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

• ChemBase ID: 122598
• Molecular Formular: C20H24FN3O6S
• Molecular Mass: 453.4844632
• Monoisotopic Mass: 453.13698472
• SMILES: c1(c(=O)c2c(n(c1)C1CC1)cc(N1[C@H]3C[C@H](N(C3)C)C1)c(c2)F)C(=O)O.S(=O)(=O)(O)C
• 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-;/m1./s1
• InChIKey: APFDJSVKQNSTKF-MNMPKAIFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-cyclopropyl-6-fluoro-7-[(1R,4R)-5-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-[(1R,4R)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-4-oxoquinoline-3-carboxylic acid mesylate; 1-cyclopropyl-6-fluoro-7-[(1R,4R)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; methanesulfonic acid
• Synonyms: 1-cyclopropyl-6-fluoro-7-((1R,4R)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid compound with methanesulfonic acid (1:1); Monomethanesulfonate; Danofloxacin Mesylate

Database IDs

• CAS Number: 138808-76-1
• PubChem SID: 162216951
• PubChem CID: 11453793

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

Pharmacology Properties

• Mechanism of Action: DNA gyrase and topoisomerase IV inhibitor

Product Information

• Salt Data: Mesylate
• Description: Isomers
• Application(s): Used in treatment of respiratory disease; Veterinary antibacterial agent

DETAILS

InterBioScreen - BB_SC-4835

Isomers

REFERENCES

• Eur. Pat., 1989, Pfizer, 342 849; CA, 113, 6177m, (synth)
• Giles, C.J. et al., J. Vet. Pharmacol. Ther., 1991, 14, 400, (activity, pharmacokinet)
• McGuirk, P.R. et al., J. Med. Chem., 1992, 35, 611, (synth, sar)
• Schneider, R.P. et al., Biol. Mass. Spectrom., 1993, 22, 595, (hplc-ms)