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Levofloxacin
"Descrizione"
by Al222 (18962 pt)
2023-Sep-11 10:02

Review Consensus: 10 Rating: 10 Number of users: 1
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Levofloxacin is a chemical compound, fluoroquinolone (belongs to the third generation of tricyclic quinolones), an antibacterial and antimicrobial antibiotic, with broad-spectrum bactericidal activity against most Gram-negative bacteria (e.g. Escherichia coli ATCC 25922, Proteus hauseri ATCC 15442), many Gram-positive bacteria (e.g. Staphylococcus aureus ATCC 6538) and some anaerobes.

Take only under medical supervision

It comes in the form of a fine powder with coloration ranging from white to yellow-orange.

It was approved by the U.S. FDA in the late 1990s and is used to treat infections primarily located in:

  • lungs
  • urinary tract
  • prostate
  • skin, muscles
  • facial sinuses

The scientific literature attributes to the fluoroquinolones levofloxacin and moxifloxacin, the role of first defenders in the management of pneumonia (1).  

Recently, this study proposed fluoroquinolones due to their immunomodulatory properties, favorable pharmacokinetics, and excellent safety profile as adjuvants in the treatment of patients presenting with COVID-19 (2).

Antibacterial prophylaxis, designed to reduce bacterial infections in more than 40% of pediatric patients with acute myeloid leukemia, has turned toward levofloxacin for its effects in reducing the incidence of febrile neutropenia and bacterial infections (3).

This study evaluated the safety and efficacy of levofloxacin as bacterial prophylaxis in pediatric and young adult patients undergoing allogeneic or autologous hematopoietic stem cell transplantation at a single pediatric center. The findings of the study confirm the validity of levofloxacin prophylaxis significantly associated with a decrease in bloodstream bacterial infection and was not associated with an increased risk of Clostridioides difficile infection rates, increased incidence of acute graft-versus-host disease, and incidence of multidrug-resistant organisms (4).

Today, third- (levofloxacin) and fourth-generation fluoroquinolones (moxifloxacin and gatifloxacin) represent the most viable antibacterial agents for topical use in ophthalmology even though they involve poor bioavailability because of the rapid precorneal elimination of the toxin. Sulfobutyl-ether-β-cyclodextrin is a suitable polyanion to produce polymeric chitosan nanospheres with good properties for ocular administration of levofloxacin (5).

Like all drugs it can cause side effects. Always ask the physician.

Levofloxacin studies

Typical optimal characteristics of the commercial powder product levofloxacin

AppearancePowder white to pale yellow/orange
Melting point-Melting range18-227 °C (424-441 °F)
Boiling point-Boiling range572 °C (1062 °F)
Flash point> 110 °C (> 230 °F)
Purity(HPLC)min. 98.0 area%
Purity(Nonaqueous Titration)min. 96.0 %
Specific rotation [a]20/D-63.0 to -70.0 deg(C=5, CHCl3)
Specific Rotation-66° (C=5,CHCl3)



Where to buy Levofloxacin powder

Levofloxacin 98.0-102.0 HPLC anhydrous 100986-85-4 (sigmaaldrich.com)
100986-85-4_Search_ACCELPHARMTECH
https://www.tcichemicals.com/
Levofloxacin ((-)-Ofloxacin) | Bacterial Inhibitor | MedChemExpress
  • Molecular Formula: C18H20FN3O4
  • Molecular Weight: 361.37 g/mol
  • CAS: 100986-85-4
  • UNII RIX4E89Y14
  • EC Number: 
  • DSSTox Substance ID: DTXSID0041060
  • MDL number  MFCD00865049
  • PubChem Substance ID 329756033    57648297
  • Beilstein  7327015
  • InChl  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
  • InChI Key      GSDSWSVVBLHKDQ-JTQLQIEISA-N
  • SMILES    CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O
  • IUPAC (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
  • ChEBI    63598
  • NSC   758709
  • NACRES  NA.85

Synonyms

  • (3S)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino [2,3,4-ij]quinoline-6-carboxylic acid)
  • Levaquin
  • Ofloxacin, (S)-Isomer
  • (−)-Ofloxacin

References__________________________________________________________________

(1) Metlay JP, Waterer GW, Long AC, Anzueto A, Brozek J, Crothers K, Cooley LA, Dean NC, Fine MJ, Flanders SA, Griffin MR, Metersky ML, Musher DM, Restrepo MI, Whitney CG. Diagnosis and Treatment of Adults with Community-acquired Pneumonia. An Official Clinical Practice Guideline of the American Thoracic Society and Infectious Diseases Society of America. Am J Respir Crit Care Med. 2019 Oct 1;200(7):e45-e67. doi: 10.1164/rccm.201908-1581ST.

(2) Karampela I, Dalamaga M. Could Respiratory Fluoroquinolones, Levofloxacin and Moxifloxacin, Prove to be Beneficial as an Adjunct Treatment in COVID-19? Arch Med Res. 2020 Oct;51(7):741-742. doi: 10.1016/j.arcmed.2020.06.004. 

(3) McCormick M, Friehling E, Kalpatthi R, Siripong N, Smith K. Cost-effectiveness of levofloxacin prophylaxis against bacterial infection in pediatric patients with acute myeloid leukemia. Pediatr Blood Cancer. 2020 Oct;67(10):e28469. doi: 10.1002/pbc.28469.

(4) Gardner JC, Courter JD, Dandoy CE, Davies SM, Teusink-Cross A. Safety and efficacy of prophylactic levofloxacin in pediatric and adult hematopoietic stem cell transplant patients. Transplant Cell Ther. 2021 Dec 4:S2666-6367(21)01404-4. doi: 10.1016/j.jtct.2021.11.017. 

(5) De Gaetano F, Marino A, Marchetta A, Bongiorno C, Zagami R, Cristiano MC, Paolino D, Pistarà V, Ventura CA. Development of Chitosan/Cyclodextrin Nanospheres for Levofloxacin Ocular Delivery. Pharmaceutics. 2021 Aug 19;13(8):1293. doi: 10.3390/pharmaceutics13081293.

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