acetic acid 4-{11-carboxy-7-fluoro-2-methyl-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraen-6-yl}-1-methylpiperazin-1-ium-1-olate

• ChemBase ID: 175811
• Molecular Formular: C20H24FN3O7
• Molecular Mass: 437.4188632
• Monoisotopic Mass: 437.15982834
• SMILES: c12c3c(=O)c(cn1C(COc2c(c(c3)F)N1CC[N+](CC1)(C)[O-])C)C(=O)O.CC(=O)O
• Canonical SMILES: Fc1cc2c3c(c1N1CC[N+](CC1)([O-])C)OCC(n3cc(c2=O)C(=O)O)C.CC(=O)O
• InChI: InChI=1S/C18H20FN3O5.C2H4O2/c1-10-9-27-17-14-11(16(23)12(18(24)25)8-21(10)14)7-13(19)15(17)20-3-5-22(2,26)6-4-20;1-2(3)4/h7-8,10H,3-6,9H2,1-2H3,(H,24,25);1H3,(H,3,4)
• InChIKey: WOXKVUYCBCCDTD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: acetic acid 4-{11-carboxy-7-fluoro-2-methyl-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraen-6-yl}-1-methylpiperazin-1-ium-1-olate
• IUPAC Traditional name: acetic acid 4-{11-carboxy-7-fluoro-2-methyl-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraen-6-yl}-1-methylpiperazin-1-ium-1-olate
• Synonyms: 9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-4-oxido-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid Acetic Acid Salt; Ofloxacin N-Oxide Acetic Acid Salt (Mixture of Diastereomers)

Database IDs

• CAS Number: 104721-52-0
• PubChem SID: 164231721
• PubChem CID: 46782613

CALCULATED PROPERTIES

• Acid pKa: 5.8750095
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 0.28101906
• LogD (pH = 7.4): -1.099791
• Log P: 0.43397444
• Molar Refractivity: 96.9808 cm^3
• Polarizability: 35.04717 Å^3
• Polar Surface Area: 96.96 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 215-220°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer

DETAILS

Toronto Research Chemicals - O245755

A metabolite of Ofloxacin.

REFERENCES

• Uematsu, T., et al.: Eur. J. Clin. Pharmacol., 40, 581 (1991)
• Uematsu, T., et al.: Ther. Drug Monit., 17, 101 (1991)
• Ballesteros, O., et al.: J. Pharm. Biomed. Anal., 30, 1103 (1991)
• Kitade, T., et al.: Chem. Pharm. Bull., 51, 53 (1991)