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Levofloxacin
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| Systematic (IUPAC) name | |
| (3S)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7- oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ijquinoline- 6-carboxylic acid | |
| Identifiers | |
| CAS number | |
| ATC code | J01 S01 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C18H20FN3O4 |
| Mol. mass | 361.368 g/mol |
| SMILES | & |
| Pharmacokinetic data | |
| Bioavailability | 99% |
| Protein binding | 24 to 38% |
| Metabolism | Renal |
| Half life | 6 to 8 hours |
| Excretion | Urinary |
| Therapeutic considerations | |
| Pregnancy cat. |
C (United States) |
| Legal status | |
| Routes | Oral, IV, ophthalmic |
Levofloxacin is a third-generation fluoroquinolone antibiotic, marketed by Ortho-McNeil under the trade name Levaquin in the United States. In Europe, it is marketed by Sanofi-Aventis under the trade name Tavanic, in Chile as Gatigol by Alpes Selection, in India under the trade name Lebact marketed by Nicolas Piramal and in Asia it is marketed by Xeno Pharmaceuticals as Terlev and by Daiichi under the trade names Cravit and Levox. Generics are also widely available in most countries; other manufacturers include Novell Pharmaceutical Laboratories (Levores). Levofloxacin was launched in the Japanese market in 1993, and was approved by the U.S. Food and Drug Administration on December 20, 1996. Chemically, levofloxacin is the S-enantiomer (L-isomer) of ofloxacin, and has approximately twice the potency of ofloxacin—because the R+enantiomer (D-isomer) of ofloxacin is essentially inactive—and substantially less toxicity. Like other fluoroquinolones, it works by inhibiting DNA gyrase, an enzyme that negatively supercoils DNA.
Levofloxacin is one of the so-called respiratory quinolones, which are effective against a number of Gram-positive and Gram-negative bacteria and, specifically, against the organisms that cause atypical pneumonia. Because of its broad spectrum of action, levofloxacin is frequently prescribed empirically for a wide range of infections (such as pneumonia and urinary tract infection) before the causal organism is known; if and when the causal organism is identified, levofloxacin may be replaced by an antibiotic that has a narrower spectrum of activity. Levofloxacin is currently the only respiratory quinolone approved by the FDA for the treatment of nosocomial pneumonia.
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Susceptible organisms
Gram-positive bacteria
- Enterococcus faecalis (many strains are only moderately susceptible)
- Staphylococcus aureus (resistance is common, especially in MRSA)
- Staphylococcus epidermidis (resistance is common)
- Staphylococcus saprophyticus
- Streptococcus pneumoniae (including Multidrug-resistant strains, MDRSP)
- Streptococcus pyogenes
Gram-negative bacteria
Other
Adverse effects
The side effects of levofloxacin are similar to those of other fluoroquinolone antibiotics. The most common adverse effects are headache, nausea and diarrhea.1 Serious, rare side effects (also common to all fluoroquinolones) include: tendon damage, known as quinolone-induced tendonopathy; irreversible peripheral neuropathy; QT prolongation; central nervous system effects such as dizziness, insomnia, anxiety, tremors, and even hallucinations and seizures; and abnormal blood sugar levels (hypoglycemia and hyperglycemia, even in people who do not have diabetes).12
Levofloxacin crosses the placenta, and fluoroquinolones have been shown to cause fetal harm in animals; it is therefore not recommended for use by pregnant women. It also passes into breast milk, and should not be used by women who are breastfeeding.1
Tendon rupture
As with all fluoroquinolones, there are numerous documented cases of spontaneous tendon rupture, most often of the Achilles tendon.345678 Such ruptures may occur both during therapy and long after therapy has been discontinued; there are documented cases where such ruptures have occurred over a year later. The risk of tendon damage is greater in people taking corticosteroids and in the elderly.9
Since July 2008, all systemic fluoroquinolones (those taken internally, not as eye drops or ear drops) available in the United States must carry a boxed warning warning of the risk of tendon damage.9
References
- ^ a b c Lexi-Comp (August 2008). "Levofloxacin". The Merck Manual Professional. Retrieved on October 10, 2008.
- ^ Mohr JF, McKinnon PS, Peymann PJ, Kenton I, Septimus E, Okhuysen PC (October 2005). "A retrospective, comparative evaluation of dysglycemias in hospitalized patients receiving gatifloxacin, levofloxacin, ciprofloxacin, or ceftriaxone". Pharmacotherapy 25 (10): 1303–9. doi:. PMID 16185173.
- ^ Maurin N (February 2008). "[Fluoroquinolone-induced Achilles tendon rupture]" (in German). Deutsche medizinische Wochenschrift (1946) 133 (6): 241–4. doi:. PMID 18236349.
- ^ Mehlhorn AJ, Brown DA (November 2007). "Safety concerns with fluoroquinolones". The Annals of Pharmacotherapy 41 (11): 1859–66. doi:. PMID 17911203.
- ^ Ng WF, Naughton M (2007). "Fluoroquinolone-associated tendinopathy: a case report". Journal of Medical Case Reports 1: 55. doi:. PMID 17645801. PMC: 1950514, http://www.jmedicalcasereports.com/content/1/1/55.
- ^ Salvi, A E (2007). "Spontaneous bilateral Achilles tendon upture in a patient treated with oral levofloxacin". Journal of Orthopaedics and Traumatology 8 (2): 86. doi:.
- ^ Haddow LJ, Chandra Sekhar M, Hajela V, Gopal Rao G (March 2003). "Spontaneous Achilles tendon rupture in patients treated with levofloxacin". The Journal of Antimicrobial Chemotherapy 51 (3): 747–8. PMID 12615887, http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=12615887.
- ^ Gold L, Igra H (2003). "Levofloxacin-induced tendon rupture: a case report and review of the literature". The Journal of the American Board of Family Practice 16 (5): 458–60. PMID 14645337, http://www.jabfm.org/cgi/pmidlookup?view=long&pmid=14645337.
- ^ a b U.S. Food and Drug Administration (July 8, 2008). "FDA Requests Boxed Warnings on Fluoroquinolone Antimicrobial Drugs". Press release. Retrieved on October 11, 2008.
External inks
- Levaquin information from RxList
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Wikipedia content modification information:
- This page was last modified on 29 November 2008, at 10:44.
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