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

• ChemBase编号: 853
• 分子式: C17H19F2N3O3
• 平均质量: 351.3478664
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC传统名: lomefloxacin
• 商标名: Bareon; Maxaquin
• 别名: LFLX; lomefloxacin hydrochloride; Lomefloxacine [French]; Lomefloxacino [Spanish]; Lomefloxacinum [Latin]; Lomefloxacin

登记号

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

理论计算性质

JChem

• Acid pKa: 5.6432548
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): -0.67024356
• LogD (pH = 7.4): -0.392002
• Log P: -0.3897759
• 摩尔折射率: 90.112 cm^3
• 极化性: 32.745754 Å^3
• 极化表面积: 72.88 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.0
• LOG S: -3.52
• 溶解度: 1.06e-01 g/l

分子性质

理化性质

• 溶解度: 27.2 mg/mL
• 疏水性(logP): 2.8

详细说明

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]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com