Name | flumequine |
Synonyms | FLUMEQUIN flumequine FLUMEQUINE Fluoromethyl Flumequine solution Fluoromethylquinoline FLUMEQUINE PESTANAL, 250 MG FLUMEQUINE STANDARD SOLUTION 9-fluoro-6,7-dihydro-5-methyl-1-oxo-1h,5h-benzo[ij]quinolizine-2-carboxylic acid 9-Fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid 9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid |
CAS | 42835-25-6 |
EINECS | 255-962-6 |
InChI | InChI=1/C14H12FNO3/c1-7-2-3-8-4-9(15)5-10-12(8)16(7)6-11(13(10)17)14(18)19/h4-7H,2-3H2,1H3,(H,18,19) |
Molecular Formula | C14H12FNO3 |
Molar Mass | 261.25 |
Density | 1.45±0.1 g/cm3(Predicted) |
Melting Point | 253-255°C |
Boling Point | 439.7±45.0 °C(Predicted) |
Flash Point | >110°(230°F) |
Water Solubility | Soluble in DMSO and dilute alkali hydroxides. Insoluble in water |
Solubility | DMSO 3 mg/mL, water <1 mg/mL, ethanol <1 mg/mL |
Vapor Presure | 1.66E-08mmHg at 25°C |
Appearance | white to off-white(powder) |
Color | white to off-white |
Merck | 14,4137 |
BRN | 490724 |
pKa | pKa 6.42(H2O t=25.0 I=0.025)(Approximate) |
Storage Condition | Sealed in dry,Store in freezer, under -20°C |
Stability | Stable. Incompatible with strong oxidizing agents. |
Refractive Index | 1.645 |
MDL | MFCD00079298 |
Physical and Chemical Properties | This product is a white powder, odorless, tasteless, insoluble in water and miscible in organic solvents. Packaging specifications: paper barrel, two layers of plastic bags, 40CM in diameter, 50CM high. This product is non-toxic, non-anesthetic, not flammable and explosive. |
Use | Is a new broad-spectrum antibacterial synthetic drugs, animal bacterial diseases have good curative effect |
In vitro study | Flumequine inhibits eukaryote topoisomerase II, which is responsible for the double-strand DNA break reaction and bacterial helicase being affected, the inhibitory effect of FL on topoisomerase II was highly correlated with the effect on bacterial helicase. The minimum inhibitory concentration of Flumequine ranged from 0.06 μg/ml to 32 μg/ml for 12 clinical A. salmonicida strains. Flumequine has a high E(max) value of 16 for most resistant strains, which is an important contribution to the elimination of the resistant phenotype. The Flumequine accumulation test confirmed that high E(max) values were associated with very low levels of accumulation. |
In vivo study | Flumequine (4000 ppm, oral) induced dose-dependent DNA damage in the stomach, colon, and bladder of adult mice 3, but not 24 hours after administration. Flumequine showed 44.7% bioavailability in Atlantic salmon after consumption of medicated feed. After intravenous administration of Atlantic salmon, the apparent volume of distribution of Flumequine is stable at 3.5 liters/kg, and the elimination half-life (t 1/2) is 22.8 hours, the area under the plasma drug concentration time curve (ACC) was 140 μg x h/ml. In the water grass Lythrum salicaria L, Flumequine (100 mg/L) reduced the average length of roots, hypocotyls and cotyledons, and reduced the number of secondary roots. After intravenous administration, Flumequine (10 mg/kg, oral) had a constant apparent volume of distribution (Vss) of 2.41 L/kg (COD) and 2.15 L/kg (Wrasse).. After administration of Flumequine (10 mg/kg, P. O.), the total clearance (Cl) was 0.024 L/h. KG (COD),0.14 L/h. KG (Wrasse), elimination half-life (t1/2λz) was 75 H (COD),31 H (Wrasse). After oral administration of Flumequine, the oral bioavailability (F) was 65% (COD) and 41% (Wrasse). |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S27 - Take off immediately all contaminated clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
WGK Germany | 3 |
RTECS | DK1672000 |
FLUKA BRAND F CODES | 10 |
HS Code | 29339900 |
Reference Show more | 1. Liu Weihua, Yu Wenlong, Yang Qian, et al. Colloidal gold-labeled immune solid-phase membrane detection of flumequine in animal foods [J]. Food Research and Development, 2020(5). 2. Liu Weihua et al. [IF = 3.366]. "Study on a biological essence-Linked immunosoral Assay for Rapid Detection of Flumequine in Animal Foods." Food" Anal Method. 2020 Feb;13(2):403-411 3. [IF=3.361] Yuanyuan Zhang et al."Kinetics and mechanisms of flumequine degradation by sulfate radical based AOP in different water samples containing inorganic anions."Rsc Adv. 2022 Mar;12(16):10088-10096 |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
animal-specific antibacterial drug | white powder, odorless, tasteless, insoluble in water and soluble in organic solvents. Flumequine, also known as fluquinic acid and fluhexaquinic acid, is a synthetic second-generation quinolone animal-specific antibacterial drug, and is currently the only broad-spectrum antibacterial veterinary drug that is not shared with humans. It is an alternative product of norfloxacin, has strong bactericidal activity, and has a good effect on animal bacterial diseases. Its main function is to inhibit the deoxynucleic acid (DNA) gyrase of bacteria, so that the synthesis of deoxyribonucleic acid (DNA) protein is disturbed, so that the cell can no longer divide, thereby playing a bactericidal role. Mainly used for livestock and poultry bacterial respiratory diseases, Escherichia coli, pullorum, salmonellosis, typhoid fever, avian cholera, staphylococcal infectious rhinitis, etc. Escherichia coli, Monospora and Arcoccus diseases of aquatic animals, Aeromonas hydrophila have strong inhibition. Flumequine was first successfully developed by Rinker laboratory. It has been widely used in livestock, poultry and aquaculture in the European Union, Japan and other countries since the 2070s. It has a good effect on diseases caused by various gram-negative bacteria infections, especially for diseases of livestock, poultry and aquatic animals caused by Escherichia coli, Mycoplasma and Aeromonas hydrophila. my country gradually developed and marketed in the late 1990s, mainly for the prevention and treatment of bacterial infectious diseases such as salmon, trout, shrimp, eel, pigs and chickens. because the quinolone antibacterial drug flumequine sodium can inhibit bacterial DNA helicase, with wide antibacterial spectrum, high efficiency, low toxicity, strong tissue penetration and no anesthesia effect, it has become one of the most important anti-infective drugs in veterinary clinic and aquaculture, and has been widely used for treatment, prevention and growth promotion. Due to its drug resistance and potential carcinogenicity, the European Union, Japan and China have all set the maximum residue limit in their organizations (both China and the European Union are 100ppb). At present, the detection methods of flumequine mainly include fluorescence spectrophotometry, enzyme-linked method (ELISA) and liquid chromatography. ELISA has become a routine screening method due to its high sensitivity and easy operation. |
biological activity | Flumequine is a synthetic chemotherapy antibiotic that inhibits topoisomerase II with an IC50 of 15 μM. |
Target | Value |
Topo II | 15 μM |
use | is a new broad-spectrum antibacterial synthetic drug with good curative effect on animal bacterial diseases pharmaceutical raw materials |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |