108437-28-1

Basic information

• Product Name: binfloxacin
• Synonyms: 1,4-Diazabicyclo[3.2.2]nonane,3-quinolinecarboxylic acid deriv.; Binfloxacin; CP 73049
• CAS NO: 108437-28-1
• Molecular Formula: C19H22FN3O3
• Molecular Weight: 359.399
• Mol File: 108437-28-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 565.9°Cat760mmHg
• Flash Point: 296°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 1.21E-13mmHg at 25°C
• Refractive Index: 1.66
• CAS DataBase Reference: binfloxacin(CAS DataBase Reference)
• NIST Chemistry Reference: binfloxacin(108437-28-1)
• EPA Substance Registry System: binfloxacin(108437-28-1)

Safety Data

• Hazardous Substances Data: 108437-28-1(Hazardous Substances Data)

Usage

Uses

Antibacterial (veterinary).

InChI:InChI=1/C19H22FN3O3/c1-2-22-11-14(19(25)26)18(24)13-9-15(20)17(10-16(13)22)23-8-7-21-5-3-12(23)4-6-21/h9-12H,2-8H2,1H3,(H,25,26)

Upstream product

• 70032-25-6 6,7-difluoro-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 283-38-5 1,4-diazabicyclo[3.2.2]nonane 

Relevant articles and documents

Synthesis and structure-activity relationships of 7- diazabicycloalkylquinolones, including danofloxacin, a new quinolone antibacterial agent for veterinary medicine

A series of novel 6-fluoro-7-diazabicycloalkylquinolonecarboxylic acids substituted with various C8 (H, F, Cl, N) and N1 (ethyl, cyclopropyl, vinyl, 2-fluoroethyl, 4-fluorophenyl, 2,4-difluorophenyl) substituents, as well as, 9-fluoro-10-diazabicycloalkylpyridobenzoxazinecarboxylic acids, were prepared and evaluated for antibacterial activity against a range of important veterinary pathogenic bacteria. The diazabicycloalkyl side chains investigated at the 7-position (benzoxazine 10-position) include (1S,4S)-5- methyl-2,5-diazabicyclo[2.2.1]heptane (2), (1S,4S)-2,5- diazabicyclo[2.2.1]heptane (3), (1R,4R)-5-methyl-2,5- diazabicyclo[2.2.1]heptane (4), 8-methyl-3,8-diazabicyclo[3.2.1]octane (5), 9-methyl-3,9-diazabicyclo[4.2.1]nonane (6), 1,4-diazabicyclo[3.2.2]nonane (7), 1,4-diazabicyclo[3.3.1]nonane (8), and 9-methyl-3,9- diazabicyclo[3.3.1]nonane (9). Among these side chains, in vitro potency was not highly variable; other properties therefore proved more critical to the selection of possible development candidates. However, the relative potencies observed for several of these compounds in mouse, swine, and cattle infection models correlated well with those seen in vitro. A combination of the N1 cyclopropyl group and the C7 (1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]hept-2- yl appendage conferred the best overall antibacterial, physiochemical, and pharmacodynamic properties. Hence, danofloxacin (Advocin, 2c) (originally CP- 76,136, 1-cyclopropyl-6-fluoro-7-[(1S,4S)-5-methyl-2,5- diazabicyclo[2.2.1]hept-2-yl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid) was selected as a candidate for development as a therapeutic antibacterial agent for veterinary medicine.

Anti-bacterial substituted bridged-diazabicycloalkyl quinolone carboxylic acids

Antibacterial compounds have the formula STR1 wherein R1 is hydrogen, a pharmaceutically acceptable cation, or alkyl; A is CH, CF, CCl or N; Y is alkyl, haloalkyl, cyclopropyl, vinyl, methoxy, N-methylamino, p-fluorophenyl, p-hydroxyphenyl or p