Grepafloxacin

Structural formula
Structural formula without stereochemistry
General
Non-proprietary name	Grepafloxacin
other names	( RS ) -1-Cyclopropyl-6-fluoro-5-methyl-7- (3-methylpiperazin-1-yl) -4-oxo-1,4-dihydroquinoline-3-carboxylic acid ( IUPAC ) (±) -1-Cyclopropyl-6-fluoro-5-methyl-7- (3-methylpiperazin-1-yl) -4-oxo-1,4-dihydroquinoline-3-carboxylic acid rac -1-Cyclopropyl-6-fluoro-5-methyl-7- (3-methylpiperazin-1-yl) -4-oxo-1,4-dihydroquinoline-3-carboxylic acid Grepafloxacinum ( Latin )
Molecular formula	C 19 H 22 FN 3 O 3
External identifiers / databases
CAS number 119914-60-2 EC number 631-454-3 ECHA InfoCard 100.159.692 PubChem 72474 ChemSpider 65391 DrugBank DB00365 Wikidata Q414846
Drug information
ATC code	J01 MA11
Drug class	Antibiotics
Mechanism of action	Gyrase inhibitors
properties
Molar mass	359.39 g · mol -1
Physical state	firmly
Melting point	206-208 ° 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 danger H and P phrases H: 301 P: ?
Toxicological data	3029 mg kg −1 ( LD 50 ,  rat ,  oral , monohydrochloride)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Grepafloxacin is a broad spectrum antibiotic belonging to the group of fluoroquinolones . Antibiotics from the group of fluoroquinolones are a subgroup of the quinolones , they act as gyrase inhibitors against gram-positive bacteria ( hemophilus , legionella , mycoplasma , chlamydia, etc.), especially in respiratory infections.

Grepafloxacin was patented in 1989 by the pharmaceutical company Warner-Lambert (now Pfizer ). After some patients as a side effect of the long QT syndrome , an arrhythmia occurred with seven deaths associated with taking the drug, it was taken by the manufacturer end of October 1999 worldwide from the market.

Stereochemistry

Grepafloxacin contains a stereocenter and consists of two enantiomers. This is a racemate , i.e. a 1: 1 mixture of ( R ) - and ( S ) -form:

Grepafloxacin enantiomers
CAS number: 146761-68-4	CAS number: 146761-69-5

literature

• W. Forth, D. Henschler, W. Rummel: General and special pharmacology and toxicology . 9th edition. URBAN & FISCHER, Munich 2005, ISBN 3-437-42521-8 .

Individual evidence

1. ↑ ^{a b} Entry on grepafloxacin. In: Römpp Online . Georg Thieme Verlag, accessed on May 30, 2014.
2. ↑ There is not yet a harmonized classification for this substance . A labeling of grepafloxacin in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was accessed on May 26, 2020, is reproduced from a self-classification by the distributor .
3. ↑ FURTHER CRASH CANDIDATES? CARDIOTOXICITY OF GYRASIS inhibitors . Remedy telegram . S. 120 November 1999. Retrieved June 4, 2009.

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !