Cinoxacin

Structural formula
General
Surname	Cinoxacin
other names	1-ethyl-1,4-dihydro-4-oxo-1,3-dioxolo [4.5 g ] cinnoline-3-carboxylic acid; 1-Ethyl-6-7-methylenedioxy-4 (1 H ) -oxocinnoline-3-carboxylic acid;
Molecular formula	C 12 H 10 N 2 O 5
External identifiers / databases
EC number	249-133-8
ECHA InfoCard	100.044.652
PubChem	2762
ChemSpider	2660
DrugBank	DB00827
Wikidata	Q1639588
Drug information
ATC code	G04 AB05
Drug class	Quinolone antibiotics
Mechanism of action	Gyrase inhibitors
properties
Molar mass	262.22 g mol −1
Physical state	firmly
Melting point	261–262 ° C (decomposition)
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	4160 mg kg −1 ( LD 50 , rat , oral ) ; 900 mg kg −1 ( LD 50 , rat , iv ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cinoxacin is a drug from the group of quinolone antibiotics . It was first patented by Lilly in 1970 and used to treat urinary tract infections. However, the substance has not been approved in Germany for a long time.

properties

Cinoxacin is in light brown crystal form. It is soluble in most polar organic solvents. It has a higher cure rate than nalidixic acid and only needs to be taken twice a day. Due to the serious side effects caused by taking cinoxacin, the drug has been withdrawn from the market in Europe by the Federal Institute for Drugs and Medical Devices ( BfArM ) since April 2019 .

synthesis

The synthesis of cinoxacin is summarized in the literature.

Individual evidence

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

↑ ^a ^b ^c Entry on cinoxacin. In: Römpp Online . Georg Thieme Verlag, accessed on April 16, 2020.

↑ ^a ^b M. Sabbour, M. Bokl, L. Osman: Experiences on the efficacy and safety of nalidixic acid, oxolinic acid, cinoxacin and norfloxacin in the treatment of urinary tract infections (UTI). In: Infection , 1984, Vol. 12, No. 6, pp. 377-380, doi: 10.1007 / BF01645218 .

↑ ^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 .

^ 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. 386.

^ A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances Online. Thieme, Stuttgart, accessed on April 15, 2020.

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

[Römpp-2] Entry on cinoxacin. In: Römpp Online . Georg Thieme Verlag, accessed on April 16, 2020.

[Sabbour-3] M. Sabbour, M. Bokl, L. Osman: Experiences on the efficacy and safety of nalidixic acid, oxolinic acid, cinoxacin and norfloxacin in the treatment of urinary tract infections (UTI). In: Infection , 1984, Vol. 12, No. 6, pp. 377-380, doi: 10.1007 / BF01645218 .

[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 .

[MERCK_Index-5] 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. 386.

[Pharmaceutical_Substances-6] A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances Online. Thieme, Stuttgart, accessed on April 15, 2020.