced lung injury by up-regulating CBR1. Drug Dev Res. 2020 Nov;81(7):885-892. doi: 10.1002/ddr.21706. Epub 2020 Jun 16. PMID: 32542754. 4. Zhang S, Huo S, Li H, Tang H, Nie B, Qu X, Yue B. Flufenamic acid inhibits osteoclast formation and bone resorption and act against estrogen-dependent bone loss in mice. Int Immunopharmacol. 2020 Jan;78:106014. doi: 10.1016/j.intimp.2019.106014. Epub 2019 Nov 24. PMID: 31776093.
In vitro protocol:
1. Liu X, Li Z, Liu H, Zhu Y, Xia D, Wang S, Gu R, Zhang P, Liu Y, Zhou Y. Flufenamic Acid Inhibits Adipogenic Differentiation of Mesenchymal Stem Cells by Antagonizing the PI3K/AKT Signaling Pathway. Stem Cells Int. 2020 Mar 16;2020:1540905. doi: 10.1155/2020/1540905. PMID: 32256607; PMCID: PMC7102471. 2. Ge R, Hu L, Tai Y, Xue F, Yuan L, Wei G, Wang Y. Flufenamic acid promotes angiogenesis through AMPK activation. Int J Oncol. 2013 Jun;42(6):1945-50. doi: 10.3892/ijo.2013.1891. Epub 2013 Apr 10. PMID: 23589027.
In vivo protocol:
1. Jiang Q, Chen Z, Jiang H. Flufenamic acid alleviates sepsis-induced lung injury by up-regulating CBR1. Drug Dev Res. 2020 Nov;81(7):885-892. doi: 10.1002/ddr.21706. Epub 2020 Jun 16. PMID: 32542754. 2. Zhang S, Huo S, Li H, Tang H, Nie B, Qu X, Yue B. Flufenamic acid inhibits osteoclast formation and bone resorption and act against estrogen-dependent bone loss in mice. Int Immunopharmacol. 2020 Jan;78:106014. doi: 10.1016/j.intimp.2019.106014. Epub 2019 Nov 24. PMID: 31776093.
1: Hendriks CM, Penning TM, Zang T, Wiemuth D, Gründer S, Sanhueza IA, Schoenebeck F, Bolm C. Pentafluorosulfanyl-containing flufenamic acid analogs: Syntheses, properties and biological activities. Bioorg Med Chem Lett. 2015 Oct 15;25(20):4437-40. doi: 10.1016/j.bmcl.2015.09.012. Epub 2015 Sep 8. PubMed PMID: 26372652; PubMed Central PMCID: PMC4599580. 2: Hoppel M, Ettl H, Holper E, Valenta C. Influence of the composition of monoacyl phosphatidylcholine based microemulsions on the dermal delivery of flufenamic acid. Int J Pharm. 2014 Nov 20;475(1-2):156-62. doi: 10.1016/j.ijpharm.2014.08.058. Epub 2014 Aug 29. PubMed PMID: 25178824. 3: Mahrhauser DS, Kählig H, Partyka-Jankowska E, Peterlik H, Binder L, Kwizda K, Valenta C. Investigation of microemulsion microstructure and its impact on skin delivery of flufenamic acid. Int J Pharm. 2015 Jul 25;490(1-2):292-7. doi: 10.1016/j.ijpharm.2015.05.056. Epub 2015 May 26. PubMed PMID: 26022888. 4: Hoppel M, Juric S, Ettl H, Valenta C. Effect of monoacyl phosphatidylcholine content on the formation of microemulsions and the dermal delivery of flufenamic acid. Int J Pharm. 2015 Feb 1;479(1):70-6. doi: 10.1016/j.ijpharm.2014.12.048. Epub 2014 Dec 24. PubMed PMID: 25542986. 5: Bencze M, Behuliak M, Vavřínová A, Zicha J. Broad-range TRP channel inhibitors (2-APB, flufenamic acid, SKF-96365) affect differently contraction of resistance and conduit femoral arteries of rat. Eur J Pharmacol. 2015 Oct 15;765:533-40. doi: 10.1016/j.ejphar.2015.09.014. Epub 2015 Sep 16. PubMed PMID: 26384458. 6: Delaney SP, Korter TM. Terahertz spectroscopy and computational investigation of the flufenamic acid/nicotinamide cocrystal. J Phys Chem A. 2015 Apr 2;119(13):3269-76. doi: 10.1021/jp5125519. Epub 2015 Mar 23. PubMed PMID: 25787318. 7: Guinamard R, Simard C, Del Negro C. Flufenamic acid as an ion channel modulator. Pharmacol Ther. 2013 May;138(2):272-84. doi: 10.1016/j.pharmthera.2013.01.012. Epub 2013 Jan 25. Review. PubMed PMID: 23356979; PubMed Central PMCID: PMC4116821. 8: Guo M, Wang K, Hamill N, Lorimer K, Li M. Investigating the Influence of Polymers on Supersaturated Flufenamic Acid Cocrystal Solutions. Mol Pharm. 2016 Sep 6;13(9):3292-307. doi: 10.1021/acs.molpharmaceut.6b00612. Epub 2016 Aug 15. PubMed PMID: 27494289. 9: Chavez-Dozal AA, Jahng M, Rane HS, Asare K, Kulkarny VV, Bernardo SM, Lee SA. In vitro analysis of flufenamic acid activity against Candida albicans biofilms. Int J Antimicrob Agents. 2014 Jan;43(1):86-91. doi: 10.1016/j.ijantimicag.2013.08.018. Epub 2013 Oct 1. PubMed PMID: 24156913; PubMed Central PMCID: PMC3902125. 10: Pyatski Y, Zhang Q, Mendelsohn R, Flach CR. Effects of permeation enhancers on flufenamic acid delivery in Ex vivo human skin by confocal Raman microscopy. Int J Pharm. 2016 May 30;505(1-2):319-28. doi: 10.1016/j.ijpharm.2016.04.011. Epub 2016 Apr 6. PubMed PMID: 27063850. 11: Tarushi A, Kastanias P, Raptopoulou CP, Psycharis V, Kessissoglou DP, Papadopoulos AN, Psomas G. Zinc complexes of flufenamic acid: Characterization and biological evaluation. J Inorg Biochem. 2016 Apr 22. pii: S0162-0134(16)30108-8. doi: 10.1016/j.jinorgbio.2016.04.023. [Epub ahead of print] PubMed PMID: 27155725. 12: Malinovskaja-Gomez K, Labouta HI, Schneider M, Hirvonen J, Laaksonen T. Transdermal iontophoresis of flufenamic acid loaded PLGA nanoparticles. Eur J Pharm Sci. 2016 Jun 30;89:154-62. doi: 10.1016/j.ejps.2016.04.034. Epub 2016 Apr 27. PubMed PMID: 27131608. 13: Bal R, Ustundag Y, Bulut F, Demir CF, Bal A. Flufenamic acid prevents behavioral manifestations of salicylate-induced tinnitus in the rat. Arch Med Sci. 2016 Feb 1;12(1):208-15. doi: 10.5114/aoms.2016.57597. Epub 2016 Feb 2. PubMed PMID: 26925138; PubMed Central PMCID: PMC4754382. 14: Monteillier A, Loucif A, Omoto K, Stevens EB, Vicente SL, Saintot PP, Cao L, Pryde DC. Investigation of the structure activity relationship of flufenamic acid derivatives at the human TRESK channel K(2P)18.1. Bioorg Med Chem Lett. 2016 Oct 15;26(20):4919-4924. doi: 10.1016/j.bmcl.2016.09.020. PubMed PMID: 27641472. 15: Tolia C, Papadopoulos AN, Raptopoulou CP, Psycharis V, Garino C, Salassa L, Psomas G. Copper(II) interacting with the non-steroidal antiinflammatory drug flufenamic acid: structure, antioxidant activity and binding to DNA and albumins. J Inorg Biochem. 2013 Jun;123:53-65. doi: 10.1016/j.jinorgbio.2013.02.009. Epub 2013 Feb 28. PubMed PMID: 23528572.

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