Flumequin

Structural formula
	Racemate - the stereocenter is marked with an asterisk *
General
Surname	Flumequin
other names	( RS ) -9-Fluoro-5-methyl-1-oxo-6,7-dihydro-1 H , 5 H -benzo [ ij ] quinolizine-2-carboxylic acid ( IUPAC ) ; (±) -9-fluoro-5-metyl-1-oxo-6,7-dihydro-1 H , 5 H -benzo [ ij ] quinolizine-2-carboxylic acid; Flumechine;
Molecular formula	C 14 H 12 FNO 3
External identifiers / databases
EC number	255-962-6
ECHA InfoCard	100.050.857
PubChem	3374
ChemSpider	3257
DrugBank	DB08972
Wikidata	Q3074500
Drug information
ATC code	G04 AB06
Drug class	Quinolone antibiotics
Mechanism of action	Gyrase inhibitors
properties
Molar mass	261.25 g mol −1
Physical state	firmly
Melting point	253-255 ° C
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	3915 mg kg −1 ( LD 50 , mouse , iv )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Flumequin is a drug belonging to the group of quinolone antibiotics , more precisely the fluoroquinolone antibiotics . It was first patented in 1973.

It is used in veterinary medicine to treat bacterial infections. The substance was never approved for the market in Germany. In April 2019, Flumequin was withdrawn from the market for human use in Europe after a risk assessment process found that the severity of the side effects did not justify its use.

properties

Flumequin is a white to almost white microcrystalline powder. It is practically insoluble in water, sparingly soluble in dichloromethane and very sparingly soluble in methanol . In dilute alkali - solution , the substance is readily soluble.

chemistry

synthesis

The synthesis of flumequin is summarized in the literature.

Stereoisomerism

The compound is chiral and is used as a racemate ; i.e., used as a 1: 1 mixture of the two enantiomers . The table shows the structural formulas of the two enantiomers:

Flumequin's enantiomers
( S ) -enantiomer	( R ) -enantiomer

Web links

Entry on Flumequin at Vetpharm, accessed April 18, 2020.

Individual evidence

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

^ ^A ^b 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 , P. 707.

↑ ^a ^b Entry on fluoroquinolones. In: Römpp Online . Georg Thieme Verlag, accessed on April 13, 2020.

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

↑ Risk assessment procedure EMEA / H / A-31/1452: Quinolone- and fluoroquinolone-containing medicinal products , EMA , March 2019.

↑ ^a ^b European Pharmacopoeia , Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, ISBN 978-3-7692-3962-1 , pp. 2592-2593.

^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , Thieme-Verlag Stuttgart, 5th edition (2009), ISBN 978-3-13-558405-8 , p. 411; also online with biannual additions and updates.

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

[MERCK_Index-2] A ^b 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 , P. 707.

[Römpp-3] Entry on fluoroquinolones. In: Römpp Online . Georg Thieme Verlag, accessed on April 13, 2020.

[Kern-4] Winfried Kern: Quinolone Toxicity - New and Newly Evaluated . In: Deutsche Medizinische Wochenschrift, 2019, Volume 144, No. 24, pp. 1697–1702, doi: 10.1055 / a-0899-2883 .

[5] Risk assessment procedure EMEA / H / A-31/1452: Quinolone- and fluoroquinolone-containing medicinal products , EMA , March 2019.

[Europäisches_Arzneibuch-6] European Pharmacopoeia , Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, ISBN 978-3-7692-3962-1 , pp. 2592-2593.

[Kleemann-7] Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , Thieme-Verlag Stuttgart, 5th edition (2009), ISBN 978-3-13-558405-8 , p. 411; also online with biannual additions and updates.