MedKoo Cat#: 464492 | Name: Flufenamic Acid-d4
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Description:

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

Flufenamic acid-d4 is intended for use as an internal standard for the quantification of flufenamic acid 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). 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. It inhibits calcium influx induced by fMLP or A23187 in human polymorphonuclear leukocytes (PMN) with IC50 values of 29 and 14 µM, respectively. Flufenamic acid also activates various ion channels, including transient receptor potential canonical 6 (TRPC6) and the large-conductance calcium-activated potassium channel (KCa1.1). 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.

Chemical Structure

Flufenamic Acid-d4
Flufenamic Acid-d4
CAS#1185071-99-1

Theoretical Analysis

MedKoo Cat#: 464492

Name: Flufenamic Acid-d4

CAS#: 1185071-99-1

Chemical Formula: C14H6D4F3NO2

Exact Mass: 285.0915

Molecular Weight: 285.26

Elemental Analysis: C, 58.95; H, 4.94; F, 19.98; N, 4.91; O, 11.22

Price and Availability

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1mg USD 550.00 2 Weeks
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Synonym
Flufenamic Acid-d4; Flufenamic Acid d4; FFA-d4; FFA d4; Fluphenamic Acid-d4; Fluphenamic Acid d4;
IUPAC/Chemical Name
2-((3-(trifluoromethyl)phenyl)amino)benzoic-3,4,5,6-d4 acid
InChi Key
LPEPZBJOKDYZAD-ZEJCXXMWSA-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)/i1D,2D,6D,7D
SMILES Code
O=C(O)C1=C([2H])C([2H])=C([2H])C([2H])=C1NC2=CC=CC(C(F)(F)F)=C2
Appearance
Solid powder
Purity
>99% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 285.26 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
1: 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. PMID: 23356979; PMCID: PMC4116821. 2: Fatima R, Sharma M, Prasher P. Targeted delivery of flufenamic acid by V-amylose. Ther Deliv. 2021 Aug;12(8):575-582. doi: 10.4155/tde-2021-0020. Epub 2021 Jun 24. PMID: 34164996. 3: Chen J, Chang Y, Zhu J, Peng Y, Li Z, Zhang K, Zhang Y, Lin C, Lin Z, Pan S, Huang K. Flufenamic acid improves survival and neurologic outcome after successful cardiopulmonary resuscitation in mice. J Neuroinflammation. 2022 Sep 1;19(1):214. doi: 10.1186/s12974-022-02571-2. PMID: 36050694; PMCID: PMC9438280. 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. 5: Sallada N, Li Y, Berger B, Lamm MS. Engineered Hydrophobin as a Crystallization Inhibitor for Flufenamic Acid. ACS Appl Bio Mater. 2021 Aug 16;4(8):6441-6450. doi: 10.1021/acsabm.1c00612. Epub 2021 Jul 26. PMID: 35006868. 6: Alshehri S, Imam SS, Hussain A, Alyousef AM, Altamimi M, Alsulays B, Shakeel F. Flufenamic Acid-Loaded Self-Nanoemulsifying Drug Delivery System for Oral Delivery: From Formulation Statistical Optimization to Preclinical Anti- Inflammatory Assessment. J Oleo Sci. 2020 Oct 7;69(10):1257-1271. doi: 10.5650/jos.ess20070. Epub 2020 Sep 10. PMID: 32908093. 7: Mantas A, Mihranyan A. Dissolution Behavior of Flufenamic Acid in Heated Mixtures with Nanocellulose. Molecules. 2020 Mar 11;25(6):1277. doi: 10.3390/molecules25061277. PMID: 32168901; PMCID: PMC7144018. 8: Rajan KT, Hill AG, Barr A, Whitwell E. Flufenamic acid in rheumatoid arthritis. Ann Rheum Dis. 1967 Jan;26(1):43-6. doi: 10.1136/ard.26.1.43. PMID: 5334569; PMCID: PMC1030997. 9: Mélin L, Abdullayev S, Fnaiche A, Vu V, González Suárez N, Zeng H, Szewczyk MM, Li F, Senisterra G, Allali-Hassani A, Chau I, Dong A, Woo S, Annabi B, Halabelian L, LaPlante SR, Vedadi M, Barsyte-Lovejoy D, Santhakumar V, Gagnon A. Development of LM98, a Small-Molecule TEAD Inhibitor Derived from Flufenamic Acid. ChemMedChem. 2021 Oct 6;16(19):2982-3002. doi: 10.1002/cmdc.202100432. Epub 2021 Jul 28. PMID: 34164919. 10: Kapadia L, Elder MG. Flufenamic acid in treatment of primary spasmodic dysmenorrhoea. A double-blind crossover study. Lancet. 1978 Feb 18;1(8060):348-50. doi: 10.1016/s0140-6736(78)91078-4. PMID: 75392. 11: Kagan G, Huddlestone L, Wolstencroft P. Flufenamic acid and placebo compared in rheumatoid arthritis and osteoarthritis. J Int Med Res. 1981;9(4):253-6. doi: 10.1177/030006058100900403. PMID: 7021261. 12: Pang Y, Buanz A, Gaisford S, Magdysyuk OV, Williams GR. Monitoring Polymorphic Phase Transitions in Flufenamic Acid Amorphous Solid Dispersions Using Hyphenated X-ray Diffraction-Differential Scanning Calorimetry. Mol Pharm. 2022 May 2;19(5):1477-1487. doi: 10.1021/acs.molpharmaceut.2c00016. Epub 2022 Mar 29. PMID: 35347993; PMCID: PMC9097533. 13: 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. PMID: 27131608. 14: Hetmann M, Langner C, Durmaz V, Cespugli M, Köchl K, Krassnigg A, Blaschitz K, Groiss S, Loibner M, Ruau D, Zatloukal K, Gruber K, Steinkellner G, Gruber CC. Identification and validation of fusidic acid and flufenamic acid as inhibitors of SARS-CoV-2 replication using DrugSolver CavitomiX. Sci Rep. 2023 Jul 21;13(1):11783. doi: 10.1038/s41598-023-39071-z. PMID: 37479788; PMCID: PMC10362000. 15: Südhof H. Flufaminsaure [Flufenamic acid]. Dtsch Med Wochenschr. 1968 Dec 13;93(50):2455. German. PMID: 5698984. 16: 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. PMID: 26372652; PMCID: PMC4599580. 17: 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. PMID: 28119077. 18: 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. PMID: 27155725. 19: Gögelein H, Dahlem D, Englert HC, Lang HJ. Flufenamic acid, mefenamic acid and niflumic acid inhibit single nonselective cation channels in the rat exocrine pancreas. FEBS Lett. 1990 Jul 30;268(1):79-82. doi: 10.1016/0014-5793(90)80977-q. PMID: 1696554. 20: Allafchian A, Hosseini H, Ghoreishi SM. Electrospinning of PVA-carboxymethyl cellulose nanofibers for flufenamic acid drug delivery. Int J Biol Macromol. 2020 Nov 15;163:1780-1786. doi: 10.1016/j.ijbiomac.2020.09.129. Epub 2020 Sep 21. PMID: 32971166.