Moxifloxacin

Structural formula
General
Non-proprietary name	Moxifloxacin
other names	1-cyclopropyl-6-fluoro-8-methoxy-7 - [(4a S , 7a S ) -octahydro-6 H -pyrrolo [3,4- b ] pyridin-6-yl] -4-oxo-1,4 -dihydroquinoline-3-carboxylic acid
Molecular formula	C 21 H 24 FN 3 O 4
External identifiers / databases
CAS number 151096-09-2 (moxifloxacin) 186826-86-8 (moxifloxacin hydrochloride ) EC number 604-773-0 ECHA InfoCard 100.129.459 PubChem 152946 ChemSpider 134802 DrugBank DB00218 Wikidata Q424940
Drug information
ATC code	J01 MA14 , S01 AE07
Drug class	antibiotic
Mechanism of action	Gyrase inhibitors
properties
Molar mass	401.43 g mol −1
Melting point	203–208 ° C (decomposition) (moxifloxacin) 324–325 ° C (decomposition) (moxifloxacin hydrochloride )
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Hydrochloride no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	1320 mg kg −1 ( LD 50 ,  rat ,  oral , hydrochloride)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Moxifloxacin is a medicinal substance, more precisely an antibiotic from the group of the fourth generation of fluoroquinolones ( gyrase inhibitors ) and is subject to a doctor's prescription .

Mode of action

The mechanism of action of moxifloxacin is identical to that of other fluoroquinolones, but it binds to two topoisomerases and thus has two points of attack. Quinolones in general bind to the gyrase , whereby it is inhibited. The binding of the fluoroquinolones to the gyrase creates stable complexes that trigger a multitude of enzymatic reactions that ultimately lead to the death of the bacterial cell . The exact bactericidal mechanism of action of the fluoroquinolones has not yet been clarified.

application

Moxifloxacin is used therapeutically in the case of worsening of a long-standing (chronic) bronchitis , pneumonia and acute inflammation of the paranasal sinuses . However, moxifloxacin should no longer be used as the drug of first choice for these indications. The reason given is that the respiratory tract infections mentioned are predominantly self-limiting and that moxifloxacin is associated with an increased risk of serious side effects.

Due to the good tissue penetration of the active ingredient, moxifloxacin is also approved for complicated skin and soft tissue infections (such as diabetic feet ).

It is also effective against chlamydial infections and other atypical germs such as mycoplasma and legionella . The effectiveness against Haemophilus influenzae and Moraxella catarrhalis is very good, as with all quinolones, and excellent against pneumococci . Moxifloxacin does not work against Pseudomonas aeruginosa ("Pseudomonas gap").

Side effects

Common side effects of moxifloxacin (1–10%) are gastrointestinal disorders, especially nausea, diarrhea, vomiting and indigestion , headache and drowsiness, superinfections caused by resistant bacteria or fungi, and QT prolongation with the risk of dangerous cardiac arrhythmias v. a. with known hypokalaemia and increased liver values . Psychiatric symptoms, changes in the blood count or allergies are less common. Very rare (<1 / 10,000), but particularly serious, are fulminant hepatitis up to life-threatening liver failure and bullous skin reactions such as Stevens-Johnson syndrome or possibly life-threatening toxic epidermal necrolysis . Cases of tendinitis following administration of moxifloxacin and other fluoroquinolones have also been reported. According to clinical studies from Germany and the USA, the incidence of side effects of moxifloxacin is 25%. Side effects can be delayed, persist after discontinuation, intensify over time, and cause permanent disability. Compared to other common antibiotics, fluoroquinolones are responsible for most of the permanent disabilities.

Restricted use by the European Medicines Agency

In 2008, the European Medicines Agency ( EMA) restricted the use of moxifloxacin to cases where other antibiotics could not be used because of the unfavorable risk-benefit ratio. Only the oral dosage form is affected by the restriction of use. The decision of the EMA was preceded by a Rote-Hand-Brief on liver damage and life-threatening skin reactions, some of which were fatal. In addition to the restriction of use in the case of acute exacerbations of chronic bronchitis, acute bacterial sinusitis and pneumonia, the EMA recommended the inclusion of stronger warnings in the instructions for use and specialist information on medicinal products containing moxifloxacin. Thereupon another Rote-Hand-Brief appeared with corresponding restrictions of indications and new indications of increased cardiac risks in women and elderly patients, temporary loss of consciousness, worsening of the symptoms of an existing myasthenia gravis and rhabdomyolysis .

Trade names

Monopreparations

Actira (A), Avalox (D, CH), Avelox (A), Octegra (A), Vigamox (D, CH), Avelon ( South Africa ) and generics (D, A), Zivlox (Morocco)

Individual evidence

1. ↑ ^{a b} The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1087, ISBN 978-0-911910-00-1 .
2. ↑ Moxifloxacin hydrochloride data sheet from Sigma-Aldrich , accessed on May 5, 2011 ( PDF ).
3. ↑ Data sheet MOXIFLOXACIN HYDROCHLORIDE CRS (PDF) at EDQM , accessed on June 14, 2009.
4. ↑ David C. Hooper: Mechanisms of Action of Antimicrobials: Focus on Fluoroquinolones . In: Clinical Infectious Diseases . tape 32 , Supplement_1, March 15, 2001, p. S9-S15 , doi : 10.1086 / 319370 .
5. ↑ Karl Drlica, Muhammad Malik, Robert J. Kerns, Xilin Zhao: quinolone-Mediated Bacterial Death . In: Antimicrobial Agents and Chemotherapy . tape 52 , no. 2 , February 1, 2008, p. 385-392 , doi : 10.1128 / aac.01617-06 , PMID 17724149 .
6. ↑ BfArM - Risk Assessment Procedure - Moxifloxacin (Actimax®, Actira®, Avalox®): Restrictions on use and additional warnings adopted. Retrieved March 12, 2018 . 
7. ↑ C. Joukhadar, H. Stass, U. Müller-Zellberg, E. Lackner, F. Kovar: Penetration of moxifloxacin into healthy and inflamed subcutaneous adipose tissues in humans . In: Antimicrobial Agents and Chemotherapy . tape 47 , no. 10 , 2003, p. 3099-3103 , PMID 14506015 .
8. ↑ technical information Avelox, accessed on July 4, 2015.
9. ↑ ^{a b} Moxifloxacin (Avalox® and Actimax®): New risk information on serious adverse effects (hepatotoxicity and bullous skin reactions). Federal Institute for Drugs and Medical Devices (BfArM), February 12, 2008, accessed on July 15, 2013 . 
10. ↑ O. Burkhardt, T. Köhnlein u. a .: Recurrent tendinitis after treatment with two different fluoroquinolones . In: Scandinavian Journal of Infectious Diseases . tape 36 , no. 4 , 2004, p. 315-316 , PMID 15198194 .
11. ^ A. De Sarro, G. De Sarro: Adverse reactions to fluoroquinolones. an overview on mechanistic aspects . In: Current Medicinal Chemistry . tape 8 , no. 4 , March 2001, p. 371-384 , PMID 11172695 .
12. ↑ Peter Ball: Efficacy and safety of levofloxacin in the context of other contemporary fluoroquinolones: a review . In: Current Therapeutic Research, Clinical and Experimental . tape 64 , no. 9 , November 2003, p. 646-661 , doi : 10.1016 / j.curtheres.2003.11.003 , PMID 24944413 , PMC 4053061 (free full text).
13. ↑ Drug Safety and Availability - FDA Drug Safety Communication: FDA updates warnings for oral and injectable fluoroquinolone antibiotics due to disabling side effects ( en )
14. ↑ FDA: FDA / CDER Drug Information Webinar - Fluoroquinolone Safety Labeling Changes. In: www.fda.gov. FDA, April 2017, accessed January 22, 2019 . 
15. ↑ Moxifloxacin. Retrieved July 4, 2015 . 
16. ↑ EMEA significantly restricts the use of moxifloxacin and norfloxacin. (No longer available online.) In: aerzteblatt.de. July 25, 2008, archived from the original on July 13, 2015 ; Retrieved July 4, 2015 . Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice.  
17. ↑ BfArM - Rote-Hand-Letters and Information Letters - Rote-Hand-Brief on Avalox®, Octegra®, Actimax®, Actira®: restriction of the indications. Retrieved March 14, 2018 . 

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 !