Levonadifloxacin

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 Search

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

Description
Sources: https://adisinsight.springer.com/drugs/800016734 | https://www.ncbi.nlm.nih.gov/pubmed/30861568 | https://www.jmilabs.com/data/posters/Microbe16-WCK-771-Sunday-456.pdf

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

Title	Date	PubMed
Antibacterial susceptibility of a vancomycin-resistant Staphylococcus aureus strain isolated at the Hershey Medical Center.	2003 Nov	14563898
Antianaerobic activity of a novel fluoroquinolone, WCK 771, compared to those of nine other agents.	2004 Aug	15273148
Antistaphylococcal activity of WCK 771, a tricyclic fluoroquinolone, in animal infection models.	2004 Dec	15561853
In vitro activity of the new quinolone WCK 771 against staphylococci.	2004 Sep	15328094
Activity of the new quinolones WCK 771, WCK 1152 and WCK 1153 against clinical isolates of Streptococcus pneumoniae and Streptococcus pyogenes.	2005 Dec	16239291
Activity of the new quinolone WCK 771 against pneumococci.	2005 Jan	15649298
Recently approved and investigational antibiotics for treatment of severe infections caused by Gram-positive bacteria.	2005 Oct	16098786
Validated chiral high-performance liquid chromatography method for a novel anti-methicillin-resistant Staphylococcus aureus fluoroquinolone WCK 771.	2006 Mar 3	16426621
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	16940059
Nadifloxacin: a quinolone for topical treatment of skin infections and potential for systemic use of its active isomer, WCK 771.	2006 Oct	17020421
Intrapulmonary Pharmacokinetics of Levonadifloxacin following Oral Administration of Alalevonadifloxacin to Healthy Adult Subjects.	2018 Mar	29263070
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	30104279
Electrocardiographic Effects of a Supratherapeutic Dose of WCK 2349, a Benzoquinolizine Fluoroquinolone.	2019 Jan	30369076
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	30861568

Patents

Name

Type

Language

Levonadifloxacin

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