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

• ChemBase编号: 930
• 分子式: C16H18FN3O3
• 平均质量: 319.3308232
• 单一同位素质量: 319.13321967
• SMILES: Fc1c(N2CCNCC2)cc2n(CC)cc(c(=O)c2c1)C(=O)O
• Canonical SMILES: CCn1cc(C(=O)O)c(=O)c2c1cc(N1CCNCC1)c(c2)F
• InChI: InChI=1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)
• InChIKey: OGJPXUAPXNRGGI-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-dihydroquinoline-3-carboxylic acid
• IUPAC传统名: norfloxacin; 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)quinoline-3-carboxylic acid; 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
• 商标名: Chibroxin; Noroxin
• 别名: 1-乙基-6-氟-1,4-二氢-4-氧代-7-(1-哌嗪基)-3-喹啉羧酸; 1-乙基-6-氟-1,4-二氢-4-氧代-7-哌嗪-3-喹啉羧酸; 诺氟沙星; Norfloxacin; 1-Ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylic acid; 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid; Amicrobin; Esclebin; Espeden; Fortimax; Fulgram; Lexinor; Nalion; Noroxin; Barazan; Chibroxine; N-Demethylpefloxacin; N-Desmethylpefloxacin; Norxacin; Zoroxin; Norfloxacin; 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[1-piperazinyl]-3-quinoline-carboxylic acid; 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid; 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazino-3-quinolinecarboxylic acid; Chibroxin; MK-366; Baccidal; Sebercim; Norfloxacin(Norxacin)

登记号

• CAS号: 70458-96-7
• EC号: 274-614-4
• MDL号: MFCD00079532
• PubChem SID: 46508634; 160964393; 24860599; 24897917
• PubChem CID: 4539

理论计算性质

JChem

• Acid pKa: 5.7689314
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): -1.2569264
• LogD (pH = 7.4): -0.92003995
• Log P: -0.92048955
• 摩尔折射率: 85.4768 cm^3
• 极化性: 31.151457 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: -0.47
• LOG S: -2.5
• 溶解度: 1.01e+00 g/l

分子性质

理化性质

• 溶解度: 1.78E+005 mg/L; DMSO; Methanol (Sparingly)
• 外观: Pale Yellow Solid
• 熔点: 210-211°C; 227-228°C
• 疏水性(logP): 2.1

安全信息

• 保存条件: -20°C; -20°C Freezer; 2-8°C
• 保存注意事项: IRRITANT
• RTECS编号: VB2005000
• 德国WGK号: 2
• TSCA收录: false
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... CYP1A2(1544)rat ... Gabra1(29705)
• 生物活性机理: Inhibitor of the A subunit of bacterial DNA gyrase, an enzyme which is essential for DNA replication

产品相关信息

• 纯度: ≥98% (TLC)
• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• 适用性: suitable for 1694 per US EPA
• 应用领域: Antibacterial agent
• Empirical Formula (Hill Notation): C16H18FN3O3

详细说明

MP Biomedicals - 02155949

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

DrugBank - DB01059

• Drug Groups: approved
• Description: A synthetic fluoroquinolone (fluoroquinolones) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA gyrase. [PubChem]
• Indication: For the treatment of urinary tract infection
• Pharmacology: Norfloxacin is a quinolone/fluoroquinolone antibiotic. Norfloxacin 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.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Via liver and kidney
• Absorption: Rapid
• Half Life: 3-4 hours
• Protein Binding: 10 and 15% (Serum protein binding)
• Elimination: Norfloxacin is eliminated through metabolism, biliary excretion, and renal excretion.; Renal excretion occurs by both glomerular filtration and tubular secretion as evidenced by the high rate of renal clearance (approximately 275 mL/min).
• References: Goldstein EJ: Norfloxacin, a fluoroquinolone antibacterial agent. Classification, mechanism of action, and in vitro activity. Am J Med. 1987 Jun 26;82(6B):3-17. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1509

Research Area: Infection
Biological Activity:
Norfloxacin(Norxacin) is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It functions by inhibiting DNA gyrase, a type II topoisomerase, and topoisomerase IV, enzymes necessary to separate bacterial DNA, thereby inhibiting cell division.This mechanism can also affect mammalian cell replication. [1] 

Sigma Aldrich - N9890

Biochem/physiol Actions
Norfloxacin blocks DNA replication by interfering with an ATP-induced structural transition of DNA complexed with DNA gyrase (topoisomerase).Mode of action: inhibits bacterial DNA replicationAntimicrobial spectrum: Gram-negative bacteria; less effective against Gram-positive bacteria

Sigma Aldrich - 33899

Biochem/physiol Actions
Norfloxacin blocks DNA replication by interfering with an ATP-induced structural transition of DNA complexed with DNA gyrase (topoisomerase).Mode of action: inhibits bacterial DNA replicationAntimicrobial spectrum: Gram-negative bacteria; less effective against Gram-positive bacteria
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - N681000

Pefloxacin derivative as antibacterial. Fluorinated quinolone antibacterial.

参考文献

• Goldstein EJ: Norfloxacin, a fluoroquinolone antibacterial agent. Classification, mechanism of action, and in vitro activity. Am J Med. 1987 Jun 26;82(6B):3-17. Pubmed
• http://en.wikipedia.org/wiki/Norfloxacin
• Koga, H., et al.: J. Med. Chem., 23, 1358 (1980)
• Hirai, K., et al.: Antimicrob. Agents Chemother., 19, 188 (1980)
• Holmes, B., et al.: Drugs, 30, 482 (1980)
• Koga, H. et al., J. Med. Chem., 1980, 23, 1358, (synth)
• Hirai, K. et al., Antimicrob. Agents Chemother., 1981, 19, 188, (pharmacol)
• Goneftou, Y. et al., C. R. Hebd. Seances Acad. Sci., 1981, 292, 37
• Irikura, T. et al., Chemotherapy (Tokyo), 1981, 29, 766, (tox)
• Burnie, J., Drugs of Today (Barcelona), 1984, 20, 391, (rev)
• Wise, R., J. Antimicrob. Chemother., Suppl. B, 1984, 13, 59, (rev)
• Pauliulconis, L.T. et al., J. Pharm. Sci., 1984, 73, 99, (hplc)
• Holmes, B. et al., Drugs, 1985, 30, 482, (rev)
• Eur. Pat., 1985, Farmades, 155 006; CA, 104, 109688x, (synth, norfloxacin succinil)
• Clark, R.L. et al., Fundam. Appl. Toxicol., 1986, 7, 272, (reprod, tox)
• Toffoli, P. et al., Acta Cryst. C, 1987, 43, 1745, (Pefloxacin, cryst struct)
• Gonzalez, J.P. et al., Drugs, 1989, 37, 628, (Pefloxacin, rev)
• Buckingham, D.A. et al., Aust. J. Chem., 1990, 43, 31, (pmr, cmr, props, tautom)
• New Gener. Quinolones, 1990, (Eds. Siporin, C. et al), M. Dekker (see Infect. Dis. Ther. v5 1990), 1990, (book)
• Mazuel, C., Anal. Profiles Drug Subst., 1991, 20, 557, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 188; 191
• Wallis, S.C. et al., Aust. J. Chem., 1994, 47, 799, (cryst struct, cmr)
• Bressolle, F. et al., Clin. Pharmacokinet., 1994, 27, 418, (pharmacokinet, rev)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 5195; 5833, (synonyms)
• Hussain, M.S. et al., J. Chromatogr., B: Biomed. Appl., 1995, 663, 379, (hplc)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BAB625