Levofloxacin

From Wikipedia, the free encyclopedia

Levofloxacin
Systematic (IUPAC) name
(-)-(S)-9-fluoro-2,3-dihydro-3-methyl-10- (4-methyl-1-piperazinyl)-7-oxo-7H-pyrido [1,2,3-de]-1,4-benzoxazine-6-carboxylic acid
Identifiers
CAS number	100986-85-4
ATC code	J01MA12 S01AX19
PubChem	149096
DrugBank	APRD00477
Chemical data
Formula	C18H20FN3O4
Mol. mass	361.368 g/mol
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	Prescription Only
Routes	Oral, IV, Ophthalmic

Levofloxacin is an advanced generation fluoroquinolone antibiotic, marketed by Ortho-McNeil under the trade name Levaquin in the US. In Europe, it is marketed by Sanofi-Aventis under the trade name of Tavanic, in Chile as Gatigol by Alpes Selection, and in Asia it is marketed by Daiichi under the trade name of Cravit. Levofloxacin was launched in the Japanese market in 1993, and thus has had more than 12 years of testing in efficacy and safety globally. Chemically, levofloxacin is the S-enantiomer (L-isomer) of ofloxacin, and has approximately twice the potency of ofloxacin. It works by inhibiting DNA gyrase, the enzyme that unzips the DNA double helix during bacterial replication.

Levofloxacin is effective against a number of gram-positive and gram-negative bacteria. Because of its broad spectrum of action, levofloxacin is frequently prescribed empirically for a wide range of infections (e.g. pneumonia, urinary tract infection) before the specific causal organism is known. If the causal organism is identified, levofloxacin may be discontinued and the patient may be switched to an antibiotic with a narrower spectrum of activity. Levofloxacin is currently the only respiratory fluoroquinolone approved by the US FDA for the treatment of nosocomial pneumonia.

As approved by the US FDA.

[edit] Gram-positive bacteria

• Enterococcus faecalis (many strains are only moderately susceptible)
• Staphylococcus aureus (methicillin-susceptible strains)
• Staphylococcus epidermidis (methicillin-susceptible strains)
• Staphylococcus saprophyticus
• Streptococcus pneumoniae (including Multidrug-resistant strains, MDRSP)
• Streptococcus pyogenes

[edit] Gram-negative bacteria

• Enterobacter cloacae
• Klebsiella pneumoniae
• Pseudomonas aeruginosa
• Escherichia coli
• Legionella pneumophila
• Serratia marcescens
• Haemophilus influenzae
• Moraxella catarrhalis
• Haemophilus parainfluenzae
• Proteus mirabilis
• Campylobacter

[edit] Other

• Chlamydia pneumoniae
• Mycoplasma pneumoniae
• Peptostreptococcus sp.

• More bacterial coverage is available as per prescribing information for levofloxacin in Japan (Cravit)

v • d • e Quinolones (J01M)
Fluoroquinolones	Ciprofloxacin, Enoxacin, Fleroxacin, Gatifloxacin, Gemifloxacin, Grepafloxacin, Levofloxacin, Lomefloxacin, Moxifloxacin, Norfloxacin, Ofloxacin, Pefloxacin, Prulifloxacin, Rufloxacin, Sparfloxacin, Temafloxacin, Trovafloxacin, Sitafloxacin
Other quinolones	Cinoxacin, Flumequine, Nalidixic acid, Oxolinic acid, Pipemidic acid, Piromidic acid, Rosoxacin