1.0 2009-07-03 22:03:17 UTC 2026-05-14 16:58:08 UTC T3D2478 Levofloxacin SmallMolecule Levofloxacin is an exogenous organic compound with the formula C18H20FN3O4 and an average molecular weight of 361.37 g/mol. It exists as a solid at room temperature. Levofloxacin belongs to the quinoline carboxylic acids, a subclass of quinolines and derivatives within the organic compounds. It is classified as a drug (PMC4201908) and an antibacterial drug (PMC4201908) used in the treatment of osteomyelitis (PMC9668588) and pneumonia (PMC11721932, PMC1492602). Mechanistically, levofloxacin acts as a DNA synthesis inhibitor (PMC4201908) and a topoisomerase IV inhibitor (PMC4201908). It inhibits bacterial type II topoisomerases, specifically topoisomerase IV and DNA gyrase. By inhibiting the A subunits of DNA gyrase, which are encoded by the gyrA gene, the compound causes supercoiling, resealing, and strand breakage on the bacterial chromosome, thereby inhibiting DNA transcription and replication. Its recorded protein targets include DNA gyrase subunit A (gyrA), DNA topoisomerase 4 subunit A (parC), DNA topoisomerase 2-alpha (TOP2A), the multidrug and toxin extrusion protein 1 (SLC47A1), and the voltage-gated inwardly rectifying potassium channel KCNH2. Levofloxacin has been detected in the prostate. Exposure routes include oral, intravenous, respiratory, inhalation, topical, and ophthalmic. The compound is found in 26 recorded sources, including healthcare, pharmaceuticals and veterinary products (such as quinolone antibacterials, antiinfectives, and drugs for the treatment of tuberculosis), food and food processing (including the processing of meats, fish, or the preparation of sparkling wine or wine), household cleaning and consumer products (such as tobacco pipes and non electric simulated smoking devices), electrical and electronic equipment (including antennas, amplifiers, and discharge lamps), and building and construction floors. Drug Food Toxin Synthetic Toxin Organic Compound Amine Organofluoride Ether Amide Ester Drug Food Toxin Anti-Infective Agent, Urinary Nucleic Acid Synthesis Inhibitor Quinolone Anti-Bacterial Agent Metabolite Synthetic Compound Human Neurotoxin (-)-Ofloxacin (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 (S)-(-)-9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzooxazine-6-carboxylic acid (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 (S)-Ofloxacin Cravit Elequine Floxel Floxin Iquix L-ofloxacin Leroxacin Levaquin Levofloxacin hydrate Levofloxacine Levofloxacino Levofloxacinum Levokacin Levox Levoxacin Mosardal Nofaxin Ofloxacin Ofloxacin S-(-)-form Quixin Reskuin Tavanic C18H20FN3O4 361.3675 361.143784348 (2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid (2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid 100986-85-4 C[C@H]1COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N1CCN(C)CC1 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 GSDSWSVVBLHKDQ-JTQLQIEISA-N Organic compounds Organoheterocyclic compounds Quinolines and derivatives Quinoline carboxylic acids Quinoline carboxylic acids Alkyl aryl ethers Amino acids Aminoquinolines and derivatives Aryl fluorides Azacyclic compounds Benzenoids Benzoxazines Carboxylic acids Dialkylarylamines Fluoroquinolones Haloquinolines Heteroaromatic compounds Hydrocarbon derivatives Hydroquinolines Hydroquinolones Monocarboxylic acids and derivatives N-arylpiperazines N-methylpiperazines Organic oxides Organofluorides Organopnictogen compounds Oxacyclic compounds Pyridinecarboxylic acids Trialkylamines Vinylogous amides 1,4-diazinane Alkyl aryl ether Amine Amino acid Amino acid or derivatives Aminoquinoline Aromatic heteropolycyclic compound Aryl fluoride Aryl halide Azacycle Benzenoid Benzoxazine Carboxylic acid Carboxylic acid derivative Dialkylarylamine Dihydroquinoline Dihydroquinolone Ether Fluoroquinolone Haloquinoline Heteroaromatic compound Hydrocarbon derivative Monocarboxylic acid or derivatives N-alkylpiperazine N-arylpiperazine N-methylpiperazine Organic nitrogen compound Organic oxide Organic oxygen compound Organofluoride Organohalogen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Piperazine Pyridine Pyridine carboxylic acid Pyridine carboxylic acid or derivatives Quinoline-3-carboxylic acid Tertiary aliphatic amine Tertiary aliphatic/aromatic amine Tertiary amine Vinylogous amide Aromatic heteropolycyclic compounds fluoroquinolone antibiotic ofloxacin quinolone antibiotic Detected and Not Quantified Exogenous Cytoplasm Extracellular Prostate Levofloxacin Drug Metabolism Action Pathway SMP0143557 Solid Clear yellow to clear greenish-yellow liquid (L1017). solubility Insoluble logp 2.1 logp -0.02 ALOGPS logs -2.40 ALOGPS solubility 1.44e+00 g/l ALOGPS logp 0.65 ChemAxon pka_strongest_acidic 5.45 ChemAxon pka_strongest_basic 6.2 ChemAxon iupac (2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid ChemAxon average_mass 361.3675 ChemAxon mono_mass 361.143784348 ChemAxon smiles C[C@H]1COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N1CCN(C)CC1 ChemAxon formula C18H20FN3O4 ChemAxon inchi 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 ChemAxon inchikey GSDSWSVVBLHKDQ-JTQLQIEISA-N ChemAxon polar_surface_area 73.32 ChemAxon refractivity 94.94 ChemAxon polarizability 36.69 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 7 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Ingestion; injection; skin contact (L1017). Absorption of ofloxacin after single or multiple doses of 200 to 400 mg is predictable, and the amount of drug absorbed increases proportionately with the dose. Levofloxacin inhibits bacterial type II topoisomerases, topoisomerase IV and DNA gyrase. Levofloxacin, like other fluoroquinolones, inhibits the A subunits of DNA gyrase, two subunits encoded by the gyrA gene. This results in strand breakage on a bacterial chromosome, supercoiling, and resealing; DNA replication and transcription is inhibited. Mainly excreted as unchanged drug (87%); undergoes limited metabolism in humans. Levofloxacin is rapidly and essentially completely absorbed after oral administration. It is distributed into body tissues, especially in the skin and lung tissues. Levofloxacin is stereochemically stable in plasma and urine and does not invert metabolically to its enantiomer, D-ofloxacin. Levofloxacin undergoes limited metabolism in humans and is primarily excreted as unchanged drug in the urine. Following oral administration, approximately 87% of an administered dose was recovered as unchanged drug in urine within 48 hours, whereas less than 4% of the dose was recovered in feces in 72 hours. Less than 5% of an administered dose was recovered in the urine as the desmethyl and N-oxide metabolites, the only metabolites identified in humans. These metabolites have little relevant pharmacological activity. Levofloxacin is excreted largely as unchanged drug in the urine (L1009). Route of Elimination: Mainly excreted as unchanged drug in the urine. Half Life: 6-8 hours LD50: 640 mg/kg (Oral, Rat) No indication of carcinogenicity to humans (not listed by IARC). For the treatment of bacterial conjunctivitis caused by susceptible strains of the following organisms: Corynebacterium species, Staphylococus aureus, Staphylococcus epidermidis, Streptococcus pneumoniae, Streptococcus (Groups C/F/G), Viridans group streptococci, Acinetobacter lwoffii, Haemophilus influenzae, Serratia marcescens. Levofloxacin is a synthetic chemotherapeutic agent used to treat severe and life threatening bacterial infection (L1009). #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bf3126d68> Side effects include disorientation, dizziness, drowsiness, hot and cold flashes, nausea, slurring of speech, swelling and numbness in the face. In the event of an acute overdosage, the stomach should be emptied. The patient should be observed and appropriate hydration maintained. Levofloxacin is not efficiently removed by hemodialysis or peritoneal dialysis. (L1009) DB01137 HMDB01929 149096 CHEMBL33 131410 C07660 63598 Levofloxacin LFX Levofloxacin 18048412 11249554 11975700 14581720 19212411 Wikipedia. Levofloxacin. Last Updated 7 August 2009.: http://en.wikipedia.org/wiki/Levofloxacin RxList: The Internet Drug Index (2009).: http://www.rxlist.com/levaquin-drug.htm Pharmevo (2009). Spectrix. : http://pharmevo.biz/spectrix-detail.html Drugs.com: http://www.drugs.com/cons/Levofloxacin.html BE0000090 IC50 912.01084 uM BindingDB 50366826 IC50 912.011 uM BindingDB 50366826 BE0000742 Levofloxacin inhibits bacterial type II topoisomerases, topoisomerase IV and DNA gyrase. Levofloxacin, like other fluoroquinolones, inhibits the A subunits of DNA gyrase, two subunits encoded by the gyrA gene. This results in strand breakage on a bacterial chromosome, supercoiling, and resealing; DNA replication and transcription is inhibited. BE0003657 IC50 17.9 uM BindingDB 50366826 BE0000366 BE0000429 BE0008385 BE0002388