1-ethyl-6-fluoro-4-oxo-7-[(2,2,3,3,5,5,6,6-2H8)piperazin-1-yl]-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 175464
• Molecular Formular: C16H18FN3O3
• Molecular Mass: 319.3308232
• Monoisotopic Mass: 319.13321967
• SMILES: c1c(c(cc2c1n(cc(c2=O)C(=O)O)CC)F)N1CCNCC1
• 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-[(2,2,3,3,5,5,6,6-^2H₈)piperazin-1-yl]-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: 1-ethyl-6-fluoro-4-oxo-7-[(2,2,3,3,5,5,6,6-^2H₈)piperazin-1-yl]quinoline-3-carboxylic acid
• Synonyms: 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl-d8)-3-quinolinecarboxylic Acid; Baccidal-d8; Barazan-d8; Chibroxine-d8; N-Demethylpefloxacin-d8; N-Desmethylpefloxacin-d8; MK-366-d8; Norxacin-d8; Sebercim-d8; Zoroxin-d8; Norfloxacin-d8

Database IDs

• CAS Number: 1216601-32-9
• PubChem SID: 164231374
• PubChem CID: 57369361

CALCULATED PROPERTIES

• 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: 31.152702 Å^3
• Polar Surface Area: 72.88 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: Pale Yellow Solid
• Melting Point: 217-220°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N681002

Labelled Norfloxacin. Pefloxacin derivative as antibacterial. Fluorinated quinolone antibacterial.

REFERENCES

• 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)