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Flunixin Meglumin

potent cyclooxygenase inhibitor CAS# 42461-84-7

Flunixin Meglumin

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Chemical structure

Flunixin Meglumin

3D structure

Chemical Properties of Flunixin Meglumin

Cas No. 42461-84-7 SDF Download SDF
PubChem ID 39212 Appearance Powder
Formula C21H28F3N3O7 M.Wt 491.46
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 100 mg/mL (203.48 mM)
H2O : 50 mg/mL (101.74 mM; Need ultrasonic)
*"≥" means soluble, but saturation unknown.
Chemical Name (2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol;2-[2-methyl-3-(trifluoromethyl)anilino]pyridine-3-carboxylic acid
SMILES CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.Cc1c(Nc2ncccc2C(O)=O)cccc1C(F)(F)F
Standard InChIKey MGCCHNLNRBULBU-WZTVWXICSA-N
Standard InChI InChI=1S/C14H11F3N2O2.C7H17NO5/c1-8-10(14(15,16)17)5-2-6-11(8)19-12-9(13(20)21)4-3-7-18-12;1-8-2-4(10)6(12)7(13)5(11)3-9/h2-7H,1H3,(H,18,19)(H,20,21);4-13H,2-3H2,1H3/t;4-,5+,6+,7+/m.0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Flunixin Meglumin

DescriptionFlunixin Meglumine is a potent inhibitor of COX used as analgesic agent with anti-inflammatory and antipyretic activity. Target: COX Flunixin meglumine is a potent, non-narcotic, non-steroidal analgesic agent with anti-inflammatory and antipyretic activity. It is a potent inhibitor of the enzyme cyclooxygenase. Flunixin meglumine therapy significantly (P less than or equal to 0.05) reduced rectal temperatures and quarter signs of inflammation and improved clinically graded depression when compared with these signs in saline solution-treated controls [1]. Flunixin meglumine was selective inhibitor of COX-1. Carprofen inhibited LPS-induction of iNOS. Carprofen and, to a lesser degree, flunixin meglumine had inhibitory effects on NFκB activation [2].

References:
[1]. Anderson, K.L., et al., Efficacy of flunixin meglumine for the treatment of endotoxin-induced bovine mastitis. Am J Vet Res, 1986. 47(6): p. 1366-72. [2]. Bryant, C.E., B.A. Farnfield, and H.J. Janicke, Evaluation of the ability of carprofen and flunixin meglumine to inhibit activation of nuclear factor kappa B. Am J Vet Res, 2003. 64(2): p. 211-5.

Flunixin Meglumin Dilution Calculator

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Preparing Stock Solutions of Flunixin Meglumin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.0348 mL 10.1738 mL 20.3475 mL 40.6951 mL 50.8688 mL
5 mM 0.407 mL 2.0348 mL 4.0695 mL 8.139 mL 10.1738 mL
10 mM 0.2035 mL 1.0174 mL 2.0348 mL 4.0695 mL 5.0869 mL
50 mM 0.0407 mL 0.2035 mL 0.407 mL 0.8139 mL 1.0174 mL
100 mM 0.0203 mL 0.1017 mL 0.2035 mL 0.407 mL 0.5087 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Flunixin Meglumin

IC50: A potent cyclooxygenase inhibitor with IC50 values of 1 nM.

Flunixin meglumine serves as a non-narcotic and non-steroidal analgesic agent with antipyretic activities. As a potent inhibitor of the enzyme cyclooxygenase, Flunixin meglumine has demonstrated a wide-spectrum of biological activities including anti-inflammation and pain-alleviating. Moreover, Flunixin meglumine could be applied as a drug in animals for the management of intestinal ischaemia, colic, and endotoxemia. [1]

In vitro: An in vitro whole blood model in feedlot calves was adopted to detect the activity of the anti-inflammatory agents Flunixin-meglumine (FLU), RS (±) Carprofen (CPF) and S (+) CPF. The drugs all exhibited inhibitory activity on COXs, with an order of FLU > S (+) CPF > RS (±) CPF in their potency. This finding indicated that FLU was a nonselective suppressorr of bovine COXs, whereas RS (±) CPF and S (+) CPF selectively inhibited COX-2 isoenzyme. [2]

In vivo: Findings from mice, rats and monkeys suggested Flunixin meglumine as a potent non-narcotic analgesic agent after parenteral administration. After being subcutaneous administered, this agent showed higher efficacy than pentazocine, meperidine and codeine in the rat yeast paw test. Intramuscular administration and subcutaneous administration of Flunixin meglumine had similar effects. Moreover, orally administered Flunixin meglumine also exerted analgesic and anti-inflammatory activities. Based on mice abdominal constriction test, flunixin meglumine had comparable efficacy to pentazocine and was more potent than meperidine and codeine. In primates, 10 mg/kg flunixin meglumine showed an equal efficacy to that of 0.3 mg/kg morphine. [1]

Clinical trials: Flunixin meglumine, in a dosage of 1.0 mg/kg bwt, was studied in a blind Multi-Centre clinical trial in 152 horses with abdominal pain. Significant differences were noted in kicking, pawing, head and body movement and attitude between the horses receiving flunixin meglumine and control. Moreover, compared with detomidin, Flunixin meglumine provided significantly less analgesia. [3]

References:
[1]Ciofalo VB, Latranyi MB, Patel JB and Taber RI.  Flunixin meglumine: a non-narcotic analgesic. J Pharmacol Exp Ther. 1977 Mar; 200(3): 501-7.
[2]Miciletta M, Cuniberti B, Barbero R and Re G.  In vitro enantioselective pharmacodynamics of Carprofen and Flunixin-meglumine in feedlot cattle. J Vet Pharmacol Ther. 2014 Feb; 37(1): 43-52.
[3] Jochle W, Moore JN, Brown J, Baker GJ, Lowe JE, Fubini S, Reeves MJ, Watkins JP and White NA.  Comparison of detomidine, butorphanol, flunixin meglumine and xylazine in clinical cases of equine colic. Equine Vet J Suppl. 1989 Jun; (7): 111-6.

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References on Flunixin Meglumin

Possible active transport mechanism in pharmacokinetics of flunixin-meglumin in rabbits.[Pubmed:11558544]

J Vet Med Sci. 2001 Aug;63(8):885-8.

The plasma and urine kinetics of flunixin-meglumin (FNX, 2 mg/kg, i.v.) in rabbits were examined. Unusual pharmacokinetic profiles were obtained, including high binding percentage with plasma protein (> 99%), a short elimination half-life (< 4 hr) and a relatively large Vd-area (0.5 L/kg). These profiles indicate that some active transport mechanisms are involved in FNX disposition. The recovery of FNX from urine was approximately 9 % of the dose within 24 hr following the injection. The estimated renal clearance of the unbound drug nearly corresponded to the renal blood flow rates, indicating that active tubular secretion in the renal re-absorptive tract may be involved in the disposition. The effect of a concomitant administration of pravastatin (PV) on FNX disposition was also examined. PV is a representative substrate of a transporter in human liver cells (OATP-2). After the PV administrations, the Vd-area of FNX and total body clearance markedly decreased, indicating that FNX is actively taken up and metabolized in liver cells by an OATP-2 like transporter. In conclusion, there are at least 2 active transport pathways for FNX pharmacokinetics in rabbits, one is renal tubular secretion and the other is in the sinusoidal section of the liver.

Hepatic effects of flunixin-meglumin in LPS-induced sepsis.[Pubmed:20030736]

Fundam Clin Pharmacol. 2010 Dec;24(6):759-69.

The aim of this study was to evaluate the actions of the non-steroidal anti-inflammatory drug flunixin-meglumin (FM) on the changes caused by lipopolysaccharide (LPS)-induced sepsis in the rat liver. Eight groups of five adult male Wistar rats were analysed: (1) saline injected (controls), (2) FM treated with 1.1 mg/kg, (3) FM treated with 2.2 mg/kg, (4) LPS-injected (10 mg/kg), (5) LPS-injected with 1.1 mg/kg FM pretreatment, (6) LPS-injected with 2.2 mg/kg FM pretreatment, (7) LPS-injected with 1.1 mg/kg FM post-treatment and (8) LPS-injected with 2.2 mg/kg FM post-treatment. All drugs were intraperitoneally injected. The following parameters were evaluated: plasma levels of hepatic enzymes and urea, hepatic histological characteristics, antioxidant enzymes and several metabolic fluxes. The latter comprised gluconeogenesis, ureagenesis and oxygen consumption. Liver damage in LPS-induced sepsis was characterized by histological changes, increased plasma levels of alanine aminotransferase and aspartate aminotransferase (P < 0.001) and diminished gluconeogenesis (P < 0.001) and ureagenesis (P < 0.01). LPS also induced oxidative stress as evidenced by increased catalase (P < 0.05) and superoxide dismutase activities and enhanced lipid peroxidation (P < 0.001). Pretreatment of the animals with FM minimized the histological changes and normalized, in part, all enzymatic activities. Pretreatment of the animals with FM also normalized gluconeogenesis and partly restored ureagenesis (P < 0.05). These and other results show that LPS-induced sepsis may lead to severe liver damage, affecting both structure and function. Treatment with FM can be used to avoid this damage. The antioxidant properties of FM can be, partly at least, responsible for this protective action.

Description

Flunixin Meglumine is a potent inhibitor of COX used as analgesic agent with anti-inflammatory and antipyretic activity.

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