(2R)-7-fluoro-2-methyl-6-[4-(2H3)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: 175809
• 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-/m1/s1
• InChIKey: GSDSWSVVBLHKDQ-SNVBAGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-7-fluoro-2-methyl-6-[4-(^2H₃)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: (2R)-7-fluoro-2-methyl-6-[4-(^2H₃)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: (3R)-9-Fluoro-2,3-dihydro-3-methyl-10-[4-(methyl-d3)-1-piperazinyl]-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid; (+)-Ofloxacin-d3; (R)-(+)-Ofloxacin-d3; D-Ofloxacin-d3; DR 3354-d3; d-Levofloxacin-d3; (R)-Ofloxacin-d3

Database IDs

• PubChem SID: 164231719
• PubChem CID: 71751296

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: 34.82272 Å^3
• Polar Surface Area: 73.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - O245742

A labelled fluorinated quinolone antibacterial. An enantiomer of Levofloxacin (L360000).

REFERENCES

• Hwangbo, H.J. et al.: Eur. J. Pharmac. Sci., 18, 197 (203)
• Gascon, A.R. et al.: J. Clin. Pharmacol, 40, 869 (203)
• Monk, J.P., et al.: Drugs, 33, 346 (203)
• Drlica, K., Curr. Opin. Microbiol. 2, 504 (203)