Basic information Animal-specific antibacterial drugs Uses Safety Related Supplier
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Basic information Animal-specific antibacterial drugs Uses Safety Related Supplier
Flumequine Basic information
Flumequine Chemical Properties
  • Melting point:253-255°C
  • Boiling point:439.7±45.0 °C(Predicted)
  • Density 1.45±0.1 g/cm3(Predicted)
  • RTECS DK1672000
  • Flash point:>110°(230°F)
  • storage temp.  0-6°C
  • solubility 1 M NH4OH: soluble50mg/mL
  • pkapKa 6.42(H2O t=25.0 I=0.025)(Approximate)
  • form powder
  • color white to off-white
  • Water Solubility Soluble in DMSO and dilute alkali hydroxides. Insoluble in water
  • Merck 14,4137
  • BRN 490724
  • Stability:Stable. Incompatible with strong oxidizing agents.
  • CAS DataBase Reference42835-25-6(CAS DataBase Reference)
  • EPA Substance Registry System1H,5H-Benzo[ij]quinolizine-2-carboxylic acid, 9-fluoro-6,7-dihydro-5-methyl-1-oxo- (42835-25-6)
Safety Information
Flumequine Usage And Synthesis
  • Animal-specific antibacterial drugsIt appears as white powder and is odorless and tasteless. It is insoluble in water but is immiscible with organic solvent.
    Flumequine is a kind of synthetic second-generation, animal-specific quinolone antibacterial drugs. It is currently the only non-humans shared broad-spectrum antimicrobial veterinary drug. It is taken as the substitute product of norfloxacin. It has a strong bactericidal activity with excellent efficacy in the treatment of animal bacterial diseases. Its main effect is to inhibit bacterial deoxy nucleic acid (DNA) gyrase, interfering with the deoxyribonucleic acid (DNA) synthesis, thereby causing failure of cell for further division, and thus playing the role of killing bacteria. It is mainly used in animal bacterial respiratory disease including E. coli, dysentery, salmonellosis, typhoid, fowl cholera, staphylococcal disease and infectious rhinitis. It can also be used for the treatment of E. coli disease, monospora disease and Vibrio disease in aquatic animals with strong inhibitory effect on the Aeromonas hydrophila.
    Flumequine was first successfully developed by the Rinker laboratory and had been successively and widely used in the EU and Japan and other countries in livestock and aquaculture since 1970s with excellent efficacy in the treatment of various kinds of diseases caused by Gram-negative infections, especially for the treatment of livestock, poultry and aquatic animal diseases caused by Escherichia coli, mycoplasma, and Aeromonas hydrophila. It had been gradually developed and approved to enter into market by our country in the late 1990s and mainly used for the control of bacterial infection diseases of salmon, trout, shrimp, eel and pigs as well as chickens.
    Since quinolones-class sodium flumequine can inhibit bacterial DNA gyrase and has a broad spectrum antibiotic, high efficiency, low toxicity and strong tissue penetration capability with no anesthesia effect, it has become one of the most important anti-infective drugs in veterinary clinical diagnosis and aquaculture and has been used extensively for the treatment, prevention and promoting growth. Because of its resistance and potential carcinogenicity, the European Union, Japan and China have all provided their maximal residue limit in the tissue (our country and the European Union both use the value of 100ppb). The current methods of detecting flumequine mainly include fluorescent spectrophotometry, enzyme-linked assay (ELISA) and liquid chromatography. ELISA, with its high sensitivity and easy operation, has become routine screening methods.
    This information is edited by Xiongfeng Dai from Chemicalbook.
  • UsesIt is a kind of newly synthetic broad-spectrum antimicrobial drugs with excellent efficacy in the treatment of animal bacterial diseases.
    It can be used as pharmaceutical raw material.
  • Chemical PropertiesWhite Crystalline Solid
  • OriginatorApurone,Riker,France,1977
  • Usesvasodilator
  • UsesFluorinated quinolone antibacterial
  • Manufacturing Process6-Fluoro-2-methyltetrahydroquinoline (32.2 g, 0.2 mol) is mixed with diethyl ethoxymethylenemalonate, and the mixture is heated at 125°C to 130°C for 3 hours. Polyphosphoric acid (200 g) is added, and the solution is gradually heated to 115°C to 120°C in an oil bath with occasional stirring. The temperature is maintained for 1 hour, then the mixture is poured into 600 ml of water and neutralized with 40% sodium hydroxide solution. The product ester which precipitates is separated by filtration, washed with water and suspended in 2 liters of 10% sodium hydroxide solution. The mixture is heated on the steam bath for 1 hour, treated with decolorizing charcoal, filtered, then neutralized with concentrated hydrochloric acid. The solid product is isolated by filtration of the hot solution, washed with water and recrystallized from dimethylformamide.
  • Therapeutic FunctionAntibacterial
  • Pharmaceutical ApplicationsA tricyclic fluorinated 4-quinolone, with activity similar to that of nalidixic acid in vitro, although it is somewhat more active against some Enterobacteriaceae.
    Following escalating oral doses of 400, 800 or 1200 mg, mean peak plasma levels reached at 2 h are 13.5, 23.8 and 31.9 mg/L, respectively. The apparent elimination half-life is about 7 h. The main metabolite, hydroxyflumequine, is much more rapidly eliminated. About 60% of a dose appears in the urine, mostly in the form of conjugates. Urinary concentrations following an 800 mg dose are 10–35 mg/L, with a peak of 105 mg/L. It has no effect on the pharmacokinetics of theophylline.
    Flumequine is generally well tolerated, side effects being mainly mild gastrointestinal tract disturbances, rashes, dizziness and confusion.
    It is principally used in uncomplicated urinary tract infections.
Flumequine(42835-25-6)Related Product Information
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