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

• ChemBase ID: 171008
• Molecular Formular: C16H18FN3O4
• Molecular Mass: 335.3302232
• Monoisotopic Mass: 335.12813429
• SMILES: c1c(c(cc2c1n(cc(c2=O)C(=O)O)CC)F)N1CCN(CC1)O
• Canonical SMILES: CCn1cc(C(=O)O)c(=O)c2c1cc(N1CCN(CC1)O)c(c2)F
• InChI: InChI=1S/C16H18FN3O4/c1-2-18-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)18)19-3-5-20(24)6-4-19/h7-9,24H,2-6H2,1H3,(H,22,23)
• InChIKey: BUZRYEUCJVTZNX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-ethyl-6-fluoro-7-(4-hydroxypiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: 1-ethyl-6-fluoro-7-(4-hydroxypiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
• Synonyms: 1-Ethyl-6-fluoro-1,4-dihydro-7-(4-hydroxy-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid; N-Hydroxy Norfloxacin; 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl-N-oxo)-3-quinolinecarboxylic Acid; N-Desmethylpefloxacin N-Oxide; Norfloxacin N-Oxide

Database IDs

• CAS Number: 109142-49-6
• PubChem SID: 164226918
• PubChem CID: 3031736

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.9600504
• LogD (pH = 7.4): -0.28130612
• Log P: 1.062883
• Molar Refractivity: 87.2414 cm^3
• Polarizability: 31.826172 Å^3
• Polar Surface Area: 84.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 6.0730886

DETAILS

Toronto Research Chemicals - N681010

A metabolite of Norfloxacin (N681000).

Toronto Research Chemicals - H948810

A metabolite of Norfloxacin (N681000).

REFERENCES

• Uno, T., et al.: J. Med. Chem., 33, 2929 (1990)