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Quinolone antibiotic

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Quinolone antibiotic
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Ciprofloxacin. A fluoroquinolone medication, commonly used for respiratory and urinary infections.
Clinical data
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administration		Oral
Pharmacokinetic data
MetabolismLiver
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DrugBank
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ECHA InfoCard

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]

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]

Quinolone Antibiotic Media

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

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    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.

References

  1. ↑ 1.0 1.1 1.2 Martens, Evan. Chapter 7 - An Overview of the Industrial Aspects of Antibiotic Discovery (in en). Microbial Resources (2017-01-01)Academic Press. p. 149–168. ISBN 978-0-12-804765-1. Retrieved 2023-07-04.
  2. ↑ 2.0 2.1 2.2 Pham, Thu D. M.. Quinolone antibiotics (in en). MedChemComm 10 (10) (2019-10-16). p. 1719–1739. doi:10.1039/C9MD00120D.
  3. ↑ 3.0 3.1 Kocsis, Bela. Chemical structure and pharmacokinetics of novel quinolone agents represented by avarofloxacin, delafloxacin, finafloxacin, zabofloxacin and nemonoxacin. Annals of Clinical Microbiology and Antimicrobials 15 (1) (2016-05-23). p. 34. doi:10.1186/s12941-016-0150-4.
  4. ↑ 4.0 4.1 4.2 Redgrave, Liam S.. Fluoroquinolone resistance: mechanisms, impact on bacteria, and role in evolutionary success. Trends in Microbiology 22 (8) (August 2014). p. 438–445. doi:10.1016/j.tim.2014.04.007.
  5. ↑ King, D. E.. New classification and update on the quinolone antibiotics. American Family Physician 61 (9) (2000-05-01). p. 2741–2748.
  6. ↑ Thai, Tony. Ciprofloxacin. StatPearls (2023). Treasure Island (FL): StatPearls Publishing. Retrieved 2023-07-04.
  7. ↑ Baggio, Diva. Fluoroquinolone antibiotics and adverse events. Australian Prescriber 44 (5) (2021-10-01). p. 161–164. doi:10.18773/austprescr.2021.035.
  8. ↑ Walker, Randall C.. The Fluoroquinolones. Mayo Clinic Proceedings 74 (10) (October 1999). p. 1030–1037. doi:10.4065/74.10.1030.

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