Ciprofloxacin: review on developments in synthetic, analytical, and medicinal aspects

Figures & data

Figure 1.  Structure of ciprofloxacin.

Table 1.  Major brands of ciprofloxacin in some countries^13,14.

Name of country	Brand name of ciprofloxacin
Australia	C-Flox, Ciloquin, Ciloxan, Ciprol, Ciproxin, Profloxin, Proquin
Canada	Ciloxan, Cipro
Ireland	Biofloxcin, Cifloxager, Ciproxin, Profloxin, Truoxin
New Zealand	Ciloxan, Cipflox, Ciproxin, Topistin, Ufexil
South Africa	Adco-Ciprin, Biocip, Cifloc, Cifran, Ciloxan, Ciploxx, Cipro-Hexal, Ciprobay, Ciprogen, Dynafloc, Orpic, Spec-Topistin
United Kingdom	Ciloxan, Ciproxin
United States	Ciloxan, Cipro
India	Ciloxan, Cipro, Cifran, Ciplox

Figure 2.  Ciprofloxacin derivative (a).

Figure 3.  Ciprofloxacin derivative (b).

Figure 4.  Ciprofloxacin derivatives (c) and (d).

Figure 5.  Ciprofloxacin derivatives (e) and (f).

Figure 6.  Ciprofloxacin derivative (g).

Figure 7.  Ciprofloxacin derivative (h).

Figure 8.  Ciprofloxacin derivative (i).

Figure 9.  Ciprofloxacin derivative (j).

Figure 10.  Ciprofloxacin derivative (k).

Figure 11.  Ciprofloxacin derivative (l).

Figure 12.  Ciprofloxacin derivative (m).

Figure 13.  Ciprofloxacin derivative (n).

Figure 14.  Ciprofloxacin derivative (o).

Figure 15.  Ciprofloxacin derivative (p).

Table 2.  Pharmacokinetic properties of ciprofloxacin^82,86–88.

Pharmacokinetic Parameter	Value
Elimination half-life (h)	4.16
Oral bioavailability	70–80%
Maximum drug concentration in plasma (mg/L)	0.56
Area under the curve (µg h/mL)	2.56
Primary route of excretion	Renal
Time to peak (h)	1.1
Plasma protein binding (%)	20–40%
Renal clearance (L/h)	21.4
Disposition (% of dose)
Renal	40–60
Fecal/biliary	15
Metabolized	10–15

Table 3.  Incidences of adverse events with ciprofloxacin⁸⁷.

Adverse event	Percentage occurrence
Nausea	5.2
Diarrhea	2.3
Taste perversion	0.02
Headache	1.2
Dizziness	<1.0
Phototoxicity	0.4

Table 4.  Summarized uses of ciprofloxacin in infectious diseases^{13,14,109–119}.

Clinical indication	Infection-causing organisms
Urinary tract infections	Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Serratia marcescens, Proteus mirabilis, Providencia rettgeri, Morganella morganii, Citrobacter diversus, Citrobacter freundii, Pseudomonas aeruginosa, Staphylococcus epidermidis, Staphylococcus saprophyticus, or Enterococcus faecalis
Acute uncomplicated cystitis in females	Escherichia coli or Staphylococcus saprophyticus
Chronic bacterial prostatitis	Escherichia coli or Proteus mirabilis
Lower respiratory tract infections	Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Proteus mirabilis, Pseudomonas aeruginosa, Haemophilus influenzae, Haemophilus parainfluenzae, or Streptococcus pneumoniae
Acute sinusitis	Haemophilus influenzae, Streptococcus pneumoniae, or Moraxella catarrhalis
Skin and skin structure infections	Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Proteus mirabilis, Proteus vulgaris, Providencia stuartii, Morganella morganii, Citrobacter freundii, Pseudomonas aeruginosa, Staphylococcus aureus (methicillin-susceptible), Staphylococcus epidermidis, or Streptococcus pyogenes
Bone and joint infections	Enterobacter cloacae, Serratia marcescens, or Pseudomonas aeruginosa
Infectious diarrhea	Escherichia coli (enterotoxigenic strains), Campylobacter jejuni, Shigella boydii^a, Shigella dysenteriae, Shigella flexneri, or Shigella sonnei
Typhoid fever	Salmonella typhi
Uncomplicated cervical and urethral gonorrhea	Neisseria gonorrhoeae
Pyelonephritis	Escherichia coli

^aWhen antibacterial therapy is indicated.

Ciprofloxacin. http://en.wikipedia.org/w/index.php?title=Ciprofloxacin&oldid=287777716. Accessed 6 May 2009.

 Google Scholar

Cipro. Bayer response 12 Feb 2009. http://www.fda.gov/cder/foi/label/2009/019537s69,19847s43,19857s50,20780s27lbl.pdf. Accessed 6 May 2009.

 Google Scholar

Egle JL. Principles of Pharmacology: Basic Concepts and Clinical Applications. New York: Chapman & Hall, 1996:1339–50.

 Google Scholar

Sharma PC, Saneja A, Jain S. Norfloxacin: a therapeutic review. Int J Chem Sci 2008;6:1702–13.

 Google Scholar