Norfloxacin

Structural formula
General
Non-proprietary name	Norfloxacin
other names	1-Ethyl-6-fluoro-4-oxo-7- (piperazin-1-yl) -1,4-dihydroquinoline-3-carboxylic acid ( IUPAC ); Norfloxacinum ( Latin );
Molecular formula	C 16 H 18 FN 3 O 3
Brief description	white to pale yellow, hygroscopic , light-sensitive, crystalline powder
External identifiers / databases
EC number	274-614-4
ECHA InfoCard	100,067,810
PubChem	4539
ChemSpider	4380
DrugBank	DB01059
Wikidata	Q417897
Drug information
ATC code	J01 MA06 ; S01 AE02 ;
Drug class	Fluoroquinolone - Antibiotics
Mechanism of action	Gyrase inhibitors
properties
Molar mass	319.33 g · mol -1
Physical state	firmly
Melting point	227-228 ° C
pK s value	6.34; 9.75
solubility	very sparingly soluble in water, sparingly soluble in acetone and ethanol ; freely soluble in glacial acetic acid ;
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	245 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 .

Norfloxacin is a synthetic broad spectrum antibiotic from the group of gyrase inhibitors and is orally effective. It belongs to the fluoroquinolone class of substances .

properties

The colorless to pale yellow, crystalline powder has unlimited solubility in glacial acetic acid , very sparingly soluble in water , sparingly soluble in ethanol 96% and acetone .

Norfloxacin shows high in-vitro activity against a wide range of gram-positive and gram-negative aerobic bacteria .

pharmacology

The bioavailability after oral administration in the human body is between 50 and 70%. With a blood plasma half-life of 3–6 hours, 26–40% of the active substance is excreted unchanged via the kidneys .

application areas

Norfloxacin is mainly prescribed to treat urinary tract infections and gonorrhea . The most important side effects are typical for the fluoroquinolone class of substances . These include nausea, loss of appetite, vomiting, dizziness, and neuropsychiatric reactions. Very rarely, all gyrase inhibitors - even after short-term use - can rupture large tendons, e.g. B. come to the Achilles tendon rupture . Note the interaction with caffeine described for ciprofloxacin . It is definitely forbidden ( contraindication ) to administer norfloxacin during pregnancy and breastfeeding. Furthermore, norfloxacin must not be administered until the end of the growth period (exception: cystic fibrosis ).

Based on the recommendation of the European Medicines Agency , the Federal Institute for Drugs and Medical Devices changed the indications in February 2009 due to an unfavorable risk-benefit assessment and insufficiently proven efficacy so that drugs containing norfloxacin are no longer approved for the treatment of complicated pyelonephritis are.

Trade names

Bactracid (D), Barazan (D), Chibroxin (D), Firin (D), Floxacin (A), Norfluxx (D), Noroxin (CH), Norsol (CH), Zoroxin (A), various generics (D, A, CH)

Individual evidence

↑ ^a ^b ^c ^d European Pharmacopoeia Commission (Ed.): European Pharmacopoeia, 9th edition, 3rd supplement. 2018.
↑ ^a ^b Entry on norfloxacin in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on May 21, 2019.
^ Entry on norfloxacin. In: Römpp Online . Georg Thieme Verlag, accessed on July 19, 2019.
^ ^A ^b D. B. Troy: Remington: The Science and Practice of Pharmacy , p. 1658, 21st edition, Lippincott Raven, 2005, ISBN 0-7817-4673-6 .
↑ ^a ^b Data sheet norfloxacin from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).
↑ Schubert-Zsilavecz, Manfred., Roth, Hermann J .: Medicinal Chemistry: Targets - Drugs - Chemical Biology; 191 tables . 2., completely reworked. and exp. Ed. Dt. Apotheker-Verl, Stuttgart 2010, ISBN 978-3-7692-5002-2 .
↑ R. Stahlmann, H. Lode: Side effects of the newer fluoroquinolones ( Memento from August 1, 2014 in the Internet Archive ) (PDF; 82 kB); In: Chemotherapy Journal 1998, 7 (3), pp. 107-116.
^ EMA: Norfloxacin , 2008.
↑ BfArM: Decision on the authorization of human medicinal products with the active ingredient norfloxacin , February 5, 2009.

Web links

Entry on norfloxacin at Vetpharm

[Ph._Eur._9-1] European Pharmacopoeia Commission (Ed.): European Pharmacopoeia, 9th edition, 3rd supplement. 2018.

[ChemIDplus-2] Entry on norfloxacin in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on May 21, 2019.

[römpp-3] Entry on norfloxacin. In: Römpp Online . Georg Thieme Verlag, accessed on July 19, 2019.

[rem-4] A ^b D. B. Troy: Remington: The Science and Practice of Pharmacy , p. 1658, 21st edition, Lippincott Raven, 2005, ISBN 0-7817-4673-6 .

[Sigma-5] Data sheet norfloxacin from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).

[6] Schubert-Zsilavecz, Manfred., Roth, Hermann J .: Medicinal Chemistry: Targets - Drugs - Chemical Biology; 191 tables . 2., completely reworked. and exp. Ed. Dt. Apotheker-Verl, Stuttgart 2010, ISBN 978-3-7692-5002-2 .

[stahlmann-7] R. Stahlmann, H. Lode: Side effects of the newer fluoroquinolones ( Memento from August 1, 2014 in the Internet Archive ) (PDF; 82 kB); In: Chemotherapy Journal 1998, 7 (3), pp. 107-116.

[8] EMA: Norfloxacin , 2008.

[9] BfArM: Decision on the authorization of human medicinal products with the active ingredient norfloxacin , February 5, 2009.