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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H21FN2O4.C6H14N4O2.4H2O
Molecular Weight 606.6415
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVONADIFLOXACIN ARGININE TETRAHYDRATE

SMILES

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

InChI

InChIKey=HYZOLQQTFAWQDZ-HSFRFRSPSA-N
InChI=1S/C19H21FN2O4.C6H14N4O2.4H2O/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;7-4(5(11)12)2-1-3-10-6(8)9;;;;/h8-11,23H,2-7H2,1H3,(H,25,26);4H,1-3,7H2,(H,11,12)(H4,8,9,10);4*1H2/t10-;4-;;;;/m00..../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

Molecular Formula C6H14N4O2
Molecular Weight 174.201
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Antianaerobic activity of a novel fluoroquinolone, WCK 771, compared to those of nine other agents.
2004 Aug
In vitro activity of the new quinolone WCK 771 against staphylococci.
2004 Sep
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
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
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 17:15:51 GMT 2023
Edited
by admin
on Fri Dec 15 17:15:51 GMT 2023
Record UNII
O2N9J968D5
Record Status Validated (UNII)
Record Version
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Name Type Language
LEVONADIFLOXACIN ARGININE TETRAHYDRATE
Common Name English
LEVONADIFLOXACIN TETRAHYDRATE ARGININE SALT
Common Name English
WCK 771 TETRAHYDRATE
Code English
L-ARGININE, MONO((5S)-9-FLUORO-6,7-DIHYDRO-8-(4-HYDROXY-1-PIPERIDINYL)-5-METHYL-1-OXO-1H,5H-BENZO(IJ)QUINOLIZINE-2-CARBOXYLATE), TETRAHYDRATE
Common Name English
WCK771 TETRAHYDRATE
Code English
WCK-771 TETRAHYDRATE
Common Name English
L-ARGININE, (5S)-9-FLUORO-6,7-DIHYDRO-8-(4-HYDROXY-1-PIPERIDINYL)-5-METHYL-1-OXO-1H,5H-BENZO(IJ)QUINOLIZINE-2-CARBOXYLATE, HYDRATE (1:1:4)
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID90233784
Created by admin on Fri Dec 15 17:15:52 GMT 2023 , Edited by admin on Fri Dec 15 17:15:52 GMT 2023
PRIMARY
PUBCHEM
11227255
Created by admin on Fri Dec 15 17:15:52 GMT 2023 , Edited by admin on Fri Dec 15 17:15:52 GMT 2023
PRIMARY
FDA UNII
O2N9J968D5
Created by admin on Fri Dec 15 17:15:52 GMT 2023 , Edited by admin on Fri Dec 15 17:15:52 GMT 2023
PRIMARY
CAS
847545-29-3
Created by admin on Fri Dec 15 17:15:52 GMT 2023 , Edited by admin on Fri Dec 15 17:15:52 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY