(2S)-7-fluoro-2-methyl-6-[4-methyl(2H8)piperazin-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: 172279
• Molecular Formular: C18H20FN3O4
• Molecular Mass: 361.3675032
• Monoisotopic Mass: 361.14378436
• SMILES: C1CN(CCN1c1c2c3c(cc1F)c(=O)c(cn3[C@H](CO2)C)C(=O)O)C
• Canonical SMILES: CN1CCN(CC1)c1c(F)cc2c3c1OC[C@@H](n3cc(c2=O)C(=O)O)C
• InChI: InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)/t10-/m0/s1
• InChIKey: GSDSWSVVBLHKDQ-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-7-fluoro-2-methyl-6-[4-methyl(^2H₈)piperazin-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: (2S)-7-fluoro-2-methyl-6-[4-methyl(^2H₈)piperazin-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: (-)-(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl-d8)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid Hemihydrate; Levofloxacin-d8

Database IDs

• CAS Number: 1217716-71-6
• PubChem SID: 164228189
• PubChem CID: 46782054

CALCULATED PROPERTIES

• Acid pKa: 5.4470572
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 0.616237
• LogD (pH = 7.4): -0.2825112
• Log P: 0.65427977
• Molar Refractivity: 94.9359 cm^3
• Polarizability: 34.82393 Å^3
• Polar Surface Area: 73.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid
• Melting Point: 222-224°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L360002

Labelled S-(-)-Form of Ofloxacin. An antibiotic used against gram-negative organisms.

REFERENCES

• Kato, M., et al.: Arzneim.-Forsch., 42, 365 (1992)
• North, D.S., et al.: Pharmacotherapy, 18, 915 (1992)
• Hwang, D.G., et al.: Br. J. Ophthalmol., 87, 1004 (1992)