Niflumic Acid | CAS#4394-00-7

MedKoo Cat#: 318365 | Name: Niflumic Acid

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Description:

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

Niflumic acid is a drug used for joint and muscular pain. It is categorized as an inhibitor of cyclooxygenase-2. In experimental biology, it has been employed to inhibit chloride channels. Niflumic acid has also been reported to act on GABA-A and NMDA channels and to block T-type calcium channels.

Chemical Structure

Niflumic Acid

CAS#4394-00-7

Theoretical Analysis

MedKoo Cat#: 318365

Name: Niflumic Acid

CAS#: 4394-00-7

Chemical Formula: C13H9F3N2O2

Exact Mass: 282.0616

Molecular Weight: 282.22

Elemental Analysis: C, 55.33; H, 3.21; F, 20.20; N, 9.93; O, 11.34

Price and Availability

Size	Price	Availability	Quantity
1g	USD 250.00	2 Weeks
5g	USD 450.00

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Synonym

Niflumic Acid, Donalgin, Flunir, Niflactol, Niflugel, Nifluril

IUPAC/Chemical Name

2-[3-(trifluoromethyl)anilino]pyridine-3-carboxylic acid

InChi Key

JZFPYUNJRRFVQU-UHFFFAOYSA-N

InChi Code

InChI=1S/C13H9F3N2O2/c14-13(15,16)8-3-1-4-9(7-8)18-11-10(12(19)20)5-2-6-17-11/h1-7H,(H,17,18)(H,19,20)

SMILES Code

O=C(C1=CC=CN=C1NC2=CC=CC(C(F)(F)F)=C2)O

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, not in water

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:

Niflumic acid is a Ca2+-activated Cl- channel blocker.

In vitro activity:

The effects of niflumic acid and flufenamic acid, two nonsteroidal anti-inflammatory agents known to block anion transport in red blood cells, on Ca2(+)-activated Cl- currents (ICl(Ca)) in Xenopus oocytes were examined. Both compounds reversibly inhibited ICl(Ca), elicited in response to depolarizing voltage steps, in a dose-dependent manner, with no effect on the shape of the current-voltage curve. The apparent inhibition constant for niflumic acid was 17 microM, whereas that for flufenamic acid was 28 microM. Niflumic acid also inhibited ICl(Ca) elicited by bath application of Ca2+ to oocytes permeabilized using the Ca2+ ionophore A23187, demonstrating that the inhibition of ICl(Ca) is due to a direct interaction with the Cl- channel, rather than by interference with Ca2+ entry through voltage-dependent Ca2+ channels. Reference: Mol Pharmacol. 1990 May;37(5):720-4. https://pubmed.ncbi.nlm.nih.gov/1692608/

In vivo activity:

This study used the steroid-induced rat model of PcP to evaluate inflammation and mucus progression, and tested the effect of niflumic acid (NFA), a fenamate-type drug with potent CLCA1 blocker activity, in decreasing Pneumocystis-associated immunopathology. Administration of NFA caused a significant decrease in total mucus, MUC5AC and mCLCA3 and also, in Pneumocystis-associated inflammation. Most relevant, NFA treatment improved survival at 8 weeks of steroids. Reference: Front Microbiol. 2019 Jul 5;10:1522. https://pubmed.ncbi.nlm.nih.gov/31333624/

	Solvent	mg/mL	mM
Solubility
	DMF	65.0	230.32
	DMSO	57.1	202.17
	Ethanol	33.6	119.09

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 282.22 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.

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. Nakano T, Inoue H, Fukuyama S, Matsumoto K, Matsumura M, Tsuda M, Matsumoto T, Aizawa H, Nakanishi Y. Niflumic acid suppresses interleukin-13-induced asthma phenotypes. Am J Respir Crit Care Med. 2006 Jun 1;173(11):1216-21. doi: 10.1164/rccm.200410-1420OC. Epub 2006 Mar 9. PMID: 16528019. 2. White MM, Aylwin M. Niflumic and flufenamic acids are potent reversible blockers of Ca2(+)-activated Cl- channels in Xenopus oocytes. Mol Pharmacol. 1990 May;37(5):720-4. PMID: 1692608. 3. Pérez FJ, Iturra PA, Ponce CA, Magne F, Garcia-Angulo V, Vargas SL. Niflumic Acid Reverses Airway Mucus Excess and Improves Survival in the Rat Model of Steroid-Induced Pneumocystis Pneumonia. Front Microbiol. 2019 Jul 5;10:1522. doi: 10.3389/fmicb.2019.01522. PMID: 31333624; PMCID: PMC6624676. 4. Marwaha L, Bansal Y, Singh R, Saroj P, Sodhi RK, Kuhad A. Niflumic acid, a TRPV1 channel modulator, ameliorates stavudine-induced neuropathic pain. Inflammopharmacology. 2016 Dec;24(6):319-334. doi: 10.1007/s10787-016-0285-0. Epub 2016 Oct 18. PMID: 27757590.

In vitro protocol:

In vivo protocol:

1. Pérez FJ, Iturra PA, Ponce CA, Magne F, Garcia-Angulo V, Vargas SL. Niflumic Acid Reverses Airway Mucus Excess and Improves Survival in the Rat Model of Steroid-Induced Pneumocystis Pneumonia. Front Microbiol. 2019 Jul 5;10:1522. doi: 10.3389/fmicb.2019.01522. PMID: 31333624; PMCID: PMC6624676. 2. Marwaha L, Bansal Y, Singh R, Saroj P, Sodhi RK, Kuhad A. Niflumic acid, a TRPV1 channel modulator, ameliorates stavudine-induced neuropathic pain. Inflammopharmacology. 2016 Dec;24(6):319-334. doi: 10.1007/s10787-016-0285-0. Epub 2016 Oct 18. PMID: 27757590.

1: Wang K, Ma J, Pang Y, Lao J, Pan X, Tang Q, Zhang F, Su D, Qin S, Shrestha AP. Niflumic Acid Attenuated Pulmonary Artery Tone and Vascular Structural Remodeling of Pulmonary Arterial Hypertension Induced by High Pulmonary Blood Flow In Vivo. J Cardiovasc Pharmacol. 2015 Oct;66(4):383-91. doi: 10.1097/FJC.0000000000000291. PubMed PMID: 26132368. 2: Luo S, Huang G, Wang Z, Wan Z, Chen H, Liao D, Chen C, Li H, Li B, Chen L, Huang Z, He Z. Niflumic acid exhibits anti-tumor activity in nasopharyngeal carcinoma cells through affecting the expression of ERK1/2 and the activity of MMP2 and MMP9. Int J Clin Exp Pathol. 2015 Sep 1;8(9):9990-10001. eCollection 2015. PubMed PMID: 26617707; PubMed Central PMCID: PMC4637792. 3: Radacsi N, Stefanidis GD, Szabó-Révész P, Ambrus R. Analysis of niflumic acid prepared by rapid microwave-assisted evaporation. J Pharm Biomed Anal. 2014 Sep;98:16-21. doi: 10.1016/j.jpba.2014.04.020. Epub 2014 May 9. PubMed PMID: 24873734. 4: Kucherenko YV, Lang F. Niflumic acid affects store-operated Ca(2+)-permeable (SOC) and Ca (2+)-dependent K (+) and Cl (-) ion channels and induces apoptosis in K562 cells. J Membr Biol. 2014 Jul;247(7):627-38. doi: 10.1007/s00232-014-9680-x. Epub 2014 May 25. PubMed PMID: 24858951. 5: Liu W, Zhang W, Si J, Ma K, Li L. [Niflumic acid relaxes mesenteric small artery through downregulating connexin 43 expression in smooth muscle cells from spontaneously hypertensive rat]. Zhonghua Xin Xue Guan Bing Za Zhi. 2014 May;42(5):413-7. Chinese. PubMed PMID: 25042921. 6: Huang LJ, He JB, Wang SJ, Ma YC, Ying L, Wang Y, Wang WT. [The effect of niflumic acid in hypoxic hypercapnia pulmonary vasoconstriction]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2014 Jan;30(1):74-8. Chinese. PubMed PMID: 24741984. 7: Lam WP, Tang HC, Zhang X, Leung PC, Yew DT, Liang W. Low concentrations of niflumic acid enhance basal spontaneous and carbachol-induced contractions of the detrusor. Int Urol Nephrol. 2014 Feb;46(2):349-57. doi: 10.1007/s11255-013-0550-8. Epub 2013 Sep 15. PubMed PMID: 24036984. 8: Cho HY, Park GK, Lee YB. Simultaneous determination of morniflumate and its major active metabolite, niflumic acid, in human plasma by high-performance liquid chromatography in stability and pharmacokinetic studies. Biomed Chromatogr. 2013 Nov;27(11):1438-43. doi: 10.1002/bmc.2940. Epub 2013 May 30. PubMed PMID: 23722315. 9: Takács-Novák K, Szőke V, Völgyi G, Horváth P, Ambrus R, Szabó-Révész P. Biorelevant solubility of poorly soluble drugs: rivaroxaban, furosemide, papaverine and niflumic acid. J Pharm Biomed Anal. 2013 Sep;83:279-85. doi: 10.1016/j.jpba.2013.05.011. Epub 2013 May 18. PubMed PMID: 23770783. 10: Guerrero A, Espinal J, Wood CD, Rendón JM, Carneiro J, Martínez-Mekler G, Darszon A. Niflumic acid disrupts marine spermatozoan chemotaxis without impairing the spatiotemporal detection of chemoattractant gradients. J Cell Sci. 2013 Mar 15;126(Pt 6):1477-87. doi: 10.1242/jcs.121442. Epub 2013 Feb 15. PubMed PMID: 23418354. 11: Ambrus R, Radacsi N, Szunyogh T, van der Heijden AE, Ter Horst JH, Szabó-Révész P. Analysis of submicron-sized niflumic acid crystals prepared by electrospray crystallization. J Pharm Biomed Anal. 2013 Mar 25;76:1-7. doi: 10.1016/j.jpba.2012.12.001. Epub 2012 Dec 10. PubMed PMID: 23287488. 12: Li L, Wang Y, Ma KT, Cheng HJ, Zhao L, Si JQ. [The effect of niflumic acid and blocker of calcium channel on the desensitization of gamma aminobutyric acid-activated current]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2013 Mar;29(2):128-32. Chinese. PubMed PMID: 23833964. 13: Takahashi K, Ishii-Nozawa R, Takeuchi K, Nakazawa K, Sekino Y, Sato K. Niflumic acid activates additional currents of the human glial L-glutamate transporter EAAT1 in a substrate-dependent manner. Biol Pharm Bull. 2013;36(12):1996-2004. PubMed PMID: 24292058. 14: Lim SA, Hwang KY, Chung SH. Niflumic acid reduces histamine-induced interleukin-6 and -8 expression in human conjunctival epithelial cells. Ophthalmic Res. 2013;50(4):192-6. doi: 10.1159/000354177. Epub 2013 Sep 12. PubMed PMID: 24030317. 15: Li L, Li J, Ma KT, Cheng HJ, Zhao L, Wang Y, Si JQ. [The effect of niflumic acid on gamma aminobutyric acid activated current in DRG neurons]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2013 Jan;29(1):68-71. Chinese. PubMed PMID: 23662412. 16: Balderas E, Ateaga-Tlecuitl R, Rivera M, Gomora JC, Darszon A. Niflumic acid blocks native and recombinant T-type channels. J Cell Physiol. 2012 Jun;227(6):2542-55. doi: 10.1002/jcp.22992. PubMed PMID: 21898399; PubMed Central PMCID: PMC4146346. 17: Kondo M, Nakata J, Arai N, Izumo T, Tagaya E, Takeyama K, Tamaoki J, Nagai A. Niflumic acid inhibits goblet cell degranulation in a guinea pig asthma model. Allergol Int. 2012 Mar;61(1):133-42. doi: 10.2332/allergolint.11-OA-0307. PubMed PMID: 22377526. 18: Seo KY, Jeon S, Choi SH, Chung SH. Niflumic Acid Reduces Histamine-Induced MUC5AC Expression in Human Conjunctival Epithelial Cells. Ophthalmic Res. 2011 Oct;46(4):181-6. doi: 10.1159/000325026. Epub 2011 Mar 29. PubMed PMID: 21447991. 19: Kim E, Kang W. Contribution of pH to systemic exposure of niflumic acid following oral administration of talniflumate. Eur J Clin Pharmacol. 2011 Apr;67(4):425-8. doi: 10.1007/s00228-010-0980-5. Epub 2011 Feb 17. PubMed PMID: 21327911. 20: Miners JO, Bowalgaha K, Elliot DJ, Baranczewski P, Knights KM. Characterization of niflumic acid as a selective inhibitor of human liver microsomal UDP-glucuronosyltransferase 1A9: application to the reaction phenotyping of acetaminophen glucuronidation. Drug Metab Dispos. 2011 Apr;39(4):644-52. doi: 10.1124/dmd.110.037036. Epub 2011 Jan 18. PubMed PMID: 21245288.