154357-42-3

Basic information

• Product Name: (S)-(-)-Nadifloxacin
• Synonyms: (S)-(-)-Nadifloxacin;1H,5H-Benzo[ij]quinolizine-2-carboxylic acid, 9-fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidinyl)-5-methyl-1-oxo-, (5S)- (9CI);1H,5H-Benzo[ij]quinolizine-2-carboxylic acid, 9-fluoro-6,7-dihydro-8-(4-hydroxy-1-piperidinyl)-5-methyl-1-oxo-, (S)-;LEVONADIFLOXACIN;(4S)-1-Oxo-4β-methyl-5,6-dihydro-7-(4-hydroxypiperidino)-8-fluoro-4H-3a-aza-1H-phenalene-2-carboxylic acid;(5S)-9-Fluoro-6,7-dihydro-8-(4-hydroxypiperidino)-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid;(S)-(-)-OPC-7251;(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
• CAS NO: 154357-42-3
• Molecular Formula: C19H21FN2O4
• Molecular Weight: 360.383
• Mol File: 154357-42-3.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.46
• CAS DataBase Reference: (S)-(-)-Nadifloxacin(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-Nadifloxacin(154357-42-3)
• EPA Substance Registry System: (S)-(-)-Nadifloxacin(154357-42-3)

Safety Data

• Hazardous Substances Data: 154357-42-3(Hazardous Substances Data)

Usage

Uses

(S)-(-)-Nadifloxacin is an anti-bacterial agent against multidrug-resistant Staphylococcus aureus. Also, it is derived from 6-Fluoro-2-methylquinoline (F595900), which is an quinoline derivative, a highly potent thrombin receptor antagonist.

Upstream product

• 5382-16-1 4-HYDROXYPIPERIDINE 
• 124858-35-1 nadifloxacin 
• 118665-09-1 (S)-5-Bromo-6-fluoro-2-methyl-1,2,3,4-tetrahydro-quinoline 
• 79085-71-5 5-bromo-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline 

Downstream Products

• 948895-92-9 (2'S,5S)-9-fluoro-6,7-dihydro-8-(4-(N-tert-butoxycarbonyl-L-alaninyl-oxy)-piperidin-1-yl)-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid 

Relevant articles and documents

Structure-retention relationship for enantioseparation of selected fluoroquinolones

Fluoroquinolones are popular class of antibiotics with distinct chemical functionality. Most of them are ampholytes with one chiral center. Stereogeneic center is located either in the side ring of Gatifloxacin (GFLX) or in the quinolone core of Ofloxacin (OFLX). These two amphoteric fluoroquinolones have terminal amino groups in common. The unusual Nadifloxacin (NFLX) is an acidic fluoroquinolone with a core chiral center. Owing to chirality and functionality differences among GFLX, OFLX, and NFLX, we mapped these enantiomers onto structure-retention relationship. Amount of acetic acid modifier was studied in screened mobile phase and cellulose tris(3-chloro-4-methyl phenyl carbamate) (Lux cellulose-2) stationary phase. Experimental design of acetic acid% along with column temperature have been applied. Resolution and enantioselectivity have been related to structural features of the studied enantiomers. High amount of acid (0.4%) was optimum for the separation of either side chirality with a proximate amino group (GFLX) or core chirality without basic functionality (NFLX), while low amount (0.2%) is optimum for core chiral center with distal amino group (OFLX). Temperature has no significant effect on resolution and retention of enantiomers except for OFLX. Enantio-retention explains possible chiral selective and nonselective interactions. The proposed methods have been validated for pharmaceutical analyses.