ALALEVONADIFLOXACIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H26FN3O5
Molecular Weight	431.4573
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H](N)C(=O)OC1CCN(CC1)C2=C(F)C=C3C(=O)C(=CN4[C@@H](C)CCC2=C34)C(O)=O

InChI

InChIKey=OUXXDXXQNWKOIF-RYUDHWBXSA-N

InChI=1S/C22H26FN3O5/c1-11-3-4-14-18-15(20(27)16(21(28)29)10-26(11)18)9-17(23)19(14)25-7-5-13(6-8-25)31-22(30)12(2)24/h9-13H,3-8,24H2,1-2H3,(H,28,29)/t11-,12-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H26FN3O5
Molecular Weight	431.4573
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
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
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	17027349
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	19029326
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:16:45 GMT 2023` Edited by `admin` on `Fri Dec 15 17:16:45 GMT 2023`
Record UNII	57B7E1D1TG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALALEVONADIFLOXACIN

Official Name

English

L-ALANINE, 1-((5S)-2-CARBOXY-9-FLUORO-6,7-DIHYDRO-5-METHYL-1-OXO-1H,5H-BENZO(IJ)QUINOLIZIN-8-YL)-4-PIPERIDINYL ESTER

Systematic Name

English

alalevonadifloxacin [INN]

Common Name

English

Alalevonadifloxacin [WHO-DD]

Common Name

English

L-ALANINE, 1-((5S)-2-CARBOXY-9-FLUORO-6,7-DIHYDRO-5-METHYL-1-OXO-1H,5H-BENZO(IJ)QUINOLIZIN-8-YL)-4-PIPERIDINYL ESTER, (-)-

Systematic Name

English

Code System Code Type Description

INN

10192