6-fluoro-2-methyl-7-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

• ChemBase ID: 176764
• Molecular Formular: C18H20FN3O4
• Molecular Mass: 361.3675032
• Monoisotopic Mass: 361.14378436
• SMILES: Fc1c2c3c(cc1N1CCN(CC1)C)c(=O)c(cn3C(CO2)C)C(=O)O
• Canonical SMILES: CN1CCN(CC1)c1cc2c(=O)c(cn3c2c(c1F)OCC3C)C(=O)O
• InChI: InChI=1S/C18H20FN3O4/c1-10-9-26-17-14(19)13(21-5-3-20(2)4-6-21)7-11-15(17)22(10)8-12(16(11)23)18(24)25/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)
• InChIKey: FHAKLRRIGREDDW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-fluoro-2-methyl-7-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
• IUPAC Traditional name: 6-fluoro-2-methyl-7-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
• Synonyms: 10-Fluoro-2,3-dihydro-3-methyl-9-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid; 9-Piperazino Ofloxacin

Database IDs

• CAS Number: 197291-75-1
• PubChem SID: 164232674
• PubChem CID: 71751685

CALCULATED PROPERTIES

• Acid pKa: 5.6384373
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 0.48599425
• LogD (pH = 7.4): -0.12738709
• Log P: 0.62543994
• Molar Refractivity: 94.9359 cm^3
• Polarizability: 34.8209 Å^3
• Polar Surface Area: 73.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P480450

A degradation product of Ofloxacin (O245750). Ofloxacin impurity D. A regioisomer of Ofloxacin.

REFERENCES

• Fierens, C., et al.: J. Pharm. Biomed. Anal., 22, 763 (2000)
• Kitade, T., et al.: Chem. Pharm. Bull., 51, 53 (2000)
• Liang, Y., et al.: Anal. Chim. Acta, 510, 21 (2000)