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

• ChemBase ID: 930
• Molecular Formular: C16H18FN3O3
• Molecular Mass: 319.3308232
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• 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
• Brand Name: Chibroxin; Noroxin
• Synonyms: 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); 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

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.7689314
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.2569264
• LogD (pH = 7.4): -0.92003995
• Log P: -0.92048955
• Molar Refractivity: 85.4768 cm^3
• Polarizability: 31.151457 Å^3
• Polar Surface Area: 72.88 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.47
• LOG S: -2.5
• Solubility (Water): 1.01e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1.78E+005 mg/L; DMSO; Methanol (Sparingly)
• Apperance: Pale Yellow Solid
• Melting Point: 210-211°C; 227-228°C
• Hydrophobicity(logP): 2.1

Safety Information

• Storage Condition: -20°C; -20°C Freezer; 2-8°C
• Storage Warning: IRRITANT
• RTECS: VB2005000
• German water hazard class: 2
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

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

Product Information

• Purity: ≥98% (TLC)
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Suitability: suitable for 1694 per US EPA
• Application(s): Antibacterial agent
• Empirical Formula (Hill Notation): C16H18FN3O3

DETAILS

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
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - N681000

Pefloxacin derivative as antibacterial. Fluorinated quinolone antibacterial.

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
• 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