1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

• ChemBase编号: 350
• 分子式: C15H17FN4O3
• 平均质量: 320.3188832
• 单一同位素质量: 320.12846864
• SMILES: Fc1c(N2CCNCC2)nc2n(CC)cc(c(=O)c2c1)C(=O)O
• Canonical SMILES: CCn1cc(C(=O)O)c(=O)c2c1nc(N1CCNCC1)c(c2)F
• InChI: InChI=1S/C15H17FN4O3/c1-2-19-8-10(15(22)23)12(21)9-7-11(16)14(18-13(9)19)20-5-3-17-4-6-20/h7-8,17H,2-6H2,1H3,(H,22,23)
• InChIKey: IDYZIJYBMGIQMJ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
• IUPAC传统名: enoxacin
• 商标名: Penetrex
• 别名: 1-乙基-6-氟-1,4-二氢-4-氧代-7-(1-哌嗪基)-1,8-萘啶-3-羧酸; 依诺沙星; Enoxacin; Almitil; Bactidan; Bactidron; Comprecin; Enoksetin; Enoxen; Enroxil; Enoxin; Enoxor; Enoxacin(Penetrex); 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic Acid; Enofloxacin; Enofloxacine; Flumark; NSC 629661; PD 107779; Penetrex; 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; Enoxacin; 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[1-piperazinyl]-1,8-naphthyridine-3-carboxylic acid

登记号

• CAS号: 74011-58-8
• MDL号: MFCD00133308
• PubChem SID: 160963813; 24894528; 46507505
• PubChem CID: 3229

理论计算性质

JChem

• Acid pKa: 5.50139
• 质子受体: 7
• 质子供体: 2
• LogD (pH = 5.5): -1.20762
• LogD (pH = 7.4): -0.99097043
• Log P: -0.98305196
• 摩尔折射率: 83.9469 cm^3
• 极化性: 30.31111 Å^3
• 极化表面积: 85.77 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: -0.97
• LOG S: -2.47
• 溶解度: 1.09e+00 g/l

分子性质

理化性质

• 溶解度: 3.43 g/L; Sparingly soluble in Chloroform and Methanol
• 外观: Off-White to Pale Yellow Solid
• 熔点: 216-218°C; 220-224°C
• 疏水性(logP): -1.596; 2.3

安全信息

• 保存条件: -20°C; 2-8°C; Refrigerator
• RTECS编号: QN2800000
• 德国WGK号: 2
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... CYP1A2(1544)

产品相关信息

• 纯度: 95%
• 级别: analytical standard
• 成盐信息: Free Basef

详细说明

MP Biomedicals - 02195045

(1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-
[1-piperazinyl]-1,8-naphthyridine-3-carboxylic acid)

DrugBank - DB00467

• Drug Groups: approved
• Description: A broad-spectrum 6-fluoronaphthyridinone antibacterial agent (fluoroquinolones) structurally related to nalidixic acid. [PubChem]
• Indication: For the treatment of adults (≥18 years of age) with the following infections caused by susceptible strains of the designated microorganisms: (1) uncomplicated urethral or cervical gonorrhea due to Neisseria gonorrhoeae, (2) uncomplicated urinary tract infections (cystitis) due to Escherichia coli, Staphylococcus epidermidis, or Staphylococcus saprophyticus, and (3) complicated urinary tract infections due to Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Staphylococcus epidermidis, or Enterobacter cloacae.
• Pharmacology: Enoxacin is a quinolone/fluoroquinolone antibiotic. Enoxacin 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. Enoxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. Enoxacin may be active against pathogens resistant to drugs that act by different mechanisms.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic. Some isozymes of the cytochrome P-450 hepatic microsomal enzyme system are inhibited by enoxacin. After a single dose, greater than 40% was recovered in urine by 48 hours as unchanged drug.
• Absorption: Rapidly absorbed following oral administration, with an absolute oral bioavailability of approximately 90%.
• Half Life: Plasma half-life is 3 to 6 hours.
• Protein Binding: Enoxacin is approximately 40% bound to plasma proteins in healthy subjects and is approximately 14% bound to plasma proteins in patients with impaired renal function.
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1756

Research Area: Infection
Biological Activity:
Enoxacin(Penetrex) is an oral broad-spectrum fluoroquinolone antibacterial agent used in the treatment of urinary tract infections and gonorrhea. Insomnia is a common adverse effect. [1]

Sigma Aldrich - E3764

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
亲水性氟喹诺酮抗生素。NorA（金黄色葡萄球菌内的一种能量依赖性药外排泵）的底物。NorA 表达是造成某些耐药菌感染的原因。
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. E3764.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - E557600

A fluororquinolone antibacterial used to treat urinary tract infections and gonorrhea.

参考文献

• http://en.wikipedia.org/wiki/Enoxacin
• Liu, A., et al.: Antimicrob. Agents Chemother., 54, 1393 (2010)
• Chen, P., et al.: Drug Test Anal., 2, 24 (2010)
• Gohil, V., et al.: Nat., Biotechnol., 28, 249 (2010)