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

• ChemBase ID: 164784
• Molecular Formular: C17H18FN3O6S
• Molecular Mass: 411.4047232
• Monoisotopic Mass: 411.09003453
• SMILES: c1(c(cc2c(c1)n(cc(c2=O)C(=O)O)C1CC1)F)N1CCN(CC1)S(=O)(=O)O
• Canonical SMILES: Fc1cc2c(cc1N1CCN(CC1)S(=O)(=O)O)n(cc(c2=O)C(=O)O)C1CC1
• InChI: InChI=1S/C17H18FN3O6S/c18-13-7-11-14(21(10-1-2-10)9-12(16(11)22)17(23)24)8-15(13)19-3-5-20(6-4-19)28(25,26)27/h7-10H,1-6H2,(H,23,24)(H,25,26,27)
• InChIKey: SDLYZOYQWKDWJG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-cyclopropyl-6-fluoro-4-oxo-7-(4-sulfopiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: 1-cyclopropyl-6-fluoro-4-oxo-7-(4-sulfopiperazin-1-yl)quinoline-3-carboxylic acid
• Synonyms: 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-sulfo-1-piperazinyl)-3-quinolinecarboxylic Acid; Sulfociprofloxacin; 4-Sulfociprofloxacin; BAY-s 9435; Ciprofloxacin Piperazinyl-N4-sulfate

Database IDs

• CAS Number: 105093-21-8
• PubChem SID: 162258919
• PubChem CID: 128781

CALCULATED PROPERTIES

• Acid pKa: -1.5395986
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.7046739
• LogD (pH = 7.4): -2.9556406
• Log P: -0.38293776
• Molar Refractivity: 98.3456 cm^3
• Polarizability: 36.90127 Å^3
• Polar Surface Area: 118.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White to Pale Beige Solid
• Melting Point: 230-234°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C482525

A metabolite of the fluorinated quinolone antibacterial Ciprofloxacin (C482500).

REFERENCES

• Hoffken, G., et al.: Antimicrob. Ag. Chemother., 27, 375 (1985)
• Scully, B.E., et al.: Lancet, 1, 819 (1986)