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

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

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
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
Electrocardiographic Effects of a Supratherapeutic Dose of WCK 2349, a Benzoquinolizine Fluoroquinolone.	2019 Jan	30369076

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:05:27 GMT 2023` Edited by `admin` on `Fri Dec 15 17:05:27 GMT 2023`
Record UNII	8WHH66L098
Record Status	`Validated (UNII)`
Record Version

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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