7-[(1R,5S,6R)-6-amino(2,2,4,4-2H4)-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; methanesulfonic acid

• ChemBase ID: 179357
• Molecular Formular: C21H19F3N4O6S
• Molecular Mass: 512.4589696
• Monoisotopic Mass: 512.09774001
• SMILES: c1(c(cc2c(n1)n(cc(c2=O)C(=O)O)c1ccc(cc1F)F)F)N1C[C@H]2[C@H](C1)[C@@H]2N.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.N[C@@H]1[C@@H]2[C@@H]1CN(C2)c1nc2c(cc1F)c(=O)c(cn2c1ccc(cc1F)F)C(=O)O
• InChI: InChI=1S/C20H15F3N4O3.CH4O3S/c21-8-1-2-15(13(22)3-8)27-7-12(20(29)30)17(28)9-4-14(23)19(25-18(9)27)26-5-10-11(6-26)16(10)24;1-5(2,3)4/h1-4,7,10-11,16H,5-6,24H2,(H,29,30);1H3,(H,2,3,4)/t10-,11?,16+;/m0./s1
• InChIKey: DYNZICQDCVYXFW-OZNIDUIKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,5S,6R)-6-amino(2,2,4,4-^2H₄)-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; methanesulfonic acid
• IUPAC Traditional name: 7-[(1R,5S,6R)-6-amino(2,2,4,4-^2H₄)-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid; methanesulfonic acid
• Synonyms: 7-[(1α,5α,6α)-6-Amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid-d4 Methanesulfonate; CP 99219-d4; CP 99219-27-d4; Trovafloxacin-d4 Methanesulfonate; Trovafloxacin-d4 Monomethanesulfonate; Trovan-d4; Trovafloxacin-d4 Mesylate

Database IDs

• PubChem SID: 164235267
• PubChem CID: 71752874

CALCULATED PROPERTIES

• Acid pKa: 5.4131193
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.057143982
• LogD (pH = 7.4): 0.13973176
• Log P: 0.13645041
• Molar Refractivity: 101.0404 cm^3
• Polarizability: 36.81934 Å^3
• Polar Surface Area: 99.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T893002

Labelled Trovafloxacin (T893000). Fluorinated quinolone antibacterial. Trovafloxacin mesylate blocks the activity of DNA gyrase and topoisomerase IV, enzymes essential in the repliction, transcription, and repair of bacterial DNA.

REFERENCES

• Neu, H.C., et al.: Clin. Antimicrob. Agents Chemother., 38, 2615 (1994)
• Liguori, M.J., et al.: Hepatology, 41, 177 (1994)