1-cyclopropyl-6-fluoro-7-[(1S,4S)-5-(2H3)methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; methanesulfonic acid

• ChemBase ID: 165366
• Molecular Formular: C20H24FN3O6S
• Molecular Mass: 453.4844632
• Monoisotopic Mass: 453.13698472
• SMILES: c12c(c(=O)c(cn1C1CC1)C(=O)O)cc(c(c2)N1[C@H]2CN([C@@H](C1)C2)C)F.S(=O)(=O)(C)O
• Canonical SMILES: CS(=O)(=O)O.CN1C[C@H]2C[C@@H]1CN2c1cc2c(cc1F)c(=O)c(cn2C1CC1)C(=O)O
• InChI: InChI=1S/C19H20FN3O3.CH4O3S/c1-21-7-12-4-11(21)8-22(12)17-6-16-13(5-15(17)20)18(24)14(19(25)26)9-23(16)10-2-3-10;1-5(2,3)4/h5-6,9-12H,2-4,7-8H2,1H3,(H,25,26);1H3,(H,2,3,4)/t11-,12-;/m0./s1
• InChIKey: APFDJSVKQNSTKF-FXMYHANSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-cyclopropyl-6-fluoro-7-[(1S,4S)-5-(^2H₃)methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; methanesulfonic acid
• IUPAC Traditional name: 1-cyclopropyl-6-fluoro-7-[(1S,4S)-5-(^2H₃)methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-4-oxoquinoline-3-carboxylic acid; methanesulfonic acid
• Synonyms: Danofloxacin-d3 Methanesulfonate; CP-76136-27-d3; Advocin-d3; Danofloxacin-d3 Mesylate; 1-Cyclopropyl-6-fluoro-1,4-dihydro-7-[(1S,4S)-5-(methyl-d3)-2,5-diazabicyclo[2.2.1]hept-2-yl]-4-oxo-3-quinolinecarboxylic Acid Mesylate

Database IDs

• PubChem SID: 162259499
• PubChem CID: 46780559

CALCULATED PROPERTIES

• Acid pKa: 5.6469007
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.5341455
• LogD (pH = 7.4): 0.17434801
• Log P: 0.7120464
• Molar Refractivity: 95.4709 cm^3
• Polarizability: 35.21171 Å^3
• Polar Surface Area: 64.09 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Light Tan Solid
• Melting Point: >250°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D153402

Labelled fluorinated quinolone antibacterial.

REFERENCES

• Giles, C.J., et al.: Vet. Rec., 128, 296 (1991)
• Sunderland, S.J., et al.: Res. Vet. Sci., 74, 171 (1991)