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Ciprofloxacin

Page under construction - by: John Ripollone, Department of Biological Sciences (in conjunction with the Department of Chemistry and Biochemistry) - Messiah College, Grantham, PA 17027.

General Information

Ciprofloxacin is a broad-spectrum fluoroquinolone antibiotic that is generally effective against both aerobic gram-positive and aerobic gram-negative bacteria^[1]. Bacterial organisms that have been shown to be efficiently targeted by ciprofloxacin are:

Aerobic Gram-Positive Bacteria (With Certain Strain Particularities):

Enterococcus faecalis (many strains are only moderately susceptible), Staphylococcus aureus (methicillin-susceptible strains only), Staphylococcus epidermidis (methicillin-susceptible strains only), Staphylococcus saprophyticus, Streptococcus pneumoniae (penicillin-susceptible strains only), Streptococcus pyogenes

Aerobic Gram-Negative Bacteria:

Campylobacter jejuni, Citrobacter diversus, Citrobacter freundii, Enterobacter cloacae, Escherichia coli, Haemophilus influenzae, Haemophilus parainfluenzae, Klebsiella pneumoniae, Moraxella catarrhalis, Morganella morganii, Neisseria gonorrhoeae, Proteus mirabilis, Proteus vulgaris, Providencia rettgeri, Providencia stuartii, Pseudomonas aeruginosa, Salmonella typhi, Serratia marcescens, Shigella boydii, Shigella dysenteriae, Shigella flexneri, Shigella sonnei

Ciprofloxacin also exhibits in vitro minimum inhibitory concentrations of 1 μg/mL or less against strains of the following bacteria (with less adequate characterizations of the effects of treatment against these bacteria in terms of efficiency and general safety):

Aerobic Gram-Positive Bacteria (With Certain Strain Particularities):

Staphylococcus haemolyticus, Staphylococcus hominis, Streptococcus pneumoniae (penicillin-resistant strains only)

Aerobic Gram-Negative Bacteria:

Acinetobacter Iwoffi, Aeromonas hydrophila, Edwardsiella tarda, Enterobacter aerogenes, Klebsiella oxytoca, Vibrio cholerae, Legionella pneumophila, Vibrio parahaemolyticus, Pasteurella multocida, Vibrio vulnificus, Salmonella enteritidis, Yersinia enterocolitica

Most anaerobic bacteria exhibit Ciprofloxacin-resistance.

The effectiveness of Ciprofloxacin against the anthrax-causing bacteria, Bacillus anthracis - both in vitro and by use of surrogate marker serum levels - has also been demonstrated^[2][3]. Thus, Ciprofloxacin is currently an FDA-approved treatment for patients who have been exposed to anthrax via inhalation^[4]. Likewise, Ciprofloxacin may be used to treat plague (from the bacteria, Yersinia pestis) and tularemia (from the bacteria, Francisella tularensis^[5]. Thus, Ciprofloxacin demonstrates usefulness in the field of counter-bioterrorism given its action against bacteria that could potentially be implemented in biological warfare. Furthermore, in its extended-release tablet form, Ciprofloxacin tends to target, specifically, certain types of urological infections (e.g. epididymitis). The nature of Ciprofloxacin, then, as a powerful, broad-range antibiotic is crucial for broad-range bacterial infection treatment. An understanding of the action of Ciprofloxacin at the molecular level is, no doubt, necessary for an appreciation of the potency of Ciprofloxacin as witnessed at the macro level.

Structure and General Administration

The identification of Ciprofloxacin as a "quinolone" stems from the heterocyclic, bicyclic core-containing structure of Ciprofloxacin, which structure is characteristic of all quinolones^[6].

Ciprofloxacin is administered as CIPRO Oral Suspension (Ciprofloxacin) and as CIPRO Tablets (Ciprofloxacin hydrochloride)^[7]. Both administration types are oral.

CIPRO Oral Suspension (Ciprofloxacin) is a 1-cyclopropyl-6-floro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid with empirical formula: C₁₇H₁₈FN₃O₃. Ciprofloxacin has a molecular weight of 331.35 g/mol and occurs as a yellowish, crystalline substance^[8][9]. A simple molecular structure of Ciprofloxacin is shown (base empirical formula).

^[10]

CIPRO Tablet[s] (Ciprofloxacin hydrochloride) is the monohydrochloride monohydrate salt of 1-cyclopropyl-6-floro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid with empirical formula C₁₇H₁₈FN₃O₃•HCl•H₂O. Ciprofloxacin hydrochloride has a molecular weight of 385.5 g/mol and also occurs as a yellowish, crystalline substance^[11]. A simple molecular structure of Ciprofloxacin hydrochloride is shown (base empirical formula).

^[12]

References

1. ↑ CIPRO® (ciprofloxacin hydrochloride) TABLETS - CIPRO® (ciprofloxacin*) ORAL SUSPENSION - Drug Information Packet. Bayer HealthCare Pharmaceuticals. Schering Plough Corporation.
2. ↑ CIPRO® (ciprofloxacin hydrochloride) TABLETS - CIPRO® (ciprofloxacin*) ORAL SUSPENSION - Drug Information Packet. Bayer HealthCare Pharmaceuticals. Schering Plough Corporation.
3. ↑ 2011. Ciprofloxacin. Medicine Plus. American Society of Health-System Pharmacists Inc. 2011. http://www.nlm.nih.gov/medlineplus/druginfo/meds/a688016.html.
4. ↑ 2001. Information on Cipro (Ciprofloxacin Hydrochloride) for Inhalation Anthrax for Consumers: Questions and Answers. Fda.gov. http://www.fda.gov/Drugs/EmergencyPreparedness/BioterrorismandDrugPreparedness/ucm130711.htm. Last updated, 2009.
5. ↑ 2011. Ciprofloxacin. Medicine Plus. American Society of Health-System Pharmacists Inc. 2011. http://www.nlm.nih.gov/medlineplus/druginfo/meds/a688016.html.
6. ↑ Siegmund, K., et al. (2005). Molecular details of quinolone-DNA interactions: solution structure of an unusuallystable DNA duplex with covalently linked nalidixic acid residues and non-covalent complexes derived from it. Nucleic Acids [Research], 33(15), 4838-4848.
7. ↑ CIPRO® (ciprofloxacin hydrochloride) TABLETS - CIPRO® (ciprofloxacin*) ORAL SUSPENSION - Drug Information Packet. Bayer HealthCare Pharmaceuticals. Schering Plough Corporation.
8. ↑ Molecular weight from Chemexper.com.
9. ↑ CIPRO® (ciprofloxacin hydrochloride) TABLETS - CIPRO® (ciprofloxacin*) ORAL SUSPENSION - Drug Information Packet. Bayer HealthCare Pharmaceuticals. Schering Plough Corporation.
10. ↑ Image from: http://www.google.com/imgres?imgurl=http://textbookofbacteriology.net/themicrobialworld/cipro.gif&imgrefurl=http://textbookofbacteriology.net/themicrobialworld/control.html&usg=__wtzKLHB3NssfnODEB224br5-Bcw=&h=200&w=250&sz=2&hl=en&start=0&zoom=1&tbnid=o7VT7s6FFIUrWM:&tbnh=160&tbnw=199&ei=Hk10TaypBcL58AbyvIjKDw&prev=/images%3Fq%3Dciprofloxacin%26um%3D1%26hl%3Den%26client%3Dfirefox-a%26sa%3DN%26rls%3Dorg.mozilla:en-US:official%26biw%3D1280%26bih%3D647%26tbs%3Disch:1&um=1&itbs=1&iact=hc&vpx=527&vpy=300&dur=1709&hovh=160&hovw=200&tx=155&ty=82&oei=EU10TcvOCMbdtge5msiLDw&page=1&ndsp=16&ved=1t:429,r:7,s:0.
11. ↑ Molecular weight from: CIPRO® (ciprofloxacin hydrochloride) TABLETS - CIPRO® (ciprofloxacin*) ORAL SUSPENSION - Drug Information Packet. Bayer HealthCare Pharmaceuticals. Schering Plough Corporation.
12. ↑ Image from: http://www.google.com/imgres?imgurl=http://images.rxlist.com/images/rxlist/ciloxan_s.gif&imgrefurl=http://www.rxlist.com/ciloxan_ophthalmic_ointment-drug.htm&usg=__UqTKseSe8hD85c5RLGIz2_dbAg0=&h=142&w=232&sz=2&hl=en&start=16&zoom=1&tbnid=70Q2WG5hppsQ5M:&tbnh=100&tbnw=164&ei=T010TenMFYH_8Aa6gvDKDw&prev=/images%3Fq%3Dciprofloxacin%26um%3D1%26hl%3Den%26client%3Dfirefox-a%26sa%3DN%26rls%3Dorg.mozilla:en-US:official%26biw%3D1280%26bih%3D647%26tbs%3Disch:10%2C624&um=1&itbs=1&iact=hc&vpx=1064&vpy=399&dur=309&hovh=106&hovw=174&tx=98&ty=76&oei=EU10TcvOCMbdtge5msiLDw&page=2&ndsp=18&ved=1t:429,r:17,s:16&biw=1280&bih=647.