[CAS NO. 91-40-7] Fenamic acid
PRODUCTS SPECIFICATIONS [91-40-7]
DESCRIPTION [91-40-7]
Overview
| MDL | MFCD00002421 |
|---|---|
| Molecular Weight | 213.23 |
| Molecular Formula | C13H11NO2 |
| SMILES | O=C(O)C1=CC=CC=C1NC2=CC=CC=C2 |
Summary
Fenamic acid (N-Phenylanthranilic acid, NPAA) is an orally active chloride channel blocker. Fenamic acid is the basic constituent of non-steroidal anti-inflammatory agents (NSAIA), and derives into mefenamic, tofenacin, flufenac acid and melofenac acid. Fenamic acid also acts as antibacterial and analgesic agent [1] - [6] .
IC50 & Target
Chloride Channel [1]
In Vitro
Fenamic acid (N-Phenylanthranilic acid, NPAA) (2.5 mM; 3 h) inhibits Cl
-
transportation and blocks
36
C1
-
uptake and efflux in endothelial cells
[1]
[2]
.
Fenamic acid exhibits selectivity to AKR1B10 (the tumor-marker) over human AR, and inhibits AKR1B10 with IC
50
s of 0.76 μM (Flufenamic acid), 1.6 μM (Mefenamic acid), 9.89 μM (Meclofenamic acid), respectively
[4]
.
Fenamic acid (4-16 µg/mL; 72 h) inhibits 50% of
Neisseria gonorrhoeae
with an MIC
50
value from 4 to 16 µg/mL (tolfenamic acid, flufenamic acid, and meclofenamic acid) in a low frequency of resistance
[5]
.
Fenamic acid (2-8 µg/mL; 8 h) reduces the expression of the porinflammatory cytokines (IL-8, IL-6 and IL-ß) by infected endocervical cells without (>128 µg/mL; 24 h) inhibition towards commensal
Lactobacillus
spp. belonging healthy female genital microbiota
[5]
.
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
RPA-1 is a biomarker in the detection of collecting duct injury in papillary necrosis in male rats
[3]
.
Fenamic acid (N-Phenylanthranilic acid, NPAA) (350-700 mg/kg/day; o.p.; 4 d, 8 d, and 15 d) causes renal papillary necrosis and increases urinary renal papillary antigen-1 (RPA-1) in rats
[3]
.
Fenamic acid (20 g/0.2 mL; i.p.) shows inhibitory effect against the abdominal constriction induced by acetic acid in mice
[6]
.
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
| Animal Model: | Male Wistar Hannover rats (8-10 weeks old; weighting 220-270 g) [3] |
| Dosage: | 50, 350, or up to 700 mg/kg |
| Administration: | Oral gavage; once daily; 7 days or 14 days |
| Result: |
Increased absolute paired kidney weights (13.8% at 350 mg/kg and 21.2% at 700/500 mg/kg) and relative to body weight (10.5% at 350 mg/kg/day and 20.3% at 700/500 mg/kg/day).
Caused minimal papillary necrosis of tip with necrosis, hemorrhage, and inflammation of collecting ducts. |
| Animal Model: | Male NMRI mice (weighting 20-25 g); abdominal constriction model (writhing test), induced by acetic acid [6] |
| Dosage: | 100 g/mL, each mice injected with 20 mL |
| Administration: | Intraperitoneal injection; once |
| Result: | Showed anti-nociceptive activity and inhibited the abdominal constriction with the maximal inhibition of 96.3% (Mefenamic acid). |
Appearance
Solid
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
4°C, protect from light
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
Solvent & Solubility
DMSO : 125 mg/mL ( 586.22 mM ; Need ultrasonic)
H 2 O : < 0.1 mg/mL (ultrasonic;warming;heat to 60°C) (insoluble)
Stock Solutions
| Concentration Solvent Mass | 1 mg | 5 mg | 10 mg |
|---|
| 1 mM | 4.6898 mL | 23.4489 mL | 46.8977 mL |
| 5 mM | 0.9380 mL | 4.6898 mL | 9.3795 mL |
| 10 mM | 0.4690 mL | 2.3449 mL | 4.6898 mL |
-
1.
References
- [1] Mandel KG, et al. Characterization of a cyclic AMP-activated Cl-transport pathway in the apical membrane of a human colonic epithelial cell line. J Biol Chem. 1986 Jan 15. 261(2):704-12.
- [2] Ueda S, et al. Chloride efflux in cyclic AMP-induced configurational change of bovine pulmonary artery endothelial cells. Circ Res. 1990 Apr. 66(4):957-67.
- [3] Betton GR, et, al. Biomarkers of collecting duct injury in Han-Wistar and Sprague-Dawley rats treated with N-phenylanthranilic Acid. Toxicol Pathol. 2012 Jun;40(4):682-94.
- [4] Endo S, et al. Selective inhibition of the tumor marker AKR1B10 by antiinflammatory N-phenylanthranilic acids and glycyrrhetic acid. Biol Pharm Bull. 2010. 33(5):886-90.
- [5] Seong YJ, et al. Repurposing Fenamic Acid Drugs To Combat Multidrug-Resistant Neisseria gonorrhoeae. Antimicrob Agents Chemother. 2020 Jun 23. 64(7):e02206-19.
- [6] Almasirad A, et al. Synthesis and analgesic activity of 2-phenoxybenzoic acid and N-phenylanthranilic acid hydrazides. Biol Pharm Bull. 2006 Jun. 29(6):1180-5.
Synonyms