Flunixin meglumine Chemical Properties

Melting point:

136.6-137.4 °C

alpha 

-9～-12゜(D/20℃)(c=12,CH3OH)

storage temp. 

room temp

solubility 

H₂O: freely soluble

form 

solid

color 

off-white

Water Solubility 

soluble

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN 2811 6.1 / PGI

WGK Germany 

3

RTECS 

LZ4367000

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

Flunixin meglumine Usage And Synthesis

Chemical Properties

White Solid

Uses

dental carries prophylactic

Uses

Flunixin meglumine has been used as a nonsteroidal anti-inflammatory drug standard in electrospray ionization mass spectrometry (LC-ESI/MS).

Uses

Cyclooxigenase inhibitor. Anti-inflammatory; analgesic; antipyretic.

Definition

ChEBI: An organoammonium salt obtained by combining flunixin with one molar equivalent of 1-deoxy-1-(methylamino)-D-glucitol. A relatively potent non-narcotic, nonsteroidal analgesic with anti-inflammatory, anti-endotoxic and anti-pyretic propert es; used in veterinary medicine for treatment of horses, cattle and pigs.

brand name

Banamine Veterinary (Schering-Plough Animal Health).

General Description

Flunixin meglumine is a nonsteroidal anti-inflammatory drug and a potent cyclo-oxygenase (COX) inhibitor. It is commonly used as an analgesic and antipyretic in animals.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Biological Activity

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]

Biochem/physiol Actions

COX1, COX2 and PLA2 inhibitor non-narcotic analgesic, anti-pyretic, anti-inflammatory.

Synthesis

Flunixin meglumine is prepared by the reaction of 1-deoxy-1-(methylamino)-D-glucitol and flunixin. The steps are as follows:
Reacting the flunixin with N-methylglucamine in isopropanol, the molar ratio of flunixin to N-methylglucamine is 2:1; fluorine Nisin has a mass ratio to isopropanol of 1:11; and simultaneously added maltodextrin; the molar ratio of the maltodextrin to 2-methyl-3-trifluoromethylaniline is 1:2.5; heating Reflux, filtration, cooling, stirring and crystallization, stirring is continued until the temperature of the system drops below 25 ° C, and the crystals are filtered with suction to obtain flunixin meglumine.

Veterinary Drugs and Treatments

In the United States, flunixin meglumine is approved for use in horses, cattle and swine; however, it is approved for use in dogs in other countries. The approved indications for its use in the horse are for the alleviation of inflammation and pain associated with musculoskeletal disorders and alleviation of visceral pain associated with colic. In cattle it is approved for the control of pyrexia associated with bovine respiratory disease and endotoxemia, and control of inflammation in endotoxemia. In swine, flunixin is approved for use to control pyrexia associated with swine respiratory disease.
Flunixin has been suggested for many other indications in various species, including: Horses: foal diarrheas, shock, colitis, respiratory disease, post-race treatment, and pre- and post ophthalmic and general surgery; Dogs: disk problems, arthritis, heat stroke, diarrhea, shock, ophthalmic inflammatory conditions, pre- and post ophthalmic and general surgery, and treatment of parvovirus infection; Cattle: acute respiratory disease, acute coliform mastitis with endotoxic shock, pain (downer cow), and calf diarrheas; Swine: agalactia/hypogalactia, lameness, and piglet diarrhea. It should be noted that the evidence supporting some of these indications is equivocal and flunixin may not be appropriate for every case.

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]

IC 50

a potent cyclooxygenase inhibitor with ic50 values of 1 nm.

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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