Fleroxacin

Structural formula
General
Surname	Fleroxacin
other names	6,8-Difluoro-1- (2-fluoroethyl) -1,4-dihydro-7- (4-methyl-1-piperazinyl) -4-oxo-quinoline-3-carboxylic acid;
Molecular formula	C 17 H 18 F 3 N 3 O 3
External identifiers / databases
EC number	677-525-2
ECHA InfoCard	100.202.650
PubChem	3357
ChemSpider	3240
DrugBank	DB04576
Wikidata	Q3746573
Drug information
ATC code	J01 MA08
Drug class	Quinolone antibiotics
Mechanism of action	Gyrase inhibitors
properties
Molar mass	369.34 g mol −1
Physical state	firmly
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	21.7 mg kg −1 ( LD 50 , mouse , iv ) ; > 4 g kg −1 ( LD 50 , mouse , oral ) ; > 4 g kg −1 ( LD 50 , rat , oral ) ; 20.4 g kg −1 ( LD 50 , rat , iv ) ; > 1 g kg −1 ( LD 50 , dog , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fleroxacin is a drug from the group of quinolone antibiotics , more precisely the fluoroquinolone antibiotics . It was the first time in 1981 by Kyorin patented and is in the form of mono hydrochloride used. In Germany, the drug was on the market from 1995 to 2003 under the name Quinodis .

properties

The antimicrobial spectrum includes a number of gram-negative germs, including Enterobacteriaceae such as Klebsiella , E. coli , Salmonella , Shigella and Yersinia as well as Haemophilus and Neisseria , and Fleroxacin is also very effective against many staphylococci . It is less effective against Pseudomonas , but largely ineffective against streptococci and enterococci .

use

Fleroxacin is one of the fluoroquinolones with a wide range of indications. It can be administered either orally or parenterally, with a single dose usually being sufficient. It can be used to treat infections of the lower urinary tract, respiratory tract, and skin, among other things. Compared to other antibiotics, the use of Fleroxacin led to an increased incidence of undesirable effects after the market launch , which led to the drug being withdrawn from the market.

Pharmacokinetics

After oral administration, the substance is rapidly and almost completely absorbed ; maximum plasma levels occur after 1 to 2 hours. The half-life is 10 to 12 hours, which is why a single dose per day is sufficient. Most of the excretion is renal , i.e. H. through the kidneys.

Individual evidence

↑ ^a ^b Fleroxacin data sheet from Sigma-Aldrich , accessed on April 14, 2020 ( PDF ).

↑ ^a ^b ^c ^d ^e ^f Entry on Fleroxacin. In: Römpp Online . Georg Thieme Verlag, accessed on April 15, 2020.

^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006, ISBN 978-0-911910-00-1 , pp. 700.

↑ U. Schwabe, D. Paffrath (Ed.): Drug Ordinance Report 2003 . Springer-Verlag, Berlin / Heidelberg 2004, p. 72 .

^ Medicines update. German STI Society (DSTIG), accessed on April 22, 2020 .

↑ ^a ^b K. Tobler: Fleroxacin . In: pharma criticism . tape 15 , no. 4 , 2004 ( infomed.ch [PDF]).

↑ Katrin Farker, Kurt G. Naber, Reinhard Fünfstück: Fluoroquinolones: Use in infections of the kidney and the urogenital tract . In: Medical Clinic , 2001, Vol. 96, No. 7, pp. 383-390, doi: 10.1007 / s00063-001-1063-2 .

↑ Winfried Kern: Quinolone Toxicity - New and Newly Reviewed . In: Deutsche Medizinische Wochenschrift , 2019, Volume 144, No. 24, pp. 1697–1702, doi: 10.1055 / a-0899-2883 .

[Sigma-1] Fleroxacin data sheet from Sigma-Aldrich , accessed on April 14, 2020 ( PDF ).

[Römpp-2] ↑ ^a ^b ^c ^d ^e ^f Entry on Fleroxacin. In: Römpp Online . Georg Thieme Verlag, accessed on April 15, 2020.

[MERCK_Index-3] The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006, ISBN 978-0-911910-00-1 , pp. 700.

[4] U. Schwabe, D. Paffrath (Ed.): Drug Ordinance Report 2003 . Springer-Verlag, Berlin / Heidelberg 2004, p. 72 .

[5] Medicines update. German STI Society (DSTIG), accessed on April 22, 2020 .

[pk1993-6] K. Tobler: Fleroxacin . In: pharma criticism . tape 15 , no. 4 , 2004 ( infomed.ch [PDF]).

[7] Katrin Farker, Kurt G. Naber, Reinhard Fünfstück: Fluoroquinolones: Use in infections of the kidney and the urogenital tract . In: Medical Clinic , 2001, Vol. 96, No. 7, pp. 383-390, doi: 10.1007 / s00063-001-1063-2 .

[Kern-8] Winfried Kern: Quinolone Toxicity - New and Newly Reviewed . In: Deutsche Medizinische Wochenschrift , 2019, Volume 144, No. 24, pp. 1697–1702, doi: 10.1055 / a-0899-2883 .