Stereochemistry | ABSOLUTE |
Molecular Formula | C18H20FN3O4 |
Molecular Weight | 361.3675 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N4CCN(C)CC4
InChI
InChIKey=GSDSWSVVBLHKDQ-JTQLQIEISA-N
InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)/t10-/m0/s1
Molecular Formula | C18H20FN3O4 |
Molecular Weight | 361.3675 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Levofloxacin is the L-isomer of the racemate, ofloxacin, a quinolone antimicrobial agent. Levofloxacin is used for oral and intravenous administration. Levofloxacin is sold under brand name levaquin and is used to treat infections in adults (≥18 years of age) caused by designated, susceptible bacteria such as, pneumonia: nosocomial and community acquired; skin and skin structure infections: complicated and uncomplicated; chronic bacterial prostatitis; inhalational anthrax. In addition this drug is used to treat plague; urinary tract infections: complicated and uncomplicated; acute pyelonephritis; acute bacterial exacerbation of chronic bronchitis and acute bacterial sinusitis. Levofloxacin, like other fluoroquinolones, inhibits the bacterial DNA gyrase, halting DNA replication. This results in strand breakage on a bacterial chromosome, supercoiling, and resealing. In addition, levofloxacin inhibits a bacterial type II topoisomerase.
CNS Activity
Originator
Approval Year
Cmax
AUC
T1/2
Doses
AEs
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Drug as victim
Tox targets
Sourcing
Sample Use Guides
The usual dose of LEVAQUIN tablets or oral solution is 250 mg, 500 mg, or 750 mg administered orally every 24 hours. The usual dose of LEVAQUIN Injection is 250 mg or 500 mg administered by slow infusion over 60 minutes every 24 hours or 750 mg administered by slow infusion over 90 minutes every 24 hours.
Nosocomial Pneumonia: 750 mg during 7–14 days
Community Acquired Pneumonia: 500 mg during 7–14 days
Community Acquired Pneumonia§ 750 mg during 5 days
Complicated Skin and Skin Structure Infections (SSSI) 750 mg during 7–14 days
Uncomplicated SSSI 500 mg during 7–10 days
Chronic Bacterial Prostatitis 500 mg during 28 days
Complicated Urinary Tract Infection (cUTI) or Acute Pyelonephritis (AP) 750 mg during 5 days
Complicated Urinary Tract Infection (cUTI) or Acute Pyelonephritis (AP) 250 mg during 10 days
Uncomplicated Urinary Tract Infection 250 mg 3 during days
Acute Bacterial Exacerbation of Chronic Bronchitis (ABECB) 500 mg during 7 days
Acute Bacterial Sinusitis (ABS) 750 mg days or 500 mg during 10–14 days.
Route of Administration:
Other
Levofloxacin was compared to ofloxacin and ciprofloxacin against > 6000 recent clinical isolates of Gram-positive and Gram-negative bacteria from six different countries. This international multicenter study demonstrated a high level of antibacterial activity of levofloxacin against all the members of Enterobacteriaceae [minimum inhibitory concentration (MIC)50s, < or = 0.03 to 0.12 mg/L] except Providencia rettgeri (MIC50, 2 mg/L), and Providencia stuartii (MIC50, 1 mg/L). Levofloxacin was also active against non-enteric Gram-negative bacilli, including Acinetobacter species (MIC50s, < or = 0.03 to 1 mg/L), Pseudomonas species (MIC50s, 0.5 to 1 mg/L) and Xanthomonas maltophilia (MIC50, 0.5 mg/L). Overall, levofloxacin inhibited 50% and 90% of all the tested strains at the concentrations of 0.12 and 4 mg/L, respectively. The activity of levofloxacin was generally two-fold greater than ofloxacin and equal to or slightly less potent than ciprofloxacin.