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
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
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 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

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