1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase编号: 916
• 分子式: C19H22FN3O4
• 平均质量: 375.3940832
• 单一同位素质量: 375.15943442
• SMILES: Fc1c(N2CC(NCC2)C)c(OC)c2n(C3CC3)cc(c(=O)c2c1)C(=O)O
• Canonical SMILES: COc1c(N2CCNC(C2)C)c(F)cc2c1n(cc(c2=O)C(=O)O)C1CC1
• InChI: InChI=1S/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26)
• InChIKey: XUBOMFCQGDBHNK-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC传统名: gatifloxacin; 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 商标名: Tequin; Zymar
• 别名: 1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid; Tequin; Zymar; gatifloxacin; Gatifloxacin; Gatiflo; Tequin and Zymar; 1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; Gatifloxacin

登记号

• CAS号: 112811-59-3; 160738-57-8
• MDL号: MFCD00895399
• PubChem SID: 160964379; 46506159
• PubChem CID: 5379

理论计算性质

JChem

• Acid pKa: 5.685334
• 质子受体: 7
• 质子供体: 2
• LogD (pH = 5.5): -0.87816894
• LogD (pH = 7.4): -0.580783
• Log P: -0.58031964
• 摩尔折射率: 98.8214 cm^3
• 极化性: 36.64735 Å^3
• 极化表面积: 82.11 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.23
• LOG S: -2.77
• 溶解度: 6.31e-01 g/l

分子性质

理化性质

• 溶解度: 60 mg/mL (at pH 4); Chloroform; H2O; Methanol (Sparingly)
• 外观: Off-White Solid
• 熔点: 185-187°C (dec.)
• 疏水性(logP): 2.6

安全信息

• 保存条件: -20°C; -20°C Freezer

药理学性质

• 生物活性机理: Inhibits the bacterial enzymes DNA gyrase and topoisomerase IV

产品相关信息

• 成盐信息: Free Base
• 应用领域: Antibacterial; Antibiotic

详细说明

DrugBank - DB01044

• Drug Groups: approved; investigational
• Description: Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial enzymes DNA gyrase and topoisomerase IV. Bristol-Myers Squibb introduced Gatifloxacin in 1999 under the proprietary name Tequin? for the treatment of respiratory tract infections, having licensed the medication from Kyorin Pharmaceutical Company of Japan. Allergan produces an eye-drop formulation called Zymar?. Gatifloxacin is available as tablets and in various aqueous solutions for intravenous therapy. [Wikipedia]
• Indication: For the treatment of bronchitis, sinusitis, community-acquired pneumonia, and skin infections (abscesses, wounds) caused by S. pneumoniae, H. influenzae, S. aureus, M. pneumoniae, C. pneumoniae, L. pneumophila, S. pyogenes
• Pharmacology: Gatifloxacin is a synthetic broad-spectrum 8-methoxyfluoroquinolone antibacterial agent for oral or intravenous administration. is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian. Gatifloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It should be used only to treat or prevent infections that are proven or strongly suspected to be caused by bacteria.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites
• Absorption: Well absorbed from the gastrointestinal tract after oral administration with absolute bioavailability of gatifloxacin is 96%
• Half Life: 7-14 hours
• Protein Binding: 20%
• References: Park-Wyllie LY, Juurlink DN, Kopp A, Shah BR, Stukel TA, Stumpo C, Dresser L, Low DE, Mamdani MM: Outpatient gatifloxacin therapy and dysglycemia in older adults. N Engl J Med. 2006 Mar 30;354(13):1352-61. Epub 2006 Mar 1. [Pubmed] ; Gurwitz JH: Serious adverse drug effects--seeing the trees through the forest. N Engl J Med. 2006 Mar 30;354(13):1413-5. Epub 2006 Mar 1. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1340

Research Area: Infection
Biological Activity:
Gatifloxacin (Gatiflo, Tequin and Zymar), is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial enzymes DNA gyrase and topoisomerase IV. [1]

Toronto Research Chemicals - G250000

An antibacterial.

参考文献

• Park-Wyllie LY, Juurlink DN, Kopp A, Shah BR, Stukel TA, Stumpo C, Dresser L, Low DE, Mamdani MM: Outpatient gatifloxacin therapy and dysglycemia in older adults. N Engl J Med. 2006 Mar 30;354(13):1352-61. Epub 2006 Mar 1. Pubmed
• Gurwitz JH: Serious adverse drug effects--seeing the trees through the forest. N Engl J Med. 2006 Mar 30;354(13):1413-5. Epub 2006 Mar 1. Pubmed
• http://en.wikipedia.org/wiki/Gatifloxacin
• Bauernfeind, A.: J. Antimicro. Chemother., 40, 639 (1997)
• Fukuda, H., et al.: Antimicrob. Ag. Chemother., 42, 1917 (1997)
• Eur. Pat., 1987, Sankyo, 241 206; CA, 110, 135095, (synth, activity)
• Hosaka, M. et al., Antimicrob. Agents Chemother., 1992, 36, 2108; 1996, 40, 2756, (activity, pharmacol)
• Casta~ner, J. et al., Drugs of the Future, 1993, 18, 203
• Wakabayashi, E. et al., Antimicrob. Agents Chemother., 1994, 38, 594, (activity)
• Perry, C.M. et al., Drugs, 1999, 58, 683, (rev)
• Dalhoff, A., Expert Opin. Invest. Drugs, 1999, 8, 123