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

General Information

Structure

Molecular Formula

C₁₆H₁₈FN₃O₃

Molecular Mass

319.3308232

Exact Mass

319.13321967

Charge

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

Calculated Properties

JChem

Acid pKa

5.7689314

H Acceptors

H Donor

LogD (pH = 5.5)

-1.2569264

LogD (pH = 7.4)

-0.92003995

Log P

-0.92048955

Molar Refractivity

85.4768

Polarizability

31.151457

Polar Surface Area

72.88

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

-0.47

LOG S

-2.5

Solubility (Water)

1.01e+00 g/l

Data Source

Names and Identifiers

Synonyms

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

Brand Name

ChibroxinNoroxin

IUPAC name

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

IUPAC Traditional name

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

Names and Identifiers

Registration numbers

EC Number

CAS Number

PubChem CID

MDL Number

PubChem SID

248605994650863416096439324897917

Registration numbers

Properties

Product Information

Pharmacology Properties

Gene Information

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

Mechanism of Action

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

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

References

Bioactivity

PubChem BioAssay

Bioactivity