1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase编号: 249
• 分子式: C19H22FN3O3
• 平均质量: 359.3946832
• 单一同位素质量: 359.1645198
• SMILES: Fc1c(N2CC(NCC2)C)cc2n(C3CC3)cc(c(=O)c2c1C)C(=O)O
• Canonical SMILES: CC1NCCN(C1)c1cc2c(c(c1F)C)c(=O)c(cn2C1CC1)C(=O)O
• InChI: InChI=1S/C19H22FN3O3/c1-10-8-22(6-5-21-10)15-7-14-16(11(2)17(15)20)18(24)13(19(25)26)9-23(14)12-3-4-12/h7,9-10,12,21H,3-6,8H2,1-2H3,(H,25,26)
• InChIKey: AIJTTZAVMXIJGM-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC传统名: grepafloxacin hydrochloride
• 商标名: Raxar
• 别名: Grepafloxacin

登记号

• CAS号: 119914-60-2
• PubChem SID: 160963712; 46507253
• PubChem CID: 72474

理论计算性质

JChem

• Acid pKa: 5.876593
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): -0.26560268
• LogD (pH = 7.4): 0.12430624
• Log P: 0.118112005
• 摩尔折射率: 97.3994 cm^3
• 极化性: 35.853886 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: -0.12
• LOG S: -2.76
• 溶解度: 6.32e-01 g/l

分子性质

理化性质

• 疏水性(logP): 2.9

详细说明

DrugBank - DB00365

• Drug Groups: approved; withdrawn
• Description: Grepafloxacin hydrochloride (Raxar®, Glaxo Wellcome) is an oral broad-spectrum quinoline antibacterial agent used to treat bacterial infections. Grepafloxacin was withdrawn in the United States due to its side effect of lengthening the QT interval on the electrocardiogram, leading to cardiac events and sudden death. [Wikipedia]
• Indication: For treatment of adults with mild to moderate infections caused by susceptible strains of Haemophilus influenzae, Streptococcus pneumoniae, or Moraxella catarrhalis.
• Pharmacology: Grepafloxacin has in vitro activity against a wide range of gram-positive and gram-negative aerobic microorganisms, as well as some atypical microorganisms.
• Toxicity: Withdrawn from the US market in 1999 due to associations with QTc prolongation and adverse cardiovascular events.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Primarily hepatic via CYP1A2 and CYP3A4. The major metabolite is a glucuronide conjugate; minor metabolites include sulfate conjugates and oxidative metabolites. The oxidative metabolites are formed mainly by the cytochrome P450 enzyme CYP1A2, while the cytochrome P450 enzyme CYP3A4 plays a minor role. The nonconjugated metabolites have little antimicrobial activity compared with the parent drug, and the conjugated metabolites have no antimicrobial activity
• Absorption: Rapidly and extensively absorbed following oral administration. The absolute bioavailability is approximately 70%.
• Half Life: 15 ± 3 hours
• Protein Binding: 50%
• External Links: Wikipedia; RxList; Drugs.com