File:Levofloxacin_chemical_structure.svg · Wikimedia Commons · See Wikimedia Commons
levofloxacin
Sign in to saveAlso known as Floxacin, Levaquin, RWJ-25213, DR-3355, Iquix, (-)-Ofloxacin, Ofloxacin S-(-)-form, (3S)-(-)-9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid
Levofloxacin, sold under the brand name Levaquin among others, is a broad-spectrum antibiotic of the fluoroquinolone drug class. It is the left-handed isomer of the medication ofloxacin. It is used to treat a number of bacterial infections including acute bacterial sinusitis, pneumonia, H. pylori (in combination with other medications), urinary tract infections, Legionnaires' disease, chronic bacterial prostatitis, and some types of gastroenteritis. Along with other antibiotics it may be used to treat tuberculosis, meningitis, or pelvic inflammatory disease. It is available by mouth, intraveno
In the Vinony graph
Vinony's link graph records 292 inbound references to levofloxacin, and connects out to sulfamethazine, picrotoxin and tetrahydrodeoxycorticosterone.
It is catalogued under topics including 1,4-di-hydro-7-(1-piperazinyl)-4-oxo-3-quinolinecarboxylic acids, 4-Methylpiperazin-1-yl compounds and Drugboxes which contain changes to verified fields.
Vinony links it to 38 Wikipedia language editions.
Key facts
- Drug.StdInChI
- 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
- Drug.StdInChIKey
- GSDSWSVVBLHKDQ-JTQLQIEISA-N
- Drug.density
- 1.5±0.1
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 462090938
- Drug.image
- Levofloxacin skeletal formula from xtal 2019.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250
- Drug.alt
- Skeletal formula of a levofloxacin molecule
- Drug.image2
- Levofloxacin_ball-and-stick_model_from_xtal_2019.png
- Drug.image_class2
- bg-transparent
- Drug.alt2
- Ball-and-stick model of a levofloxacin molecule
- Drug.tradename
- Levaquin, others
- Drug.MedlinePlus
- a697040
- Drug.DailyMedID
- Levofloxacin
- Drug.routes_of_administration
- By mouth, intravenous (IV), eye drops
- Drug.class
- Fluoroquinolone
via Wikipedia infobox
Chemical data
- Formula
- C18H20FN3O4
- Molecular weight
- 361.4 g/mol
- IUPAC name
- (2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
- SMILES
- C[C@H]1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O
- InChIKey
- GSDSWSVVBLHKDQ-JTQLQIEISA-N
- XLogP
- -0.4
- Polar surface area
- 73.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Research
12,754 papers- Levofloxacin.Expert opinion on pharmacotherapy · 1999
- Levofloxacin in veterinary medicine: a literature review.Research in veterinary science · 2021
- Levofloxacin for the treatment of pyelonephritis.Expert opinion on pharmacotherapy · 2013
- Levofloxacin-based therapy as an efficient alternative for eradicating Helicobacter pylori infection in Iran: a systematic review and meta-analysis.Journal of global antimicrobial resistance · 2022
- Levofloxacin in the treatment of community-acquired pneumonia.Expert review of anti-infective therapy · 2010
via PubMed
Wikidata facts
- Mass
- 361.144
Show 6 more facts
- Commons category
- Levofloxacin
- chemical formula
- C₁₈H₂₀FN₃O₄
- canonical SMILES
- CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O
- isomeric SMILES
- C[C@H]1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O
- World Health Organisation international non-proprietary name
- levofloxacin
- stylized name
- levoFLOXacin
Sources (8)
via Wikidata · CC0
~22 min read
Encyclopedic overview
20 sectionsContents
- Medical uses
- Pregnancy and breastfeeding
- Children
- Spectrum of activity
- Resistance
- Contraindications and interactions
- Adverse effects
- Overdose
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Economics
- Availability
- Usage
- Litigation
- Brand names
- References
Levofloxacin, sold under the brand name Levaquin among others, is a broad-spectrum antibiotic of the fluoroquinolone drug class. It is the left-handed isomer of the medication ofloxacin. It is used to treat a number of bacterial infections including acute bacterial sinusitis, pneumonia, H. pylori (in combination with other medications), urinary tract infections, Legionnaires' disease, chronic bacterial prostatitis, and some types of gastroenteritis. Along with other antibiotics it may be used to treat tuberculosis, meningitis, or pelvic inflammatory disease. It is available by mouth, intravenously, and in eye drop form.
Common side effects include nausea, diarrhea, and trouble sleeping. A warning concerning all fluoroquinolones was issued in 2016: "An FDA safety review has shown that fluoroquinolones when used systemically (i.e. tablets, capsules, and injectable) are associated with disabling and potentially permanent serious adverse effects that can occur together. These adverse effects can involve the tendons, muscles, joints, nerves, and central nervous system."
Excerpted from Wikipedia’s “levofloxacin” article, available under the CC BY-SA 4.0 licence.