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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H21FN2O4
Molecular Weight 360.3794
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Levonadifloxacin

SMILES

C[C@H]1CCC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N4CCC(O)CC4

InChI

InChIKey=JYJTVFIEFKZWCJ-JTQLQIEISA-N
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

HIDE SMILES / InChI

Molecular Formula C19H21FN2O4
Molecular Weight 360.3794
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Levonadifloxacin is the S-(-) isomer of the benzoquinolizine fluoroquinolone nadifloxacin and is two- to four-fold more active than the racemic mixture. Levonadifloxacin is a potent antibacterial agent against Gram-positive bacteria especially against methicillin resistance Staphylococcus aureus. It also possesses potent bactericidal activity against other resistant variants like quinolone-resistant Staphylococcus aureus, vancomycin and glycopeptide intermediate Staphylococcus aureus and vancomycin resistant Staphylococcus aureus. Intravenous dosage form developed to treat complicated skin and skin structure infections and has recently completed Phase III studies in India and Phase I studies in USA.

Approval Year

PubMed

PubMed

TitleDatePubMed
Antibacterial susceptibility of a vancomycin-resistant Staphylococcus aureus strain isolated at the Hershey Medical Center.
2003 Nov
Antianaerobic activity of a novel fluoroquinolone, WCK 771, compared to those of nine other agents.
2004 Aug
Antistaphylococcal activity of WCK 771, a tricyclic fluoroquinolone, in animal infection models.
2004 Dec
In vitro activity of the new quinolone WCK 771 against staphylococci.
2004 Sep
Activity of the new quinolones WCK 771, WCK 1152 and WCK 1153 against clinical isolates of Streptococcus pneumoniae and Streptococcus pyogenes.
2005 Dec
Activity of the new quinolone WCK 771 against pneumococci.
2005 Jan
Recently approved and investigational antibiotics for treatment of severe infections caused by Gram-positive bacteria.
2005 Oct
Validated chiral high-performance liquid chromatography method for a novel anti-methicillin-resistant Staphylococcus aureus fluoroquinolone WCK 771.
2006 Mar 3
The anti-methicillin-resistant Staphylococcus aureus quinolone WCK 771 has potent activity against sequentially selected mutants, has a narrow mutant selection window against quinolone-resistant Staphylococcus aureus, and preferentially targets DNA gyrase.
2006 Nov
Nadifloxacin: a quinolone for topical treatment of skin infections and potential for systemic use of its active isomer, WCK 771.
2006 Oct
Simple liquid chromatography-tandem mass spectrometry method for determination of novel anti-methicillin-resistant Staphylococcus aureus fluoroquinolone WCK 771 in human serum.
2007 Feb 1
In vitro activity of the quinolone WCK 771 against recent U.S. hospital and community-acquired Staphylococcus aureus pathogens with various resistance types.
2009 Feb
Intrapulmonary Pharmacokinetics of Levonadifloxacin following Oral Administration of Alalevonadifloxacin to Healthy Adult Subjects.
2018 Mar
In Vitro Activities of the Benzoquinolizine Fluoroquinolone Levonadifloxacin (WCK 771) and Other Antimicrobial Agents against Mycoplasmas and Ureaplasmas in Humans, Including Isolates with Defined Resistance Mechanisms.
2018 Nov
Electrocardiographic Effects of a Supratherapeutic Dose of WCK 2349, a Benzoquinolizine Fluoroquinolone.
2019 Jan
Identification of metabolites of novel Anti-MRSA fluoroquinolone WCK 771 in mouse, rat, rabbit, dog, monkey and human urine using liquid chromatography tandem mass spectrometry.
2019 Jul
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:05:27 UTC 2023
Edited
by admin
on Fri Dec 15 17:05:27 UTC 2023
Record UNII
8WHH66L098
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Levonadifloxacin
INN  
INN  
Official Name English
Nadifloxacin, (S)-
Common Name English
(5S)-9-Fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidinyl)-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid
Systematic Name English
WCK771 FREE BASE
Code English
Levonadifloxacin [WHO-DD]
Common Name English
1H,5H-Benzo[ij]quinolizine-2-carboxylic acid, 9-fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidinyl)-5-methyl-1-oxo-, (5S)-
Systematic Name English
(5S)-9-fluoro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinolizine-2-carboxylic acid
Systematic Name English
1H,5H-Benzo[ij]quinolizine-2-carboxylic acid, 9-fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidinyl)-5-methyl-1-oxo-, (S)-
Common Name English
(S)-9-Fluoro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid
Systematic Name English
(S)-(-)-Nadifloxacin
Common Name English
WCK-771 FREE BASE
Code English
levonadifloxacin [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C795
Created by admin on Fri Dec 15 17:05:27 UTC 2023 , Edited by admin on Fri Dec 15 17:05:27 UTC 2023
Code System Code Type Description
PUBCHEM
9850038
Created by admin on Fri Dec 15 17:05:27 UTC 2023 , Edited by admin on Fri Dec 15 17:05:27 UTC 2023
PRIMARY
NCI_THESAURUS
C83879
Created by admin on Fri Dec 15 17:05:27 UTC 2023 , Edited by admin on Fri Dec 15 17:05:27 UTC 2023
PRIMARY
FDA UNII
8WHH66L098
Created by admin on Fri Dec 15 17:05:27 UTC 2023 , Edited by admin on Fri Dec 15 17:05:27 UTC 2023
PRIMARY
EPA CompTox
DTXSID70165599
Created by admin on Fri Dec 15 17:05:27 UTC 2023 , Edited by admin on Fri Dec 15 17:05:27 UTC 2023
PRIMARY
SMS_ID
300000034280
Created by admin on Fri Dec 15 17:05:27 UTC 2023 , Edited by admin on Fri Dec 15 17:05:27 UTC 2023
PRIMARY
INN
8649
Created by admin on Fri Dec 15 17:05:27 UTC 2023 , Edited by admin on Fri Dec 15 17:05:27 UTC 2023
PRIMARY
CAS
154357-42-3
Created by admin on Fri Dec 15 17:05:27 UTC 2023 , Edited by admin on Fri Dec 15 17:05:27 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
RACEMATE -> ENANTIOMER
TARGET ORGANISM->INHIBITOR
TARGET ORGANISM->INHIBITOR
TARGET ORGANISM->INHIBITOR
TARGET ORGANISM->INHIBITOR
TARGET ORGANISM->INHIBITOR
TARGET ORGANISM->INHIBITOR
SALT/SOLVATE -> PARENT
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PRODRUG -> METABOLITE ACTIVE
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ACTIVE MOIETY