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Details

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
Structure of LEVOFLOXACIN ANHYDROUS

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

HIDE SMILES / InChI

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

Description

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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
LEVAQUIN
Curative
LEVAQUIN
Curative
LEVAQUIN
Curative
LEVAQUIN
Curative
LEVAQUIN
Curative
LEVAQUIN

Cmax

ValueDoseCo-administeredAnalytePopulation
7.9 mg/L
500 mg 2 times / day multiple, intravenous
LEVOFLOXACIN unknown
Homo sapiens
7.8 mg/L
500 mg 2 times / day multiple, oral
LEVOFLOXACIN unknown
Homo sapiens
11.8 mg/L
1000 mg 1 times / day multiple, oral
LEVOFLOXACIN unknown
Homo sapiens
8.85 mg/L
1000 mg single, oral
LEVOFLOXACIN unknown
Homo sapiens
2.04 mg/L
200 mg single, oral
LEVOFLOXACIN unknown
Homo sapiens
6.3 mg/L
500 mg single, intravenous
LEVOFLOXACIN unknown
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
49.6 mg × h/L
500 mg 2 times / day multiple, intravenous
LEVOFLOXACIN unknown
Homo sapiens
59 mg × h/L
500 mg 2 times / day multiple, oral
LEVOFLOXACIN unknown
Homo sapiens
118 mg × h/L
1000 mg 1 times / day multiple, oral
LEVOFLOXACIN unknown
Homo sapiens
111 mg × h/L
1000 mg single, oral
LEVOFLOXACIN unknown
Homo sapiens
19.88 mg × h/L
200 mg single, oral
LEVOFLOXACIN unknown
Homo sapiens
55.3 mg × h/L
500 mg single, intravenous
LEVOFLOXACIN unknown
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7.6 h
500 mg 2 times / day multiple, intravenous
LEVOFLOXACIN unknown
Homo sapiens
8.4 h
500 mg 2 times / day multiple, oral
LEVOFLOXACIN unknown
Homo sapiens
8.9 h
1000 mg 1 times / day multiple, oral
LEVOFLOXACIN unknown
Homo sapiens
7.9 h
1000 mg single, oral
LEVOFLOXACIN unknown
Homo sapiens
5.97 h
200 mg single, oral
LEVOFLOXACIN unknown
Homo sapiens
6.6 h
500 mg single, intravenous
LEVOFLOXACIN unknown
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Substance Class Chemical
Record UNII
RIX4E89Y14
Record Status Validated (UNII)
Record Version