2519 Levofloxacin Levofloxacin is a synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication. Levofloxacin is marketed by Ortho-McNeil under the trade name Levaquin. Chemically, levofloxacin is the S-enantiomer (L-isomer) of ofloxacin. 100986-85-4 149096 C18H20FN3O4 361.143780 Clear yellow to clear greenish-yellow liquid (L1017). Insoluble 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: <i>Corynebacterium</i> species, <i>Staphylococus aureus</i>, <i>Staphylococcus epidermidis</i>, <i>Streptococcus pneumoniae</i>, <i>Streptococcus</i> (Groups C/F/G), Viridans group streptococci, <i>Acinetobacter lwoffii</i>, <i>Haemophilus influenzae</i>, <i>Serratia marcescens</i>. Levofloxacin is a synthetic chemotherapeutic agent used to treat severe and life threatening bacterial infection (L1009). Irreversible peripheral neuropathy, central nervous system toxicity, cardiovascular toxicity, tendon / articular toxicity, and hepatic toxicity. Toxic epidermal necrolysis, coagulation abnormalities and pancytopenia are other possible adverse effect of levofloxacin. Administration of commercial levofloxin (Levaquin), increased risk of tendinitis and tendon rupture in all ages. This adverse reaction most frequently involves the Achilles tendon (L1009, L1017). 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) 2009-07-03T22:03:17Z 2014-12-24T20:25:34Z Cytochrome P450 1A2 (CYP1A2) (A308) Levofloxacin C07660 63598 Levofloxacin DB01137 LFX true Cytochrome P450 1A2 (P05177) (A308) [H][C@]1(C)COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N1CCN(C)CC1 C18H20FN3O4 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 InChIKey=GSDSWSVVBLHKDQ-JTQLQIEISA-N 361.3675 361.143784348 Exogenous Solid 2.1 HMDB01929 CHEMBL33 131410 <p>Valerie Niddam-Hildesheim, &#8220;Preparation of levofloxacin and forms thereof.&#8221; U.S. Patent US20030130507, issued July 10, 2003.</p>