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Flumequine

Product Name
Flumequine
CAS No.
42835-25-6
Chemical Name
Flumequine
Synonyms
Quinolone;FLUMEQUIN;Fluoromethyl;R 802;Apurone;Aoyribe;Imequyl;Fantacin;Flumural;Flumigal
CBNumber
CB1264632
Molecular Formula
C14H12FNO3
Formula Weight
261.25
MOL File
42835-25-6.mol
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Flumequine Property

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. 
Sealed in dry,Store in freezer, under -20°C
solubility 
1 M NH4OH: soluble50mg/mL
pka
pKa 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 Reference
42835-25-6(CAS DataBase Reference)
EPA Substance Registry System
1H,5H-Benzo[ij]quinolizine-2-carboxylic acid, 9-fluoro-6,7-dihydro-5-methyl-1-oxo- (42835-25-6)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
22-24/25-36/37/39-27-26
WGK Germany 
3
10
HS Code 
29339900
Hazardous Substances Data
42835-25-6(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
45735
Product name
Flumequine
Purity
VETRANAL
Packaging
250mg
Price
$70
Updated
2024/03/01
Sigma-Aldrich
Product number
F7016
Product name
Flumequine
Packaging
1g
Price
$54.6
Updated
2023/06/20
TCI Chemical
Product number
F0832
Product name
Flumequine
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$91
Updated
2021/12/16
TCI Chemical
Product number
F0832
Product name
Flumequine
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$246
Updated
2023/01/07
Alfa Aesar
Product number
J66332
Product name
Flumequine, 98%
Packaging
1g
Price
$48.3
Updated
2024/03/01
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Flumequine Chemical Properties,Usage,Production

Description

Flumequine is a synthetic antibiotic belonging to the second-generation quinolone group and is mainly active against Gram negative bacteria. 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 used in bovine, ovine, chicken, rabbits, goats, horses and salmonidae, however the establishment of MRLs was only requested for non-lactating cattle, pigs, sheep, chicken and salmonidae.

Chemical Properties

White Crystalline Solid

Originator

Apurone,Riker,France,1977

Uses

Flumequine is a fluoroquinolone compound with antimicrobial activity against Gram-negative organisms. It is used in the treatment of enteric infections in food animals and in the treatment of bacterial infections in farmed fish. Flumequine is replacing oxolinic acid in aquaculture because of its more appropriate pharmacokinetic profile and lower effective doses (Treves-Brown 2000). Flumequine also has limited use in humans for the treatment of urinary tract infections.

Definition

ChEBI: Flumequine is a member of the class of pyridoquinolines that is 1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline carrying additional carboxy, methyl and fluoro substituents at positions 2, 5 and 9 respectively. It is a pyridoquinoline, a 3-oxo monocarboxylic acid, an organofluorine compound and a quinolone antibiotic.

Preparation

Synthesis: Condensation of 5-fluoro-2-methyltetrahydroquinoline with diethyl ethoxy-methylenemalonate followed by thermal cycli- zation gives ethyl 6,7-dihydro-9-fluoro-5-meth-yl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-car-boxylate,which is saponified with sodium hydroxide to give flumequine.

Manufacturing Process

6-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 Function

Antibacterial

Pharmaceutical Applications

A 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 Preparation Products And Raw materials

Raw materials

Preparation Products

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Flumequine Suppliers

Wuhan Hongde Yuexin Pharmatech Co.,Ltd
Tel
027-83850116 18164090116
Fax
027-83850116
Email
whhdyxchem123@sina.com
Country
China
ProdList
4263
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44689
Advantage
61
Beijing Ouhe Technology Co., Ltd
Tel
010-82967028 13552068683
Fax
+86-10-82967029
Email
2355560935@qq.com
Country
China
ProdList
12390
Advantage
60
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
chenyj@titansci.com
Country
China
ProdList
14103
Advantage
59
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
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View Lastest Price from Flumequine manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Flumequine 42835-25-6
Price
US $100.00/kg
Min. Order
1kg
Purity
99
Supply Ability
5000
Release date
2024-04-24
Hebei Lingding Biotechnology Co., Ltd.
Product
Flumequine 42835-25-6
Price
US $50.00/KG
Min. Order
0.5KG
Purity
99%
Supply Ability
1 T
Release date
2025-01-21
Hebei Lingding Biotechnology Co., Ltd.
Product
Flumequine 42835-25-6
Price
US $50.00/KG
Min. Order
0.5KG
Purity
99%
Supply Ability
1 T
Release date
2025-01-21

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  • Antibiotics
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