7-[(7S)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 177779
• Molecular Formular: C19H18ClF2N3O3
• Molecular Mass: 409.8143264
• Monoisotopic Mass: 409.10047557
• SMILES: C12(CN(C[C@H]1N)c1c(cc3c(c1Cl)n(cc(c3=O)C(=O)O)[C@@H]1C[C@@H]1F)F)CC2
• Canonical SMILES: F[C@H]1C[C@H]1n1cc(C(=O)O)c(=O)c2c1c(Cl)c(N1C[C@H](C3(C1)CC3)N)c(c2)F
• InChI: InChI=1S/C19H18ClF2N3O3/c20-14-15-8(17(26)9(18(27)28)5-25(15)12-4-10(12)21)3-11(22)16(14)24-6-13(23)19(7-24)1-2-19/h3,5,10,12-13H,1-2,4,6-7,23H2,(H,27,28)/t10-,12+,13+/m0/s1
• InChIKey: PNUZDKCDAWUEGK-CYZMBNFOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(7S)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: sitafloxacin
• Synonyms: 7-[(7S)-7-Amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Hydrate; Sitafloxacin Sesquihydrate

Database IDs

• CAS Number: 163253-35-8
• PubChem SID: 164233689
• PubChem CID: 461399

CALCULATED PROPERTIES

• Acid pKa: 5.699729
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.46243346
• LogD (pH = 7.4): -0.1614805
• Log P: -0.16889024
• Molar Refractivity: 99.0881 cm^3
• Polarizability: 36.969666 Å^3
• Polar Surface Area: 86.87 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Base; DMSO
• Apperance: Off-White Solid
• Melting Point: 145-147°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - S490920

Antibacterial

REFERENCES

• Suzuki, T., et al.: Anal. Sci., 16, 343 (2000)
• Payne G., et al.: Brit. J. Clin. Pharmacol., 59, 244 (2000)
• Okuda J., et al.: Microbiol. immunol., 51, 467 (2000)
• Okumura R., et al.: Chemother., 55, 262 (2000)