Levonadifloxacin

Levonadifloxacin (trade name Emrok) is an antibiotic drug of the fluoroquinolone class.^[1][2] Chemically, it is the (S)-enantiomer of the racemic drug nadifloxacin.

Levonadifloxacin

Clinical data
Trade names	Emrok
Other names	(S)-(-)-Nadifloxacin
Routes of administration	Parenteral
ATC code	J01MA24 (WHO)
Legal status
Legal status	Rx in India
Identifiers
IUPAC name (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	154357-42-3
PubChem CID	9850038
UNII	8WHH66L098
ChEBI	CHEBI:37908
ChEMBL	ChEMBL190561
CompTox Dashboard (EPA)	DTXSID70165599
Chemical and physical data
Formula	C19H21FN2O4
Molar mass	360.385 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@H]1CCC2=C3N1C=C(C(=O)C3=CC(=C2N4CCC(CC4)O)F)C(=O)O
InChI 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

It is approved in India for the treatment of skin and soft tissue infections of Gram-positive bacteria.^[3] It is also being studied for potential use against resistant strains of bacteria including Streptococcus pneumoniae, Streptococcus pyogenes, Haemophilus influenzae, and Moraxella catarrhalis.^[4]

Levonadifloxacin has poor oral bioavailability. A prodrug of levonadifloxacin with high oral bioavailability, alalevonadifloxacin, has been developed to mitigate this problem.^[5]

References

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.