Ciprofloxacin Drug - Medicinal Chemistry & Uses

By: Pharma Tips | Views: 2421 | Date: 21-Oct-2011

Ciprofloxacin is a member of the antibiotic class Quinolones. The presence of a fluorine group at position 6 of the molecule places it into a subclass called the Fluoroquinolones. Ciprofloxacin shows good bioavailability, so it can be used orally as well as parenterally, although its bioavailability is not as good as some other members of this class.



Introduction to Ciprofloxacin

             Ciprofloxacin is a member of the antibiotic class Quinolones. The presence of a fluorine group at position 6 of the molecule places it into a subclass called the Fluoroquinolones. Ciprofloxacin shows good bioavailability, so it can be used orally as well as parenterally, although its bioavailability is not as good as some other members of this class. It is a broad spectrum antibiotic that is widely used in clinical practice for many common afflictions including urinary tract and respiratory tract infections. (For more information on indications, please see the Clinical Uses section.)

Ciprofloxacin

Mechanism of Action

            The Fluoroquinolones are bactericidal, meaning that they kill the bacteria cell. They act to inhibit DNA Gyrase, the enzyme responsible for the supercoiling and packing, and thus replication and transcription, of DNA in bacteria. Fluoroquinolones also inhibit Topoisomerase IV, an enzyme involved in DNA replication and cell division. Since these agents do not bind to human Topoisomerases, they are not toxic to the patient.

Resistance

            The most common method of resistance to Quinolones is enzyme mutation that leads to a decrease in susceptibility of the bacteria to the antibiotic. This mechanism of resistance has not been a major problem with the Fluoroquinolones. The dual-enzyme mechanism of action of these antibiotics helps to decrease the incidence of resistance, since a bacterial cell would have to possess mutated forms of two different enzymes to be insensitive to the medication. A second method of resistance is through changes in the cell membrane that would decrease nutrient and other uptake into the cell. This is not as common as the first method, but may be a problem that is much more serious and harder to correct.

Clinical Uses of Ciprofloxacin

Ciprofloxacin is effective against many aerobic Gram-negative organisms including several Streptococcus and Staphylococcus strains. It is also active against several Gram-positive organisms including Escherichia coli. It has also recently been used for both prophylaxis and treatment of Bacillus anthracis infection. Since the Quinolones have a different mechanism of action from many other antibacterial classes, there is little incidence of cross-resistance between the classes. Therefore, ciprofloxacin and other Quinolones can be used in cases of resistance to other antibiotics.(11)


Doses and Dosing Information

Ciprofloxacin is available as immediate-release tablets in 100mg, 250mg, 500mg, and 750mg strengths. The extended-release formulation is available in 500mg and 1000mg tablets. There is also an oral suspension available in 5% and 10% strengths, an intravenous (IV) formulation, and a 0.3% ophthalmic solution. The formulation, strength and duration of treatment depend on the severity of the infection and the causative organism. For example, the extended-release tablets are only indicated for the treatment of urinary tract infections in adult patients; an uncomplicated infection would be treated with 500mg tablets once daily for 3 days, while a complicated infection would require 1000mg tablets once daily for 7 to 14 days. A severe lower respiratory infection would require 750mg immediate-release tablets every 12 hours for 7 to 14 days; exposure to inhalational anthrax should be treated with 500mg immediate-release tablets every 12 hours for 60 days.(11)

          Ciprofloxacin can be used in pediatrics, but the dosage must be adjusted for the child’s size. When treating a complicated urinary tract infection with immediate-release oral tablets, the normal dosage is 10-20 mg/kg up to a maximum of 750mg every 12 hours for 10 to 21 days. There must also be dosage adjustments made in renally impaired patients, since the main route of elimination of ciprofloxacin is through the kidneys. Such dosages are based on the estimate of the patient’s creatinine clearance.(11)

Adverse Effects

          Ciprofloxacin may have central nervous system (CNS) effects such as dizziness, hallucinations, tremors and depression. It may also cause convulsions and toxic psychosis. As a result of these possible effects, patients already at increased risk for seizures or CNS problems should be closely monitored when taking Quinolones. Anaphylactic reactions are also possible, so patients should be advised to look for symptoms such as itching, dyspnea and pharyngeal or facial edema, and to seek medical help if these symptoms appear. Pseudomembranous colitis can be caused by almost all antibiotics, including Quinolones, so if patients present with diarrhea during or after treatment with ciprofloxacin, proper treatment including fluid and electrolyte replenishment may be required. There have also been reports of rare cases of peripheral neuropathy or tendon weakening following ciprofloxacin treatment.(11)

Drug Interactions

          When taken with food, absorption of ciprofloxacin may be delayed, resulting in an extended time to reach the desired plasma concentration. Ciprofloxacin absorption is also slowed by metals such as magnesium, aluminum, calcium, iron and zinc; as a result, ciprofloxacin must be dosed at least 2 hours before or 6 hours after the administration of antacids or other products containing the aforementioned ingredients. Concomitant administration with omeprazole is also discouraged, since this combination can cause a significant decrease in plasma concentrations of ciprofloxacin.(11)

          Ciprofloxacin is a moderate inhibitor of the hepatic cytochrome P450 1A2 isoenzymes, and as such it can interfere with the metabolism of compounds that are substrates of this particular metabolic pathway. One specific medication that has shown problems with concomitant administration is theophylline, a 1A2 substrate. By inhibiting the isoenzymes, ciprofloxacin will slow the metabolism and therefore increase plasma concentrations of theophylline, which can lead to adverse reactions associated with theophylline toxicity.(12)

The Future of Ciprofloxacin

          Because of the dual mechanism of action of the Quinolones, bacteria need to make two mutations to become resistant to the antibiotic activity. In addition, doctors have tended to use the Quinolones only in cases where the causative organism has been identified as Quinolone-sensitive. As a result, the Quinolones will probably be clinically important antibiotics for years to come.(11)


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