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Levonadifloxacin

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Levonadifloxacin
Clinical data
Trade namesEmrok
Other names(S)-(-)-Nadifloxacin
Routes of
administration		Parenteral
ATC code
Legal status
Legal status
  • Rx in India
Identifiers
  • (12S)-7-Fluoro-8-(4-hydroxypiperidin-1-yl)-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylic acid
CAS Number
PubChemCID
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC19H21FN2O4
Molar mass360.385 g·mol−1
3D model (JSmol)
  • C[C@H]1CCC2=C3N1C=C(C(=O)C3=CC(=C2N4CCC(CC4)O)F)C(=O)O
  • InChI=InChI=1S/C19H21FN2O4/c1-10-2-3-12-16-13(18(24)14(19(25)26)9-22(10)16)8-15(20)17(12)21-6-4-11(23)5-7-21/h8-11,23H,2-7H2,1H3,(H,25,26)/t10-/m0/s1
  • Key:JYJTVFIEFKZWCJ-JTQLQIEISA-N

Levonadifloxacin (trade nameEmrok) is an antibiotic drug of thefluoroquinolone class.[1][2] Chemically, it is the (S)-enantiomer of theracemic drugnadifloxacin.

It is approved in India for the treatment of skin and soft tissue infections ofGram-positive bacteria.[3] It is also being studied for potential use againstresistant strains of bacteria includingStreptococcus pneumoniae,Streptococcus pyogenes,Haemophilus influenzae, andMoraxella catarrhalis.[4]

Levonadifloxacin has poororal bioavailability. Aprodrug of levonadifloxacin with high oral bioavailability,alalevonadifloxacin, has been developed to mitigate this problem.[5]

References

[edit]
  1. ^Patel A, Sangle GV, Trivedi J, Shengule SA, Thorve D, Patil M, et al. (April 2020)."Levonadifloxacin, a Novel Benzoquinolizine Fluoroquinolone, Modulates Lipopolysaccharide-Induced Inflammatory Responses in Human Whole-Blood Assay and Murine Acute Lung Injury Model".Antimicrobial Agents and Chemotherapy.64 (5).doi:10.1128/aac.00084-20.PMC 7179645.PMID 32152077.
  2. ^Bakthavatchalam YD, Shankar A, Muniyasamy R, Peter JV, Marcus Z, Triplicane Dwarakanathan H, et al. (August 2020). "Levonadifloxacin, a recently approved benzoquinolizine fluoroquinolone, exhibits potent in vitro activity against contemporary Staphylococcus aureus isolates and Bengal Bay clone isolates collected from a large Indian tertiary care hospital".The Journal of Antimicrobial Chemotherapy.75 (8):2156–2159.doi:10.1093/jac/dkaa142.PMID 32361727.
  3. ^"Levonadifloxacin".AdisInsight. Springer Nature Switzerland AG.
  4. ^Bhagwat SS, Nandanwar M, Kansagara A, Patel A, Takalkar S, Chavan R, et al. (2019)."Levonadifloxacin, a Novel Broad-Spectrum Anti-MRSA Benzoquinolizine Quinolone Agent: Review of Current Evidence".Drug Design, Development and Therapy.13:4351–4365.doi:10.2147/DDDT.S229882.PMC 6935279.PMID 31920285.
  5. ^Bhawsar S, Kale R, Deshpande P, Yeole R, Bhagwat S, Patel M (December 2021). "Design and synthesis of an oral prodrug alalevonadifloxacin for the treatment of MRSA infection".Bioorganic & Medicinal Chemistry Letters.54: 128432.doi:10.1016/j.bmcl.2021.128432.PMID 34757217.
Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)
DHFR inhibitor
Sulfonamides
(DHPS inhibitor)
Short-acting
Intermediate-acting
Long-acting
Other/ungrouped
Combinations
Other DHPS inhibitors
Quinolones
(inhibit bacterial
topoisomerase
and/orDNA gyrase,
thereby inhibiting
DNA replication)
1st generation
Fluoroquinolones
2nd generation
3rd generation
4th generation
Veterinary
Newer non-fluorinated
Related (DG)
Anaerobic DNA
inhibitors
Nitroimidazole derivatives
RNA synthesis
Rifamycins/
RNA polymerase
Lipiarmycins
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