What is the Difference Between Ciprofloxacin and Ofloxacin

The key difference between Ciprofloxacin and Ofloxacin is that Ciprofloxacin contains a piperazine ring at the C7 position and a single fluorine atom at the C6 position, while Ofloxacin lacks a piperazine ring and has two fluorine atoms at the C2 and C6 positions.

Ciprofloxacin and Ofloxacin are both fluoroquinolone antibiotics prescribed to treat similar types of infections, including urinary tract infections, respiratory tract infections, skin and soft tissue infections, bone and joint infections, and certain sexually transmitted infections like gonorrhea. These antibiotics work by inhibiting the activity of bacterial DNA gyrase and topoisomerase IV enzymes. By doing so, they interfere with bacterial DNA replication and repair, ultimately leading to bacterial cell death. However, bacterial resistance can be developed due to their widespread use. Therefore, it is essential to use these antibiotics judiciously to minimize the development of resistance. Local antibiotic resistance patterns may influence the choice between the two.

CONTENTS

1. Overview and Key Difference
2. What is Ciprofloxacin 
3. What is Ofloxacin
4. Similarities – Ciprofloxacin and Ofloxacin
5. Ciprofloxacin vs. Ofloxacin in Tabular Form
6. Summary – Ciprofloxacin vs. Ofloxacin

What is Ciprofloxacin?

Ciprofloxacin is a fluoroquinolone antibiotic used to treat various bacterial infections such as urinary tract infections, sexually transmitted infections, gastrointestinal infections, lower respiratory tract infections, and pneumonia. The drug was patented in 1983 and approved in 1987 by the FDA. Ciprofloxacin is not approved for neonates worldwide, but it may be prescribed as a salvage therapy for life-threatening infections caused by multi-drug-resistant sepsis. Ciprofloxacin is also shown to be associated with apoptotic and anti-proliferative properties in several carcinomas, including osteosarcoma, leukemia, and bladder cancers. However, these indications should be further confirmed in the clinical setting.

Ciprofloxacin displays antibacterial activity by inhibiting DNA replication, targeting the bacterial DNA topoisomerase IV and DNA-gyrase. After oral administration, 20-40% of the drug is bound with the plasma protein and is distributed with a total volume of distribution of 2-3 L/kg. The drug is primarily metabolized in the liver to oxociprofloxacin and sulociprofloxacin by CYP1A2. The drug is eliminated via urine and feces with a half-life of 4 hours. Ciprofloxacin can be taken with or without food; however, avoiding milk and dairy products is recommended since they can decrease the absorption of Ciprofloxacin. The overdose symptoms include nausea, vomiting, abdominal pain, and oliguria. Commonly found brand names of Ciprofloxacin include Cetraxal, Ciloxan, Otixal, Otovel, and Proquin.

What is Ofloxacin?

Ofloxacin is another fluoroquinolone prescribed to treat gram-positive and gram-negative bacterial infections. Ofloxacin was approved by the FDA in 1990 as an alternative to Ciprofloxacin with improved pharmacokinetics and pharmacodynamic properties. Currently, the drug is available for infections such as respiratory tract, kidney, skin, soft tissue, urinary tract infections, and urethral and cervical gonorrhea. Ofloxacin prevents the supercoiling of bacterial DNA by inhibiting the DNA topoisomerase IV and DNA gyrase enzymes. The inhibition of these topoisomerases leads to the inhibition of the cell division of bacteria.

Ofloxacin reaches the maximum serum concentration within 1-2 hours after oral administration with 98% bioavailability. Approximately 32% of the absorbed drug remains bound with plasma proteins while distributed to the target sites. The drug then undergoes hepatic metabolism and is mainly eliminated by renal excretion, with an elimination half-life of 9 hours. Ofloxacin can also be taken with or without food; however, limiting the caffeine during treatment is advised. The brand names of Ofloxacin include Floxstat and Zanocin.

What are the Similarities Between Ciprofloxacin and Ofloxacin?

• Ciprofloxacin and Ofloxacin are both fluoroquinolone antibiotics.
• Both Ciprofloxacin and Ofloxacin are broad-spectrum antibiotics.
• They work by inhibiting the activity of bacterial topoisomerase IV enzymes and DNA gyrase.
• These antibiotics are prescribed to treat similar infections.
• They share common side effects, such as nausea, vomiting, diarrhea, headache, and dizziness.
• Bacterial resistance can develop against Ciprofloxacin and Ofloxacin due to their widespread use.

What is the Difference Between Ciprofloxacin and Ofloxacin?

Ciprofloxacin and Ofloxacin are fluoroquinolones prescribed against a wide range of bacteria, including gram-negative and gram-positive bacteria. However, there is a significant difference between Ciprofloxacin and Ofloxacin. Ciprofloxacin contains a piperazine ring at the C7 position and a single fluorine atom at the C6 position. In contrast, Ofloxacin lacks a piperazine ring and has two fluorine atoms at the C2 and C6 positions. The brand names of Ciprofloxacin include Cetraxal, Ciloxan, Otixal, Otovel, and Proquin, while Ofloxacin is typically sold as Floxstat and Zanocin.

Furthermore, Ciprofloxacin has a shorter half-life and is primarily eliminated by both the kidneys and the liver. In comparison, Ofloxacin has a half-life of 9 hours and is primarily eliminated by kidneys. Ciprofloxacin is available as an intravenous solution, oral powder for reconstitution, oral tablet, oral tablet, and extended-release, while Ofloxacin is available as an oral tablet.

Below is a summary of the difference between Ciprofloxacin and Ofloxacin in tabular form for side-by-side comparison.

Summary – Ciprofloxacin vs. Ofloxacin

Ciprofloxacin and Ofloxacin are fluoroquinolones prescribed to treat various bacterial infections. The key difference between Ciprofloxacin and Ofloxacin is their structure. Ciprofloxacin contains a piperazine ring at the C7 position and a single fluorine atom at the C6 position, while Ofloxacin lacks a piperazine ring and has two fluorine atoms at the C2 and C6 positions. They work by inhibiting the activity of bacterial topoisomerase IV enzymes and DNA gyrase to prevent bacterial growth. However, recent evidence suggests bacterial resistance can develop against Ciprofloxacin and Ofloxacin due to their widespread use. It is important to note that both Ciprofloxacin and Ofloxacin can cause serious side effects, such as nausea, vomiting, diarrhea, headache, and dizziness. The choice of antibiotic will depend on the specific infection being treated and the patient’s circumstances.

Reference:

1. Sharma, Prabodh Chander, et al. “Ciprofloxacin: Review on developments in synthetic, analytical, and medicinal aspects.” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 25, no. 4, 2010, pp. 577–589.
2. WILTON, L. V., et al. “A comparison of ciprofloxacin, norfloxacin, ofloxacin, azithromycin and Cefixime examined by observational cohort studies.” British Journal of Clinical Pharmacology, vol. 41, no. 4, 1996, pp. 277–284.

Image Courtesy:

1. “Ciprofloxacin” By Fvasconcellos – Own work (Public Domain) via Commons Wikimedia
2. “Ofloxacin” By Fvasconcellos 02:55, 14 May 2007 (UTC) – Own work (Public Domain) via Commons Wikimedia