Flumequine

Modify Date: 2024-01-02 16:46:53

Flumequine Structure
Flumequine structure
 Common Name Flumequine
CAS Number 42835-25-6 Molecular Weight 261.248
Density 1.5±0.1 g/cm3 Boiling Point 439.7±45.0 °C at 760 mmHg
Molecular Formula C14H12FNO3 Melting Point 253-255°C
MSDS Chinese USA Flash Point 219.7±28.7 °C

 Use of Flumequine


Flumequine is a quinolone antibiotic, and acts as a topoisomerase II inhibitor, with an IC50 of 15 μM (3.92 μg/mL).

 Names

Name Flumequine
Synonym More Synonyms

 Flumequine Biological Activity

Description Flumequine is a quinolone antibiotic, and acts as a topoisomerase II inhibitor, with an IC50 of 15 μM (3.92 μg/mL).
Related Catalog
Target

Topoisomerase II:15 μM (IC50)
In Vitro Flumequine is a topoisomerase II inhibitor, with an IC50 of 3.92 μg/mL, and less potently inhibits Gyrase, with an IC50 of 1764 μg/mL. Flumequine (0-625 μg/mL) increases migration of nuclear DNA from CHL cells[1]. Flumequine inhibits Spanish field isolates of B. hyodysenteriae with MIC50 and MIC90 of 50 and 100 μg/mL, and MBC50 and MBC90 of 50, 200 μg/mL, respectively[2]. Flumequine suppresses A. salmonicida isolates with MIC ranging from 0.06 to 32 μg/mL[3].
In Vivo Flumequine (0-500 mg/kg, p.o.) causes dose-related DNA damage in the stomach, colon, and urinary bladder of mice, 1 and 3 h but not 24 h after its administration[1].
Kinase Assay Twenty μL of reaction mixture containing 0.4 μg of kinetoplast DNA with 1 U of topoisomerase II and serial dilutions of each antibacterial agent (including Flumequine) are incubated for 5 min at 37°C in buffer containing 20 mM Tris-HCl (pH 7.5), 120 mM KCl, 10 mM MgCl2, 1 mM ATP, 0.5 mM dithiothreitol, and 30 μg/mL of bovine serum albumin. After stopping the reaction by adding sarcosyl with gel-loading buffer, catenated and decatenated kDNAs are separated by agarose gel electrophoresis. The gels are stained with ethidium bromide and photographed using UV light (302 nm) with a Gel Print 200i/VGA, and the brightness of bands is traced with an Image Analyzer. Each band is quantified and the amount of DNA treated with each concentration of quinolone is measured to determine the 50% inhibitory concentration against DNA gyrase and topoisomerase II[1].
Cell Assay The Chinese hamster lung cell line CHL/IU is routinely maintained in monolayer culture in Dulbecco's modified MEM medium supplemented with 10% fetal bovine serum at 37°C under a 5% CO2 atmosphere. Exponentially growing cells are treated with Flumequine dissolved in DMSO for 1 h. The dose range is chosen in order to obtain both damaged and highly damaged cells. Following Flumequine treatment, cells are embedded in GP42 agarose dissolved in saline at 1%. Cell number and cell viability are determined for each dose[1].
Animal Admin Infant and young-adult male ddY mice at 4 and 7 weeks of age, respectively, are used after 1 week of acclimatization. Groups are treated once orally with Flumequine at <500 mg/kg. Adult mice are sacrificed at 3 and 24 h after treatment, and 8 organs, the stomach, colon, liver, kidney, urinary bladder, lung, brain, and bone marrow, are removed. Infant mice are sacrificed 3 and 24 h after treatment, and the livers are excised. In another study, the genotoxicity of Flumequine is studied in the regenerating liver of adult mice. For this purpose, male mice at 8 weeks-of-age are anesthetized with ether and 3 major lobes of the liver, left lateral lobe, left medial lobe, and right lateral lobe, are removed. Four days after the hepatectomy, mice are subjected to oral administration of Flumequine once. They are sacrificed 3 h after FL-treatment and regenerated livers are sampled. Slides for the comet assay are prepared at each set time[1].
References

[1]. Kashida Y, et al. Mechanistic study on flumequine hepatocarcinogenicity focusing on DNA damage in mice. Toxicol Sci. 2002 Oct;69(2):317-21.

[2]. Aller-Morán LM, et al. Evaluation of the in vitro activity of flumequine against field isolates of Brachyspira hyodysenteriae. Res Vet Sci. 2015 Dec;103:51-3.

[3]. Giraud E, et al. Mechanisms of quinolone resistance and clonal relationship among Aeromonas salmonicida strains isolated from reared fish with furunculosis. J Med Microbiol. 2004 Sep;53(Pt 9):895-901.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 439.7±45.0 °C at 760 mmHg
Melting Point 253-255°C
Molecular Formula C14H12FNO3
Molecular Weight 261.248
Flash Point 219.7±28.7 °C
Exact Mass 261.080109
PSA 59.30000
LogP 2.41
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.646
Storage condition 0-6°C
Stability Stable. Incompatible with strong oxidizing agents.

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
Risk Phrases R36/37/38
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
Hazard Class 6.1
HS Code 2933990090

 Synthetic Route

6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline structure

6-Fluoro-2-meth...

CAS#:42835-89-2
Diethyl ethoxymethylenemalonate structure

Diethyl ethoxym...

CAS#:87-13-8

~%

Flumequine Structure

Flumequine

CAS#:42835-25-6
Literature: Minnesota Mining and Manufacturing Company Patent: US4301289 A1, 1981 ; Title/Abstract Full Text Show Details Minnesota Mining and Manufacturing Company Patent: US4301291 A1, 1981 ;
5- [1-(6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolyl)] -methylene-2,2-dimethyl-1,3-dioxan-4,6-dione structure

5- [1-(6-fluoro...

CAS#:123400-74-8

~%

Flumequine Structure

Flumequine

CAS#:42835-25-6
Literature: S P A SOCIETA' PRODOTTI ANTIBIOTICI S.p.a. Patent: EP310849 A1, 1989 ;
9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid ethyl ester structure

9-fluoro-5-meth...

CAS#:42835-47-2

~69%

Flumequine Structure

Flumequine

CAS#:42835-25-6
Literature: Balint, Jozsef; Egri, Gabriella; Fogassy, Elemer; Boecskei, Zsolt; Simon, Kalman; Gajary, Antal; Friesz, Antal Tetrahedron Asymmetry, 1999 , vol. 10, # 6 p. 1079 - 1087
5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione structure

5-(Methoxymethy...

CAS#:15568-85-1
6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline structure

6-Fluoro-2-meth...

CAS#:42835-89-2

~%

5- [1-(6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolyl)] -methylene-2,2-dimethyl-1,3-dioxan-4,6-dione structure

5- [1-(6-fluoro...

CAS#:123400-74-8
Flumequine Structure

Flumequine

CAS#:42835-25-6
Literature: S P A SOCIETA' PRODOTTI ANTIBIOTICI S.p.a. Patent: EP310849 A1, 1989 ;
6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline structure

6-Fluoro-2-meth...

CAS#:42835-89-2

~%

Flumequine Structure

Flumequine

CAS#:42835-25-6
Literature: Balint, Jozsef; Egri, Gabriella; Fogassy, Elemer; Boecskei, Zsolt; Simon, Kalman; Gajary, Antal; Friesz, Antal Tetrahedron Asymmetry, 1999 , vol. 10, # 6 p. 1079 - 1087
N/A structure

N/A

CAS#:105450-09-7

~%

Flumequine Structure

Flumequine

CAS#:42835-25-6
Literature: Balint, Jozsef; Egri, Gabriella; Fogassy, Elemer; Boecskei, Zsolt; Simon, Kalman; Gajary, Antal; Friesz, Antal Tetrahedron Asymmetry, 1999 , vol. 10, # 6 p. 1079 - 1087

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Articles9

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Growing interest in the use of both the logarithm of the partition coefficient of the neutral species in the alkane/water system (log P(N)(alk)) and the difference between log P(N)(oct) (the logarithm...
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gyrA and parC Mutations and associated quinolone resistance in Vibrio anguillarum serotype O2b strains isolated from farmed Atlantic cod (Gadus morhua) in Norway.

Antimicrob. Agents Chemother. 51 , 2597-9, (2007)

MIC testing of Vibrio anguillarum isolates recovered from diseased farmed Atlantic cod revealed oxolinic acid MICs of < or =0.001, 0.06, and 16 microg ml(-1). Single gyrA Ser-Ile substitutions were id...

 Synonyms

Apurone
UNII:UVG8VSP2SJ
Quinolone
9-Fluoro-5-methyl-1-oxo-1,5,6,7-tetrahydropyrido[3,2,1-ij]quinoline-2-carboxylic acid
FLUMEQUIN
Flumeguine
EINECS 255-962-6
1H,5H-Benzo[ij]quinolizine-2-carboxylic acid, 9-fluoro-6,7-dihydro-5-methyl-1-oxo-
9-Fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid
MFCD00079298
Imequyl
9-Fluoro-1,5,6,7-tetrahydro-5-methyl-1-oxopyrido[3,2,1-ij]quinoline-2-carboxylic Acid
Flumural
Flumequine
Aoyribe
Fantacin
R 802
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Related Compounds: More...
(S)-FluMequine
202349-45-9
(R)-flumequine
215178-95-3
Flumequine-13C3
1185049-09-5
Flumequine sodium
42835-68-7
Chemsrc provides Flumequine(CAS#:42835-25-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Flumequine are included as well.>> amp version: Flumequine

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