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

• ChemBase ID: 166511
• Molecular Formular: C17H19ClFN3O4
• Molecular Mass: 383.8018632
• Monoisotopic Mass: 383.104812
• SMILES: C1CNCCN1c1c2c3c(cc1F)c(=O)c(cn3[C@H](CO2)C)C(=O)O.Cl
• Canonical SMILES: Fc1cc2c3c(c1N1CCNCC1)OC[C@@H](n3cc(c2=O)C(=O)O)C.Cl
• InChI: InChI=1S/C17H18FN3O4.ClH/c1-9-8-25-16-13-10(15(22)11(17(23)24)7-21(9)13)6-12(18)14(16)20-4-2-19-3-5-20;/h6-7,9,19H,2-5,8H2,1H3,(H,23,24);1H/t9-;/m0./s1
• InChIKey: IOFZKWNXVPUJLW-FVGYRXGTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-7-fluoro-2-methyl-10-oxo-6-(piperazin-1-yl)-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-10-oxo-6-(piperazin-1-yl)-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraene-11-carboxylic acid hydrochloride
• Synonyms: (3S)-9-Fluoro-2,3-dihydro-3-methyl-7-oxo-10-(1-piperazinyl)-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid Hydrochloride; DN 5455 Hydrochloride; Desmethyl Levofloxacin Hydrochloride

Database IDs

• PubChem SID: 162260644
• PubChem CID: 71315760

CALCULATED PROPERTIES

• Acid pKa: 5.5710354
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.4719325
• LogD (pH = 7.4): -1.2257148
• Log P: -1.2204981
• Molar Refractivity: 89.6412 cm^3
• Polarizability: 32.998604 Å^3
• Polar Surface Area: 82.11 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D292050

A metabolite of Levofloxacin.

REFERENCES

• Sudo, K., et al.: Xenobiotica, 16, 72 (1986)
• Wong, F., et al.: Drug Metab. Dispos., 18, 1103 (1986)
• Aminimanizani, A., et al.: J. Clin. Pharmacokinet., 40, 169 (1986)
• Athamna, A., et al.: J. Antimicrob. Chemother., 53, 247 (1986)
• Tanaka, M., et al.: J