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

• ChemBase ID: 166354
• Molecular Formular: C20H21F4N3O5
• Molecular Mass: 459.3914528
• Monoisotopic Mass: 459.14173367
• SMILES: c1c(c(cc2c1n(cc(c2=O)C(=O)O)C1CC1)F)N1CC(NCC1)C.C(F)(F)(F)C(=O)O
• Canonical SMILES: OC(=O)C(F)(F)F.CC1NCCN(C1)c1cc2c(cc1F)c(=O)c(cn2C1CC1)C(=O)O
• InChI: InChI=1S/C18H20FN3O3.C2HF3O2/c1-10-8-21(5-4-20-10)16-7-15-12(6-14(16)19)17(23)13(18(24)25)9-22(15)11-2-3-11;3-2(4,5)1(6)7/h6-7,9-11,20H,2-5,8H2,1H3,(H,24,25);(H,6,7)
• InChIKey: URJUNYOPXJPQGS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-cyclopropyl-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; trifluoroacetic acid
• IUPAC Traditional name: 1-cyclopropyl-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid; trifluoroacetic acid
• Synonyms: 1-Cyclopropyl-6-fluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid Trifluoroacetate; AM 1121; CNV 8912; CNV 97100; ITV 8912; Desmethoxy Gatifloxacin Trifluoroacetate

Database IDs

• CAS Number: 93107-32-5
• PubChem SID: 162260487
• PubChem CID: 46781144

CALCULATED PROPERTIES

• Acid pKa: 5.7555933
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.7457407
• LogD (pH = 7.4): -0.41565913
• Log P: -0.417875
• Molar Refractivity: 92.3582 cm^3
• Polarizability: 34.095585 Å^3
• Polar Surface Area: 72.88 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 233-235°C

DETAILS

Toronto Research Chemicals - D290450

Gatifloxacin derivative; a new antimycobacterial.

REFERENCES

• Sanchez, J., et al.: J. Med. Chem., 35, 361 (1992)
• Cecchetti, V., et al.: Bioorg. Med. Chem., 7, 2465 (1992)
• Alovero, F., et al.: Antimicrob. Agents Chemother., 44, 320 (1992)