Nadifloxacin

Structural formula
	( R ) -Nadifloxacin (top) and ( S ) -Nadifloxacin (bottom)
General
Non-proprietary name	Nadifloxacin
other names	(±) -9-Fluoro-8- (4-hydroxypiperidino) -5-methyl-1-oxo-6,7-dihydro-1 H , 5 H -benzo [ ij ] quinolizine-2-carboxylic acid ( IUPAC ) ; ( RS ) -9-fluoro-8- (4-hydroxypiperidino) -5-methyl-1-oxo-6,7-dihydro-1 H , 5 H -benzo [ ij ] quinolizine-2-carboxylic acid; rac -9-fluoro-8- (4-hydroxypiperidino) -5-methyl-1-oxo-6,7-dihydro-1 H , 5 H -benzo [ ij ] quinolizine-2-carboxylic acid; Nadifloxacinum ( Latin ) ;
Molecular formula	C 19 H 21 FN 2 O 4
Brief description	colorless prisms (made of ethanol + water)
External identifiers / databases
EC number	638-863-6
ECHA InfoCard	100.166.530
PubChem	4410
ChemSpider	4257
DrugBank	DB12447
Wikidata	Q426605
Drug information
ATC code	D10 AF
Drug class	Fluoroquinolone - Antibiotics
Mechanism of action	Gyrase inhibitors
properties
Molar mass	360.38 g · mol -1
Physical state	firmly
Melting point	245–247 ° 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 Caution
H and P phrases	H: 362-373
	P: ?
Toxicological data	376.5 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 .

Nadifloxacin is an antibiotic substance from the group of fluoroquinolones ( gyrase inhibitors ).

Chemical properties

Nadifloxacin has a benzo [ ij ] quinolizine structure with a fluorine atom at position 9 and a 4-hydroxypiperidine residue at position 8. The substance has a chiral center and is present as a racemate .

Mechanism of action

Nadifloxacin causes DNA gyrase to inhibit the folding of DNA . The gyrase is an enzyme and enables the orderly accommodation of the entire DNA strand of a bacterium in a bacterial cell. The gyrase takes care of the twisting of the DNA strand by opening and closing the strand so that the whole strand does not have to rotate. In the event of a gyrase obstruction, the strand opened for twisting cannot close again. The replication of the cell is disturbed. The bacterium dies.

Nadifloxacin has been shown to be effective against a wide range of gram-positive and gram-negative bacteria including anaerobes ( Propionibacterium acnes) in various in vitro and in vivo studies . The exact extent of absorption of nadifloxacin cream after topical application to acne- affected skin varies. A single dose of 10 g of a 1% nadifloxacin cream applied to the backs of healthy volunteers resulted in a mean maximum plasma concentration of 0.54 ng / ml. The mean plasma half-life of nadifloxacin was 12.7 hours. After repeated application of 5 g of a 1% nadifloxacin cream twice daily to healthy volunteers over a period of 7 days, the steady-state plasma concentration was reached on the 5th day. The maximum plasma concentration of 1.34 ng / ml was reached 8 hours after the last application. Over a period of 192 hours, an average of 0.013% of the administered dose of nadifloxacin was recovered in the urine .

After absorption, both unchanged nadifloxacin and metabolites were found in the urine and faeces . The degree of absorption depends on the condition of the stratum corneum .

application

In medicine, nadifloxacin is used for acne vulgaris , folliculitis , sycosis vulgaris , atopic dermatitis and impetigo . Nadifloxacin is only used topically .

Side effects

Known side effects of nadifloxacin are itching, papules , contact dermatitis , skin irritation, sensation of warmth, flushing (attacks of reddening of the skin with sensation of heat), erythema , urticaria , hypopigmentation of the skin.

Resistances

In various studies, nadifloxacin showed only a low rate of spontaneous resistance formation compared with older topical antibiotics.

Trade names

Nadixa (D, AT), Acuatim (J)

literature

Hermann J. Roth: Medicinal Chemistry: Targets and Drugs; 157 tables . German Apotheker-Verlag, Stuttgart 2005, ISBN 3-7692-3483-9

Individual evidence

^ ^A ^b ^c 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 .
↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A label of [No public or meaningful name is available] in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on July 8, 2020, is reproduced from a self-classification by the distributor .
↑ Alba V, Urban E, Angeles Dominguez M, et al. : In vitro activity of nadifloxacin against several Gram-positive bacteria and analysis of the possible evolution of resistance after 2 years of use in Germany . In: Int. J. Antimicrob. Agents . 33, No. 3, March 2009, pp. 272-275. PMID 19095414 .
↑ Murata K, Tokura Y: Anti-microbial therapies for acne vulgaris: anti-inflammatory actions of anti-microbial drugs and their effectiveness . In: Journal of UOEH . 29, No. 1, March 2007, pp. 63-71. PMID 17380730 .
↑ Nakaminami H, Noguchi N, Ikeda M, et al. : Molecular epidemiology and antimicrobial susceptibilities of 273 exfoliative toxin-encoding-gene-positive Staphylococcus aureus isolates from patients with impetigo in Japan . In: Journal of Medical Microbiology . 57, No. Pt 10, October 2008, pp. 1251-1258. doi : 10.1099 / jmm.0.2008 / 002824-0 . PMID 18809554 .

[MERCK_Index-1] A ^b ^c 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 .

[2] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A label of [No public or meaningful name is available] in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on July 8, 2020, is reproduced from a self-classification by the distributor .

[pmid-3] Alba V, Urban E, Angeles Dominguez M, et al. : In vitro activity of nadifloxacin against several Gram-positive bacteria and analysis of the possible evolution of resistance after 2 years of use in Germany . In: Int. J. Antimicrob. Agents . 33, No. 3, March 2009, pp. 272-275. PMID 19095414 .

[pmid17380730-4] Murata K, Tokura Y: Anti-microbial therapies for acne vulgaris: anti-inflammatory actions of anti-microbial drugs and their effectiveness . In: Journal of UOEH . 29, No. 1, March 2007, pp. 63-71. PMID 17380730 .

[pmid18809554-5] Nakaminami H, Noguchi N, Ikeda M, et al. : Molecular epidemiology and antimicrobial susceptibilities of 273 exfoliative toxin-encoding-gene-positive Staphylococcus aureus isolates from patients with impetigo in Japan . In: Journal of Medical Microbiology . 57, No. Pt 10, October 2008, pp. 1251-1258. doi : 10.1099 / jmm.0.2008 / 002824-0 . PMID 18809554 .