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

• ChemBase ID: 853
• Molecular Formular: C17H19F2N3O3
• Molecular Mass: 351.3478664
• Monoisotopic Mass: 351.13944792
• SMILES: Fc1c(N2CC(NCC2)C)c(F)cc2c1n(CC)cc(c2=O)C(=O)O
• Canonical SMILES: CCn1cc(C(=O)O)c(=O)c2c1c(F)c(N1CCNC(C1)C)c(c2)F
• InChI: InChI=1S/C17H19F2N3O3/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)
• InChIKey: ZEKZLJVOYLTDKK-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
• IUPAC Traditional name: lomefloxacin
• Brand Name: Bareon; Maxaquin
• Synonyms: LFLX; lomefloxacin hydrochloride; Lomefloxacine [French]; Lomefloxacino [Spanish]; Lomefloxacinum [Latin]; Lomefloxacin

Database IDs

• CAS Number: 98079-51-7
• PubChem SID: 160964316; 46508499
• PubChem CID: 3948

CALCULATED PROPERTIES

JChem

• 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
• 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

ALOGPS 2.1

• Log P: 0.0
• LOG S: -3.52
• Solubility (Water): 1.06e-01 g/l

PROPERTIES

Physical Property

• Solubility: 27.2 mg/mL
• Hydrophobicity(logP): 2.8

DETAILS

DrugBank - DB00978

• Drug Groups: approved
• Description: Lomefloxacin is a fluoroquinolone antibiotic, used to treat bacterial infections including bronchitis and urinary tract infections. It is also used to prevent urinary tract infections prior to surgery.
• Indication: For the treatment of bacterial infections of the respiratory tract (chronic bronchitis) and urinary tract, and 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.
• Pharmacology: Lomefloxacin is a fluoroquinolone antibiotic used to treat chronic bronchitis, as well as complicated and uncomplicated urinary tract infections. It is also used as a prophylactic or preventative treatment to prevent urinary tract infections in patients undergoing transrectal or transurethral surgical procedures. Flouroquinolones such as lomefloxacin possess excellent activity against gram-negative aerobic bacteria such as E.coli and Neisseria gonorrhoea as well as gram-positive bacteria including S. pneumoniae and Staphylococcus aureus. They also posses effective activity against shigella, salmonella, campylobacter, gonococcal organisms, and multi drug resistant pseudomonas and enterobacter.
• Toxicity: Adverse reactions include peripheral neuropathy, nervousness, agitation, anxiety, and phototoxic events (rash, itching, burning) due to sunlight exposure.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Minimally metabolized although 5 metabolites have been identified in human urine. 65% appears as the parent drug in urine and 9% as the glucuronide metabolite.
• Absorption: Rapid and nearly complete with approximately 95% to 98% of a single oral dose being absorbed.
• Half Life: 8 hours
• Protein Binding: 10%
• Elimination: The urinary excretion of lomefloxacin was virtually complete within 72 hours after cessation of dosing, with approximately 65% of the dose being recovered as parent drug and 9% as its glucuronide metabolite.
• Clearance: * 271 mL/min/1.73 m2 [creatinine clearance of 110 mL/min/1.73 m2]; * 31 mL/min/1.73 m2 [creatinine clearance of 0 mL/min/1.73 m2]
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