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

• ChemBase ID: 70344
• Molecular Formular: C17H20ClF2N3O3
• Molecular Mass: 387.8088064
• Monoisotopic Mass: 387.11612564
• SMILES: n1(cc(c(=O)c2cc(c(c(c12)F)N1CC(NCC1)C)F)C(=O)O)CC.Cl
• Canonical SMILES: CCn1cc(C(=O)O)c(=O)c2c1c(F)c(N1CCNC(C1)C)c(c2)F.Cl
• InChI: InChI=1S/C17H19F2N3O3.ClH/c1-3-21-8-11(17(24)25)16(23)10-6-12(18)15(13(19)14(10)21)22-5-4-20-9(2)7-22;/h6,8-9,20H,3-5,7H2,1-2H3,(H,24,25);1H
• InChIKey: KXEBLAPZMOQCKO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride
• IUPAC Traditional name: lomefloxacin hydrochloride
• Synonyms: Lomefloxacin hydrochloride; Maxaquin; Okacyn; Uniquin; 1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid Hydrochloride; Alkaflox; Bareon; Chimono; Lomebact; Lomef 400; Lomflox; Lomitas; Lomoxin; Mazaquin; NY 198; Orchacin; SC 47111; 1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid; Lomefloxacin hydrochloride

Database IDs

• CAS Number: 98079-52-8
• MDL Number: MFCD00214312
• PubChem SID: 162036064; 24278514
• PubChem CID: 68624

CALCULATED PROPERTIES

• Molar Refractivity: 90.112 cm^3
• Polarizability: 32.745754 Å^3
• Polar Surface Area: 72.88 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 5.6432548
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.67024356
• LogD (pH = 7.4): -0.392002
• Log P: -0.3897759

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 290-300°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: IRRITANT
• RTECS: VB1997500
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: 95+%
• Salt Data: hydrochloride
• Suitability: suitable for 1694 per US EPA

DETAILS

Selleck Chemicals - S2539

Research Area: Infection
Biological Activity:
Lomefloxacin hydrochloride (Maxaquin) is a hydrochloride salt of lomefloxacin and is a fluoroquinolone antibiotic.Lomefloxacin hydrochloride (Maxaquin) is used to treat bacterial infections including bronchitis and urinary tract infections. Lomefloxacin hydrochloride (Maxaquin) is also used to prevent urinary tract infections prior to surgery. [1]

Sigma Aldrich - L2906

Application
Lomefloxacin is a fluoroquinolone antibiotic that is commonly used to treat bacterial infections, including bronchitis and urinary tract infections. It is used as a pre-operative prophylactic to prevent urinary tract infection caused by S. pneumoniae, H. influenzae, S. aureus, P. aeruginosa, E. cloacae, P. mirabilis, C. civersus, S. asprphyticus, E. coli, and K. pneumoniae. It is used to induce genomic instability in mice1 and modification of the kinetics of growth of Gram-negative bacteria2.
Biochem/physiol Actions
Lomefloxacin inhibits bacterial DNA gyrase (topoisomerase II) and topoisomerase IV.
Lomefloxacin is a bactericidal fluoroquinolone agent that is active against gram-negative and gram-positive organisms. Lomefloxacin inhibits bacterial DNA gyrase (topoisomerase II) and topoisomerase IV, which are needed for the transcription and replication of bacterial DNA. DNA gyrase is thought to be the primary quinolone target for gram-negative bacteria. Topoisomerase IV is thought to be the primary target in gram-positive organisms. The inhibition of the topoisomerases results in strand breakage of the bacterial chromosome, supercoiling, and resealing. Therefore, DNA replication and transcription is inhibited .

Toronto Research Chemicals - L469415

Lomefloxacin is a fluorinated quinolone antibacterial. Lomefloxacin is a DNA gyrase antagonist.

REFERENCES

• http://en.wikipedia.org/wiki/Lomefloxacin
• Hirose, T., et al.: Antimicrob. Agents Chemother., 31, 854 (1987)
• Sanzgiri, Y.D.. et al.: Anal. Profiles Drug Subs. Excip. 23, 321 (1994)