6-fluoro-1-(4-fluorophenyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride

• ChemBase ID: 122599
• Molecular Formular: C21H20ClF2N3O3
• Molecular Mass: 435.8516064
• Monoisotopic Mass: 435.11612564
• SMILES: c1(c(=O)c2c(n(c1)c1ccc(cc1)F)cc(N1CCN(CC1)C)c(c2)F)C(=O)O.Cl
• Canonical SMILES: CN1CCN(CC1)c1cc2c(cc1F)c(=O)c(cn2c1ccc(cc1)F)C(=O)O.Cl
• InChI: InChI=1S/C21H19F2N3O3.ClH/c1-24-6-8-25(9-7-24)19-11-18-15(10-17(19)23)20(27)16(21(28)29)12-26(18)14-4-2-13(22)3-5-14;/h2-5,10-12H,6-9H2,1H3,(H,28,29);1H
• InChIKey: JFMGBGLSDVIOHL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-fluoro-1-(4-fluorophenyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride
• IUPAC Traditional name: 6-fluoro-1-(4-fluorophenyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride; difloxacin hydrochloride
• Synonyms: 6-Fluoro-1-(4-fluorophenyl)-1,4-dihydro-7-(4-methylpiperazino)-4-oxo-3-quinolinecarboxylic acid hydrochloride; Difloxacin hydrochloride; Difloxacin HCl; 6-Fluoro-1-(4-fluorophenyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid Hydrochloride Salt; Difloxacin Hydrochloride Salt; 6-fluoro-1-(4-fluorophenyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride; 6-氟-1-(4-氟苯基)-7-(4-甲基哌嗪-1-基)-4-氧代喹啉-3-甲酸 盐酸盐; 双氟沙星 盐酸盐

Database IDs

• CAS Number: 98106-17-3; 91296-86-5
• MDL Number: MFCD03840489
• PubChem SID: 24860689; 162216952
• PubChem CID: 56205

CALCULATED PROPERTIES

• Acid pKa: 5.637776
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.218182
• LogD (pH = 7.4): 1.6240574
• Log P: 2.3609521
• Molar Refractivity: 105.1936 cm^3
• Polarizability: 38.571358 Å^3
• Polar Surface Area: 64.09 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: >245°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• RTECS: VB2008975
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: room temp

Pharmacology Properties

• Target: Others
• Mechanism of Action: DNA gyrase inhibitor

Product Information

• Purity: ≥98% (HPLC)
• Grade: VETRANAL™, analytical standard
• Salt Data: HCl
• Application(s): Antibacterial agent
• Empirical Formula (Hill Notation): C21H19F2N3O3 · HCl

DETAILS

Sigma Aldrich - D2819

Biochem/physiol Actions
Difloxacin inhibits bacterial DNA gyrase and the topoisomerase II enzyme, which inhibits DNA replication and transcription
Fluoroquinolone antibacterial compound. Structurally related to norfloxacin.
Pefloxacin is a synthetic fluoroquinolone that functions an antibacterial agent. It is an analog of norfloxacin. Mode of Action: A ds-DNA binding DNA gyrase inhibitor to dysrupt DNA synthesis. Use to study the metabolism of glycosaminoglycans and collagen in organ cultures of articular cartilage. Antimicrobial spectrum: Pefloxacin is highly active against Staphylococcus aureus, E. coli, other enterobacteria, and Pseudomonas aeruginosa.1 Active against gram-positive bacteria and excellent activity against gram-negative bacteria.2
Application
Difloxacin is a fluoroquinolone antibiotic commonly used in veterinary medicine. It is a potential treatment for Chlamydia trachomatis infections1 and chronic Q fever in humans2. It has been used to study how potential supplementation (magnesium) may reduce quinolone-induced damage in the horse and dog models3.

Sigma Aldrich - 33984

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

Toronto Research Chemicals - D445600

A fluoroquinolone antibacterial structurally related to norfloxacin.

REFERENCES

• Stamm, J.M., et al.: Antimicrob. Ag. Chemother., 29, 193 (1986)
• Granneman, G.R., et al.: Antimicrob. Ag. Chemother., 30, 689 (1986)
• Chu, D.T.W. et al., J. Med. Chem., 1985, 28, 1558, (synth, pharmacol)
• Fernandes, P.B. et al., Antimicrob. Agents Chemother., 1986, 29, 201, (pharmacol)
• Granneman, G.R. et al., Antimicrob. Agents Chemother., 1986, 30, 689, (metab)
• Granneman, G.R. et al., J. Chromatogr., 1987, 413, 199, (hplc)
• Shen, L.L. et al., Biochemistry, 1989, 28, 3886, (mech, sar)
• Xiao, W. et al., J. Pharm. Sci., 1989, 78, 585, (activity)
• Burkhardt, J.E. et al., Vet. Pathol., 1990, 27, 162, (tox)
• Burkhardt, J.E. et al., Fundam. Appl. Toxicol., 1993, 20, 257, (tox)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 159