6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 73035
• Molecular Formular: C17H18F3N3O3
• Molecular Mass: 369.3383296
• Monoisotopic Mass: 369.13002611
• SMILES: c1(cn(c2c(c1=O)cc(c(c2F)N1CCN(CC1)C)F)CCF)C(=O)O
• Canonical SMILES: FCCn1cc(C(=O)O)c(=O)c2c1c(F)c(N1CCN(CC1)C)c(c2)F
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: fleroxacin
• Synonyms: 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; RO 23-6240; 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; Megalone; Fleroxacin; Quinodis; Megalocin; Fleroxacin; 6,8-二氟-1-(2-氟乙基)1,4-二氢-7-(4-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸; 6,8-二氟-1-(2-氟乙基)1,4-二氢-7-(4-甲基哌嗪)-4-氧代-3-喹啉羧酸; 多氟哌酸; 多氟沙星; 氟罗沙星

Database IDs

• CAS Number: 79660-72-3
• MDL Number: MFCD00864880
• PubChem SID: 24860631; 162037955
• PubChem CID: 3357

CALCULATED PROPERTIES

• Acid pKa: 5.4414077
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.1178136
• LogD (pH = 7.4): 0.098635465
• Log P: 1.1188914
• Molar Refractivity: 90.8395 cm^3
• Polarizability: 32.576477 Å^3
• Polar Surface Area: 64.09 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: solid; White Solid
• Melting Point: 264-266°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: VB1999050
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C17H18F3N3O3

DETAILS

Selleck Chemicals - S2469

Research Area: Infection
Biological Activity:
Fleroxacin(Quinodis) is a new broad-spectrum fluoroquinolone. In a study, fleroxacin significantly inhibited cell proliferation in a dose- and time-dependent manner at concentrations of 50-800 microg/mL for 12, 24, and 48 hours. The inhibitory effects of fleroxacin combined with 5-FU appeared synergistic using normalized isobologram and combination index analysis. In vivo, no significant changes in bladder tumor frequency were noted between the control and fleroxacin and 5-FU groups. Significant inhibition of tumor frequency was observed only when fleroxacin was administered with 5-FU.Fleroxacin combined with 5-FU inhibited the proliferation of bladder tumor cell lines both in vitro and in vivo. This combination therapy might be applicable in clinical settings. [1]

Sigma Aldrich - F6807

Application
Fleroxacin is a broad-spectrum antimicrobial fluoroquinolone. It is used in pharmacokinetic studies and is used to study the treatment of intra-abdominal abscesses and travellers’ diarrhea1,2,3.
Biochem/physiol Actions
Fleroxacin is a synthetic trifluorinated quinolone with antimicrobial activity against a variety of pathogens, including mycobacteria, mycoplasmas, chlamydiae, and legionellae. It strongly inhibits the DNA-supercoiling activity of DNA gyrase and DNA topoisomerase 2, which results in cell death4.

Sigma Aldrich - 33930

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - F401250

An antibacterial.

REFERENCES

• Nishikawa T et al. Urology. 2009 Dec;74(6):1370-6
• Hirai, K., et al.: Antimicrob. Ag. Chemother., 29, 1059 (1986)
• Weidekamm, E., et al.: Antimicrob. Ag. Chemother., 31, 1909 (1986)
• Boerema, J.B.J., et al.: J. Antimicrob. Chemother., 21, 140 (1988)