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Merck
CN

F6807

Fleroxacin

Synonym(s):

RO 23-6240, 6,8-Difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methylpiperazino)-4-oxo-3-quinolinecarboxylic acid, 6,8-Difluoro-1-(2-fluoroethyl)1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid, AM-833, Megalocin, Megalone

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About This Item

Empirical Formula (Hill Notation):
C17H18F3N3O3
CAS Number:
79660-72-3
Molecular Weight:
369.34
NACRES:
NA.85
PubChem Substance ID:
329799758
UNSPSC Code:
51102829
MDL number:
MFCD00864880

Key Documents

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InChI

1S/C17H18F3N3O3/c1-21-4-6-22(7-5-21)15-12(19)8-10-14(13(15)20)23(3-2-18)9-11(16(10)24)17(25)26/h8-9H,2-7H2,1H3,(H,25,26)

SMILES string

CN1CCN(CC1)c2c(F)cc3C(=O)C(=CN(CCF)c3c2F)C(O)=O

InChI key

XBJBPGROQZJDOJ-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

0.1 M NaOH: 10 mg/mL

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, mycobacteria, mycoplasma

mode of action

DNA synthesis | interferes, enzyme | inhibits

storage temp.

−20°C

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Application

Fleroxacin is a broad-spectrum antimicrobial fluoroquinolone. It is used in pharmacokinetic studies and is used to study the treatment of intra-abdominal abscesses and travellers′ diarrhea.

Biochem/physiol Actions

Fleroxacin is a synthetic trifluorinated quinolone with antimicrobial activity against a variety of pathogens, including mycobacteria, mycoplasmas, chlamydiae, and legionellae. It strongly inhibits the DNA-supercoiling activity of DNA gyrase and DNA topoisomerase 2, which results in cell death.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL5091
080M1481

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A Pefanis et al.
Antimicrobial agents and chemotherapy, 38(2), 252-255 (1994-02-01)
To assess the potential efficacy of fleroxacin in combination with clindamycin or metronidazole in mixed aerobic and anaerobic infections, we used a rat model of intra-abdominal abscesses in which the inoculum consisted of pooled rat feces mixed with BaSO4. Two
R Steffen et al.
The Journal of antimicrobial chemotherapy, 31(5), 767-776 (1993-05-01)
A double-blind, randomized, placebo-controlled trial was conducted to evaluate the efficacy and safety of fleroxacin for one or two days as treatment for patients with travellers' diarrhoea. A total of 195 patients who were suffering with acute diarrhoea of less
J C Akaniro et al.
Antimicrobial agents and chemotherapy, 34(10), 1880-1884 (1990-10-01)
We evaluated fleroxacin, a newer fluoroquinolone, against isolates from sputum from patients with cystic fibrosis. These isolates included rough and mucoid Pseudomonas aeruginosa, Pseudomonas cepacia, Staphylococcus aureus, Haemophilus influenzae, and Escherichia coli. Selected isolates were tested by the broth microdilution
Xiaozhang Zhu et al.
Journal of the American Chemical Society, 133(41), 16342-16345 (2011-09-22)
A heptacyclic carbocycle possessing three p-quinodimethane units conjugated in one plane has been synthesized and shown to exhibit distinct biradical characteristics. The molecule has a HOMO/LUMO band gap of ca. 1 eV and a S(0)-T(1) energy gap of 2.12 kcal/mol
Benjamin Waibel et al.
Journal of pharmaceutical and biomedical analysis, 43(5), 1595-1601 (2007-01-27)
In order to investigate and characterize interaction processes between the fluoroquinolone fleroxacin and bacterial cells we used non-selective (all resonances are excited), selective (observed resonance is excited) spin-lattice relaxation rates and spin-spin relaxation measurements. The signals of three hydrogens at
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