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

• ChemBase ID: 72866
• Molecular Formular: C19H18ClF2N3O3
• Molecular Mass: 409.8143264
• Monoisotopic Mass: 409.10047557
• SMILES: c1(c(c(c2c(c1)c(=O)c(cn2C1[C@H](C1)F)C(=O)O)Cl)N1CC2([C@@H](C1)N)CC2)F
• Canonical SMILES: F[C@H]1CC1n1cc(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-RDWQBYKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(7S)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[(2S)-2-fluorocyclopropyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: 7-[(7S)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[(2S)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid
• Synonyms: DU 6859A; DU 6859; DU-6859; LS-184401; Sitafloxacin

Database IDs

• CAS Number: 127254-12-0
• PubChem SID: 162037787
• PubChem CID: 73011

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

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2152

Research Area: Infection
Biological Activity:
Sitafloxacin is a new-generation, broad-spectrum oral fluoroquinolone antibiotic.It is very active against many Gram-positive, Gram-negative and anaerobic clinical isolates, including strains resistant to other fluoroquinolones, was recently approved in Japan for the treatment of respiratory and urinary tract infections. Sitafloxacin is active against methicillin-resistant staphylococci, Streptococcus pneumoniae and other streptococci with reduced susceptibility to levofloxacin and other quinolones and enterococci. [1][2]

REFERENCES

• Anderson DL.Drugs Today (Barc). 2008 Jul; 44(7):489-501