Flufenamic acid

  • CAT Number: A000160
  • CAS Number: 530-78-9
  • Molecular Formula: C14H10F3NO2
  • Molecular Weight: 281.2
  • Purity: ≥95%
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Flufenamic Acid (also known as CI-440, CN-27554, and INF-1837) is a cyclooxygenase inhibitor used to treat inflammation and pain.
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Flufenamic acid is a member of the anthranilic acid derivatives (or fenamate) class of NSAID drugs:718 Like other members of the class, it is a COX inhibitor and prevents formation of prostaglandins. Flufenamic acid is known to bind to and reduce the activity of prostaglandin F synthase and activate TRPC6.
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It is not widely used in humans as it has a high rate (30-60%) of gastrointestinal side effects. It is generally not available in the US. It is available in some Asian and European countries as a generic.
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Scientists led by Claude Winder from Parke-Davis invented flufenamic acid in 1963, along with fellow members of the class, mefenamic acid in 1961 and meclofenamate sodium in 1964.

Catalog Number A000160
CAS Number 530-78-9
Molecular Formula

C14H10F3NO2

Purity 95%
Target COX Inhibitor
Storage -20°C
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)
InChIKey LPEPZBJOKDYZAD-UHFFFAOYSA-N
SMILES C1=CC=C(C(=C1)C(=O)O)NC2=CC=CC(=C2)C(F)(F)F
Reference

1: Guo M, Wang K, Qiao N, Fabian L, Sadiq G, Li M. Insight into Flufenamic Acid
Cocrystal Dissolution in the Presence of a Polymer in Solution: from Single
Crystal to Powder Dissolution. Mol Pharm. 2017 Nov 1. doi:
10.1021/acs.molpharmaceut.7b00712. [Epub ahead of print] PubMed PMID: 29091446.
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2: Smolková R, Zeleňák V, Smolko L, Sabolová D, Kuchár J, Gyepes R. Novel Zn(II)
complexes with non-steroidal anti-inflammatory ligand, flufenamic acid:
Characterization, topoisomerase I inhibition activity, DNA and HSA binding
studies. J Inorg Biochem. 2017 Sep 15;177:143-158. doi:
10.1016/j.jinorgbio.2017.09.005. [Epub ahead of print] PubMed PMID: 28963956.

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3: Ghica MV, Albu Kaya MG, Dinu-P&#238;rvu CE, Lupuleasa D, Udeanu DI. Development,
Optimization and In Vitro/In Vivo Characterization of Collagen-Dextran Spongious
Wound Dressings Loaded with Flufenamic Acid. Molecules. 2017 Sep 15;22(9). pii:
E1552. doi: 10.3390/molecules22091552. PubMed PMID: 28914807.
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4: Alshehri S, Shakeel F, Ibrahim M, Elzayat E, Altamimi M, Shazly G, Mohsin K,
Alkholief M, Alsulays B, Alshetaili A, Alshahrani A, Almalki B, Alanazi F.
Influence of the microwave technology on solid dispersions of mefenamic acid and
flufenamic acid. PLoS One. 2017 Jul 31;12(7):e0182011. doi:
10.1371/journal.pone.0182011. eCollection 2017. PubMed PMID: 28759638; PubMed
Central PMCID: PMC5536357.
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5: Pongkorpsakol P, Yimnual C, Chatsudthipong V, Rukachaisirikul V, Muanprasat C.
Cellular mechanisms underlying the inhibitory effect of flufenamic acid on
chloride secretion in human intestinal epithelial cells. J Pharmacol Sci. 2017
Jun;134(2):93-100. doi: 10.1016/j.jphs.2017.05.009. Epub 2017 Jun 10. PubMed
PMID: 28651800.
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6: Monteillier A, Loucif A, Omoto K, Stevens EB, Lainez S, Saintot PP, Cao L,
Pryde DC. Corrigendum to /Investigation of the structure activity relationship of
flufenamic acid derivatives at the human TRESK channel K2P18.1/ [Bioorg. Med.
Chem. Lett. 26 (2016) 4919-4924]. Bioorg Med Chem Lett. 2017 May 1;27(9):2082.
doi: 10.1016/j.bmcl.2017.02.063. Epub 2017 Mar 17. PubMed PMID: 28320618.
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7: Nechipadappu SK, Tekuri V, Trivedi DR. Pharmaceutical Co-Crystal of Flufenamic
Acid: Synthesis and Characterization of Two Novel Drug-Drug Co-Crystal. J Pharm
Sci. 2017 May;106(5):1384-1390. doi: 10.1016/j.xphs.2017.01.033. Epub 2017 Feb 7.
PubMed PMID: 28185907.
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8: Pongkorpsakol P, Satitsri S, Wongkrasant P, Chittavanich P, Kittayaruksakul S,
Srimanote P, Chatsudthipong V, Muanprasat C. 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.
2017 Mar 5;798:94-104. doi: 10.1016/j.ejphar.2017.01.026. Epub 2017 Jan 21.
PubMed PMID: 28119077.

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9: 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 Oct;163:332-345. doi:
10.1016/j.jinorgbio.2016.04.023. Epub 2016 Apr 22. PubMed PMID: 27155725.
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10: Monteillier A, Loucif A, Omoto K, Stevens EB, Lainez S, 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. Epub 2016 Sep 8. PubMed
PMID: 27641472.

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