CAS 70458-96-7|Norfloxacin|Chibroxin|1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid|norfloxacin|Noroxin|Chibroxin|MK-366|Sebercim|Baccidal|Norfloxacin(Norxacin)|1-E...

基本信息

化学结构

分子式

C₁₆H₁₈FN₃O₃

分子量

319.3308232

精确质量

319.13321967

电荷

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

Canonic Smiles

CCn1cc(C(=O)O)c(=O)c2c1cc(N1CCNCC1)c(c2)F

Isomeric Smiles

Fc1c(N2CCNCC2)cc2n(CC)cc(c(=O)c2c1)C(=O)O

计算属性

JChem

Acid pKa

5.7689314

质子受体

质子供体

LogD (pH = 5.5)

-1.2569264

LogD (pH = 7.4)

-0.92003995

Log P

-0.92048955

摩尔折射率

85.4768

极化性

31.151457

极化表面积

72.88

可自由旋转的化学键

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

数据来源

名称和标识

别名

NorfloxacinChibroxinMK-366SebercimBaccidalNorfloxacin(Norxacin)1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[1-piperazinyl]-3-quinoline-carboxylic acid1-Ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylic acidNorfloxacin诺氟沙星1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid1-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1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazino-3-quinolinecarboxylic acid1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acidN-DesmethylpefloxacinChibroxineBarazanZoroxinN-DemethylpefloxacinNorxacinEspedenNoroxinAmicrobinNalionFortimaxFulgramEsclebinLexinor

商标名

ChibroxinNoroxin

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

名称和标识

数据登录号

EC号

CAS号

PubChem CID

MDL号

PubChem SID

248605994650863416096439324897917

数据登录号

化合物性质

药理学性质

human ... CYP1A2(1544)rat ... Gabra1(29705)

Inhibitor of the A subunit of bacterial DNA gyrase, an enzyme which is essential for DNA replication

化合物性质

分子相关蛋白质

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分子图谱

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描述信息

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]

MP Biomedicals

02155949

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

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

33899

TRC

N681000

Pefloxacin derivative as antibacterial. Fluorinated quinolone antibacterial.

描述信息

参考文献

PubChem文献

数据源提供

• 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

• Holmes, B., et al.: Drugs, 30, 482 (1980)

• Hirai, K., et al.: Antimicrob. Agents Chemother., 19, 188 (1980)

• Koga, H., et al.: J. Med. Chem., 23, 1358 (1980)

• Clark, R.L. et al., Fundam. Appl. Toxicol., 1986, 7, 272, (reprod, tox)

• Pauliulconis, L.T. et al., J. Pharm. Sci., 1984, 73, 99, (hplc)

• Toffoli, P. et al., Acta Cryst. C, 1987, 43, 1745, (Pefloxacin, cryst struct)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 188; 191

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BAB625

• New Gener. Quinolones, 1990, (Eds. Siporin, C. et al), M. Dekker (see Infect. Dis. Ther. v5 1990), 1990, (book)

• Hirai, K. et al., Antimicrob. Agents Chemother., 1981, 19, 188, (pharmacol)

• Irikura, T. et al., Chemotherapy (Tokyo), 1981, 29, 766, (tox)

• Holmes, B. et al., Drugs, 1985, 30, 482, (rev)

• Buckingham, D.A. et al., Aust. J. Chem., 1990, 43, 31, (pmr, cmr, props, tautom)

• Koga, H. et al., J. Med. Chem., 1980, 23, 1358, (synth)

• Eur. Pat., 1985, Farmades, 155 006; CA, 104, 109688x, (synth, norfloxacin succinil)

• Bressolle, F. et al., Clin. Pharmacokinet., 1994, 27, 418, (pharmacokinet, rev)

• Hussain, M.S. et al., J. Chromatogr., B: Biomed. Appl., 1995, 663, 379, (hplc)

• Goneftou, Y. et al., C. R. Hebd. Seances Acad. Sci., 1981, 292, 37

• Mazuel, C., Anal. Profiles Drug Subst., 1991, 20, 557, (rev)

• Wallis, S.C. et al., Aust. J. Chem., 1994, 47, 799, (cryst struct, cmr)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 5195; 5833, (synonyms)

• Burnie, J., Drugs of Today (Barcelona), 1984, 20, 391, (rev)

• Wise, R., J. Antimicrob. Chemother., Suppl. B, 1984, 13, 59, (rev)

• Gonzalez, J.P. et al., Drugs, 1989, 37, 628, (Pefloxacin, rev)

参考文献

生物活性

PubChem BioAssay

生物活性