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F7016

Sigma-Aldrich

Flumequine

≥97.0% (HPLC)

Synonym(s):

9-Fluoro-5-methyl-1-oxo-1,5,6,7-tetrahydropyrido[3,2,1-ij]quinoline-2-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C14H12FNO3
CAS Number:
42835-25-6
Molecular Weight:
261.25
Beilstein/REAXYS Number:
490724
EC Number:
255-962-6
MDL number:
MFCD00079298
UNSPSC Code:
51102829
PubChem Substance ID:
24894926
NACRES:
NA.85

assay

≥97.0% (HPLC)

form

powder

color

white to off-white

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

mode of action

DNA synthesis | interferes
enzyme | inhibits

SMILES string

CC1CCc2cc(F)cc3C(=O)C(=CN1c23)C(O)=O

InChI

1S/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)

InChI key

DPSPPJIUMHPXMA-UHFFFAOYSA-N

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General description

Chemical structure: fluoroquinolone

Biochem/physiol Actions

Flumequine inhibits topoisomerases, which are needed for the transcription and replication of bacterial DNA. The inhibition of the topoisomerases results in strand breakage of the bacterial chromosome, supercoiling, and resealing. Therefore, DNA replication and transcription is inhibited .

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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I Guillemin et al.
Microbiology (Reading, England), 145 ( Pt 9), 2527-2532 (1999-10-12)
The DNA gyrases from Mycobacterium avium, Mycobacterium smegmatis and Mycobacterium fortuitum bv. peregrinum, which are species naturally resistant, moderately susceptible and susceptible to fluoroquinolones, respectively, were purified by affinity chromatography on novobiocin-Sepharose columns. The DNA gyrase inhibiting activities (IC50 values)
Etienne Giraud et al.
Journal of medical microbiology, 53(Pt 9), 895-901 (2004-08-18)
The mechanisms of resistance to quinolone and epidemiological relationships among A. salmonicida strains isolated from diseased fish in French marine farms from 1998 to 2000 were investigated. The quinolone resistance-determining regions of the gyrA and parC genes of 12 clinical
Yoko Kashida et al.
Toxicological sciences : an official journal of the Society of Toxicology, 69(2), 317-321 (2002-10-16)
In order to elucidate the tumor-initiating potential of flumequine (FL) in the liver, male C3H mice were given dietary administration of 4000 ppm FL throughout the study or for 2 weeks at the initiation stage, and then received 2 intraperitoneal
E Giraud et al.
Antimicrobial agents and chemotherapy, 43(9), 2131-2137 (1999-09-03)
The occurrence of mutations in the genes coding for gyrase (gyrA and gyrB) and topoisomerase IV (parE and parC) of Salmonella typhimurium experimental mutants selected in vitro and in vivo and of 138 nalidixic acid-resistant Salmonella field isolates was investigated.
C Ferraresi et al.
Poultry science, 92(12), 3158-3165 (2013-11-16)
Flumequine (FLU) is used in the treatment of systemic bacterial infections in poultry, including colibacillosis, which is a common disease in turkeys. The pharmacokinetic (PK) behavior of FLU administered to 32 healthy turkeys as an oral bolus via gavage or
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