CIPROFLOXACIN

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Ciprofloxacin is a fluoroquinolone antibiotic that is derived from the earlier quinolones. Nalidixic acid is a typical example of a quinolone; and both the quinolones and fluoroquinolones are bacterial DNA replication inhibitors. But antibiotics in the fluoroquinolone family have broader activity than the quinolones. Other examples of fluoroquinolones include ofloxacin, norfloxacin, sparfloxacin, lomefloxacin and levofloxacin. Fluoroquinolones are fluorinated quinolones or newer quinolone antibiotics, and they have superior antibacterial activity than the quinolones (e.g. nalidixic acid).

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SOURCES OF CIPROFLOXACIN

Ciprofloxacin, a fluoroquinolone is a synthetic antibiotic that is produced by chemical modification of the quinolone structure (Figure 1). Both the fluoroquinolones and quinolones are synthetic chemotherapeutic antibacterial agents; and they are not produced naturally by microbes.

Figure 1. Chemical structure of quinolones. Quinolones have a nucleus that is composed of two fused 6-membered rings. Fluoroquinolones are produced from quinolones by a chemical modification of the quinolone nucleus especially by the addition of a fluorine molecule at the carbon-6 of the quinolone nucleus. Photo courtesy: https://www.microbiologyclass.com

STRUCTURE OF QUINOLONES

The structure of quinolones from which fluoroquinolones (e.g. ciprofloxacin) are synthetically derived from is a nucleus of two fused 6-membered rings (Figure 1) that is chemically substituted with a fluorine molecule to form fluoroquinolones. The incorporation of fluorine molecules into the quinolone nucleus gives rise to ciprofloxacin and other fluoroquinolones with an enhanced antibacterial activity. This is why fluoroquinolones are usually more preferred than the quinolones (e.g. nalidixic acid) in clinical medicine. The chemical structures of some fluoroquinolones are shown in Figure 2.    

Figure 2. Chemical structures of some fluoroquinolones. Photo courtesy: Photo courtesy: : https://www.microbiologyclass.com

CLINICAL APPLICATION OF CIPROFLOXACIN

Ciprofloxacin is used to treat bacterial infections caused by Gram-negative and Gram-positive bacteria. They are often used in synergy with other antibacterial agents. The fluoroquinolones (including ciprofloxacin) is used to treat anthrax (caused by B. anthracis). And they are used clinically to treat UTIs, respiratory tract infections, skin infections, and infections caused by anaerobic bacteria and Chlamydia. The quinolones (e.g. nalidixic acid) are basically used to treat UTIs; and they are mainly active against Gram-negative bacteria.  

SPECTRUM OF ACTIVITY OF CIPROFLOXACIN

Ciprofloxacin and other fluoroquinolones have a broad spectrum of activity and they are bactericidal in action. They have activity against both Gram-positive bacteria and Gram-negative bacteria. Quinolones are effective for the treatment of UTIs especially those caused by bacteria in the family Enterobacteriaceae. They are mainly active against some Gram-negative bacteria, and with little or no antibacterial activity against Gram-positive bacteria. 

MECHANISM OR MODE OF ACTION OF CIPROFLOXACIN

Ciprofloxacin and other fluoroquinolones as well as the quinolones are generally known as DNA synthesis inhibitors (Figure 3). They mainly bind to the DNA gyrase enzyme (or topoisomerase II or IV) during bacterial DNA replication. This binding prevents the enzyme (DNA gyrase or topoisomerase IV) from carrying out its biological function of cutting, repairing and coiling DNA molecules during bacterial DNA replication. Once ciprofloxacin binds to the topoisomerase enzyme, the function of DNA gyrase in DNA replication will be inhibited. The target pathogenic bacteria eventually die because the inhibition of DNA synthesis in bacteria blocks cell division. This obstructs other important cellular activities of the organism. 

Figure 3. Major targets of antimicrobial agents. Fluoroquinolones are DNA synthesis inhibitors; and they bind to the enzymes (particularly DNA gyrase or topoisomerase IV) that drive DNA replication in a bacterial cell. Photo courtesy: https://amrls.cvm.msu.edu/pharmacology/antimicrobials/mode-of-action

BACTERIAL RESISTANCE TO CIPROFLOXACIN

Bacterial resistance to the fluoroquinolones and quinolones is usually due to mutation in the chromosome of the organism which makes them to be less-susceptible to the drug. Mutation in the active site or binding site of DNA gyrase enzymes prevents fluoroquinolones or quinolones to bind, and this can make a bacterium to be resistant to the antibiotic. 

PHARMACOKINETICS, SIDE EFFECT/TOXICITY OF CIPROFLOXACIN

Ciprofloxacin and other fluoroquinolones are well distributed in the body after oral distribution. They are excreted in urine and bile through the kidney. Fluoroquinolones and quinolones are contraindicated for pregnant women and infants because the antibiotic damages growing bones and cartilages. Nausea, vomiting, headache and dizziness are some of the mild untoward effects associated with the clinical use of the fluoroquinolones.   

FURTHER READING

Ashutosh Kar (2008). Pharmaceutical Microbiology, 1st edition. New Age International Publishers: New Delhi, India. 

Block S.S (2001). Disinfection, sterilization and preservation. 5th edition. Lippincott Williams & Wilkins, Philadelphia and London.

Courvalin P, Leclercq R and Rice L.B (2010). Antibiogram. ESKA Publishing, ASM Press, Canada.

Denyer S.P., Hodges N.A and Gorman S.P (2004). Hugo & Russell’s Pharmaceutical Microbiology. 7th ed. Blackwell Publishing Company, USA. Pp.152-172.

Ejikeugwu Chika, Iroha Ifeanyichukwu, Adikwu Michael and Esimone Charles (2013). Susceptibility and Detection of Extended Spectrum β-Lactamase Enzymes from Otitis Media Pathogens. American Journal of Infectious Diseases. 9(1):24-29.

Finch R.G, Greenwood D, Norrby R and Whitley R (2002). Antibiotic and chemotherapy, 8th edition. Churchill Livingstone, London and Edinburg.

Russell A.D and Chopra I (1996). Understanding antibacterial action and resistance. 2nd edition. Ellis Horwood Publishers, New York, USA.

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