(2S)-7-fluoro-2-methyl-6-{[2-(methylamino)ethyl]amino}-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid hydrochloride

• ChemBase ID: 166224
• Molecular Formular: C16H19ClFN3O4
• Molecular Mass: 371.7911632
• Monoisotopic Mass: 371.104812
• SMILES: C(CNC)Nc1c2c3c(cc1F)c(=O)c(cn3[C@H](CO2)C)C(=O)O.Cl
• Canonical SMILES: CNCCNc1c(F)cc2c3c1OC[C@@H](n3cc(c2=O)C(=O)O)C.Cl
• InChI: InChI=1S/C16H18FN3O4.ClH/c1-8-7-24-15-12(19-4-3-18-2)11(17)5-9-13(15)20(8)6-10(14(9)21)16(22)23;/h5-6,8,18-19H,3-4,7H2,1-2H3,(H,22,23);1H/t8-;/m0./s1
• InChIKey: XCUXHIUSNKPZPM-QRPNPIFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-7-fluoro-2-methyl-6-{[2-(methylamino)ethyl]amino}-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraene-11-carboxylic acid hydrochloride
• IUPAC Traditional name: (2S)-7-fluoro-2-methyl-6-{[2-(methylamino)ethyl]amino}-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraene-11-carboxylic acid hydrochloride
• Synonyms: (S)-9-Fluoro-2,3-dihydro-3-methyl-10-[[2-(methylamino)ethyl]amino]-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid Hydrochloride; N,N'-Desethylene Levofloxacin Hydrochloride

Database IDs

• PubChem SID: 162260357
• PubChem CID: 71315634

CALCULATED PROPERTIES

• Acid pKa: 5.53899
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.9920182
• LogD (pH = 7.4): -1.7511503
• Log P: -1.7561026
• Molar Refractivity: 87.3754 cm^3
• Polarizability: 31.883356 Å^3
• Polar Surface Area: 90.9 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 264-266°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D289350

Levofloxacin (L360000) impurity. A photodegradation product of Levofloxacin (L360000) in aqueous solution.

REFERENCES

• Yoshida, Y., et al.: Arzneim.-Forsch., 43, 601 (1993)