1-cyclopropyl-6-fluoro-7-(4-formylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 169373
• Molecular Formular: C18H18FN3O4
• Molecular Mass: 359.3516232
• Monoisotopic Mass: 359.12813429
• SMILES: c1(c(cc2c(c1)n(cc(c2=O)C(=O)O)C1CC1)F)N1CCN(CC1)C=O
• Canonical SMILES: O=CN1CCN(CC1)c1cc2c(cc1F)c(=O)c(cn2C1CC1)C(=O)O
• InChI: InChI=1S/C18H18FN3O4/c19-14-7-12-15(8-16(14)21-5-3-20(10-23)4-6-21)22(11-1-2-11)9-13(17(12)24)18(25)26/h7-11H,1-6H2,(H,25,26)
• InChIKey: KCXCSXLUYCTARV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-cyclopropyl-6-fluoro-7-(4-formylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: 1-cyclopropyl-6-fluoro-7-(4-formylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
• Synonyms: Formylciprofloxacin (M4); 1-Cyclopropyl-6-fluoro-7-(4-formyl-1-piperazinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid; Formyl Ciprofloxacin

Database IDs

• CAS Number: 93594-39-9
• PubChem SID: 162263505
• PubChem CID: 4182953

CALCULATED PROPERTIES

• Acid pKa: 6.0597453
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.0090548
• LogD (pH = 7.4): -0.24212442
• Log P: 1.114731
• Molar Refractivity: 93.0148 cm^3
• Polarizability: 33.862663 Å^3
• Polar Surface Area: 81.16 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Hot Methanol; Hot Water
• Apperance: Pale Yellow Solid
• Melting Point: >280°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F698950

A metabolite of the fluorinated quinolone antibacterial Ciprofloxacin.

REFERENCES

• Tiefenbacher, E., et al.: J. Pharm. Sci., 83, 463 (1994)
• Parshikov, I., et al.: App. Microbiol. Biotechnol., 56, 474 (1994)