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Fluoroquinolones


Fluoroquinolones are a group of chemical substances used for antibiotic treatment of bacterial infection.[1] They can be used to treat many different infections, since they work against gram-positive and gram-negative bacteria, the two main types of bacteria.[2] Benefits of using fluoroquinolones for treatment include their ease of access, simple formulas, large amount of bacterial targets, effectiveness against infection, and unlikely chance of side effects.[2]

Fluoroquinolone
Chemical structure of Ciprofloxacin
Ciprofloxacin. A fluoroquinolone medication, commonly used for respiratory and urinary infections.
Clinical data
Routes of
administration		Oral
Pharmacokinetic data
MetabolismLiver
Identifiers
DrugBank
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}

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Nomenclature and structure

Fluoroquinolones are a sub-class of quinolone antibiotics, named for their chemical structure. Fluoroquinolones have a similar structure to quinolones; two fused carbohydrate rings with a fluorine atom attached to the sixth carbon and a nitrogen atom replacing the eighth carbon atom.[1][2][3][4]

Medicine

The following medicines are fluoroquinolone antiobiotics:[5]

  • Norfloxacin (Norocin)
  • Lomefloxacin (Maxaquin)
  • Enoxacin (Penetrex)
  • Ofloxacin (Floxin)
  • Ciprofloxacin (Cipro)
  • Levofloxacin (Levaquin)
  • Sparfloxacin (Zagam)
  • Gatifloxacin (Tequin)
  • Moxifloxacin (Avelox)
  • Trovafloxacin (Trovan)
  • Alatrofloxacin (Trovan IV)

Ciproflaxin is the most frequently prescribed fluoroquinolone antibiotic, for its strength against gram-negative bacilli bacteria such as Escherichia coli and Salmonella.[3][6]

Mechanism of action

Fluoroquinolones kill bacteria by damaging their DNA, through halting enzyme function. Enzymes Topoisomerase I and IV are affected such that the supercoiling of bacterial genetic material is not functional.[4]

Side effects

The following side effects can occur during fluoroquinolone antibiotic treatment:[1][7]

  • retinal damage
  • Achilles tendon damage
  • Nerve disfunction (peripheral neuropathy)
  • psychiatric change (central neuropathy)
  • diarrhea

Bacterial resistance

A growing number of bacteria are becoming resistant to quinolone antibiotics due to overuse.[8] To slow the spread of bacterial resistance, fluoroquinolones are usually used as treatment after specific antibiotic medicines have been ruled out.[4]

Fluoroquinolones Media

  • Skeletal formula of levofloxacin. Created using ACD/ChemSketch 10.0, Inkscape, and vim.

  • Chemical structure of trovafloxacin

  • Structure of bacterial DNA gyrase complexed with DNA and two ciprofloxacin molecules (green)

  • Nalidixic acid. Although technically a naphthyridine, it is considered the predecessor of all subsequently developed quinolone antibiotics.

  • Sites of substitution in second-generation fluoroquinolone antibiotics: Here, and in following the orientation of the quinolones are flipped with respect to horizontal and vertical axes, relative to earlier images; the nitrogen (N)-containing pyridine ring is now on the left, and the N-1 atom and C-6 carbonyl are at 12 o'clock and 6 o'clock in the pyridine ring. The characteristic 6-fluoro group is shown in red.

References

  1. ↑ 1.0 1.1 1.2 Martens, Evan; Demain, Arnold L. (2017-01-01), Kurtböke, Ipek (ed.), "Chapter 7 - An Overview of the Industrial Aspects of Antibiotic Discovery", Microbial Resources, Academic Press, pp. 149–168, ISBN 978-0-12-804765-1, retrieved 2023-07-04
  2. ↑ 2.0 2.1 2.2 Pham, Thu D. M.; Ziora, Zyta M.; Blaskovich, Mark A. T. (2019-10-16). "Quinolone antibiotics". MedChemComm. 10 (10): 1719–1739. doi:10.1039/C9MD00120D. ISSN 2040-2511. PMC 6836748. PMID 31803393.
  3. ↑ 3.0 3.1 Kocsis, Bela; Domokos, J.; Szabo, D. (2016-05-23). "Chemical structure and pharmacokinetics of novel quinolone agents represented by avarofloxacin, delafloxacin, finafloxacin, zabofloxacin and nemonoxacin". Annals of Clinical Microbiology and Antimicrobials. 15 (1): 34. doi:10.1186/s12941-016-0150-4. ISSN 1476-0711. PMC 4878067. PMID 27215369.
  4. ↑ 4.0 4.1 4.2 Redgrave, Liam S.; Sutton, Sam B.; Webber, Mark A.; Piddock, Laura J.V. (August 2014). "Fluoroquinolone resistance: mechanisms, impact on bacteria, and role in evolutionary success". Trends in Microbiology. 22 (8): 438–445. doi:10.1016/j.tim.2014.04.007. ISSN 0966-842X.
  5. ↑ King, D. E.; Malone, R.; Lilley, S. H. (2000-05-01). "New classification and update on the quinolone antibiotics". American Family Physician. 61 (9): 2741–2748. ISSN 0002-838X. PMID 10821154.
  6. ↑ Thai, Tony; Salisbury, Blake H.; Zito, Patrick M. (2023), "Ciprofloxacin", StatPearls, Treasure Island (FL): StatPearls Publishing, PMID 30571075, retrieved 2023-07-04
  7. ↑ Baggio, Diva; R Ananda-Rajah, Michelle (2021-10-01). "Fluoroquinolone antibiotics and adverse events". Australian Prescriber. 44 (5): 161–164. doi:10.18773/austprescr.2021.035. PMC 8542490. PMID 34728881.
  8. ↑ Walker, Randall C. (October 1999). "The Fluoroquinolones". Mayo Clinic Proceedings. 74 (10): 1030–1037. doi:10.4065/74.10.1030. ISSN 0025-6196.
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