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79660-72-3

79660-72-3 Structure

79660-72-3 Structure
IdentificationMore
[Name]

Fleroxacin
[CAS]

79660-72-3
[Synonyms]

6,8-DIFLUORO-1-(2-FLUOROETHYL)-1,4-DIHYDRO-7-(4-METHYL-1-PIPERAZINYL)-4-OXO-3-QUINOLINECARBOXYLIC ACID
6,8-DIFLUORO-1-(2-FLUOROETHYL)-1,4-DIHYDRO-7-(4-METHYLPIPERAZINO)-4-OXO-3-QUINOLINECARBOXYLIC ACID
AM-833
FLEROXACIN
MEGALOCIN
MEGALONE
QUINODIS
RO-23-6240
3-quinolinecarboxylicacid,1,4-dihydro-6,8-difluoro-1-(2-fluoroethyl)-7-(4-met
hyl-1-piperazinyl)-4-oxo-
ro23-6240/000
6,8-Difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylicacid
AM-833, Ro-23-6240, Megalocin, Megalone, Quinodis, 6,8-Difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid
AM-833, Megalocin, Megalone, 6,8-Difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methylpiperazino)-4-oxo-3-quinolinecarboxylic acid, 6,8-Difluoro-1-(2-fluoroethyl)1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid
6,8-Difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-7-(4-methyl-1-piperazinyl)quinoline-3-carboxylic acid
[EINECS(EC#)]

677-525-2
[Molecular Formula]

C17H18F3N3O3
[MDL Number]

MFCD00864880
[Molecular Weight]

369.34
[MOL File]

79660-72-3.mol
Chemical PropertiesBack Directory
[Appearance]

White Needle-Like Crystals
[Melting point ]

264-266°C
[Boiling point ]

535.3±50.0 °C(Predicted)
[density ]

1.409±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

0.1 M NaOH: soluble10mg/mL
[form ]

solid
[pka]

-0.54±0.20(Predicted)
[color ]

white to off-white
[Usage]

An antibacterial
[Merck ]

4099
[InChI]

InChI=1S/C17H18F3N3O3/c1-21-4-6-22(7-5-21)15-12(19)8-10-14(13(15)20)23(3-2-18)9-11(16(10)24)17(25)26/h8-9H,2-7H2,1H3,(H,25,26)
[InChIKey]

XBJBPGROQZJDOJ-UHFFFAOYSA-N
[SMILES]

N1(CCF)C2=C(C=C(F)C(N3CCN(C)CC3)=C2F)C(=O)C(C(O)=O)=C1
[CAS DataBase Reference]

79660-72-3(CAS DataBase Reference)
Safety DataBack Directory
[WGK Germany ]

2
[RTECS ]

VB1999050
[HS Code ]

29335990
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethanol-->Potassium carbonate-->Acetic anhydride-->Diethyl ethoxymethylenemalonate-->1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl ester-->QUINOLINE-3-CARBOXYLIC ACID-->2,3,4-Trifluorobenzenamine-->1-Methylpiperazine
Hazard InformationBack Directory
[Description]

Fleroxacin is a new, once daily trifluoroquinolone antibacterial structurally related to norfloxacin. Available in both oral and IV formulations, it is reportedly useful in the treatment of gonorrhea, bacterial enteritis, chronic bronchitis and urinary tract infections. Fleroxacin has a longer serum half-life (9-12 hours) than other drugs of this class, such as ciprofloxacin, enoxacin and norfloxacin.
[Chemical Properties]

White Needle-Like Crystals
[Originator]

Kyorin (Japan)
[Uses]

An antibacterial
[Uses]

antibiotic
[Definition]

ChEBI: A fluoroquinolone antibiotic that is 4-oxo-1,4-dihydroquinoline which is substituted at positions 1, 3, 6, 7 and 8 by 2-fluoroethyl, carboxy, fluoro, 4-methylpiperazin-1-yl and fluoro groups, respectively. It is active against many Gram-positive and Gram-n gative bacteria.
[Manufacturing Process]

6,8-Difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4- oxoquinoline-3-carboxylic acid hydrochloride:
A mixed solution of 1-methylpiperazine (0.34 g) and pyridine (3 ml) was added to 6,7,8-trifluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxoquinoline-3- carboxylic acid (0.12 g) and heated to reflux for 6 hours. After the solvent evaporated and cooled, the residue was adjusted to pH 1 with aqueous hydrochloric acid. The cooled mixture was filtered off and the solid recrystallized from water to give 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7- (4-methyl-1-piperazinyl)-4-oxoquinoline-3-carboxylic acid hydrochloride (0.08 g), melting point 269-271°C (decomp.).
[Brand name]

Quinodis
[Therapeutic Function]

Antibacterial
[storage]

4°C, protect from light
Spectrum DetailBack Directory
[Spectrum Detail]

Fleroxacin(79660-72-3)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

79660-72-3(sigmaaldrich)
[TCI AMERICA]

Fleroxacin,>98.0%(T)(79660-72-3)
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