6-fluoro-1-(4-fluorophenyl)-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid hydrochloride

• ChemBase ID: 122600
• Molecular Formular: C20H18ClF2N3O3
• Molecular Mass: 421.8250264
• Monoisotopic Mass: 421.10047557
• SMILES: c1(c(=O)c2c(n(c1)c1ccc(cc1)F)cc(c(c2)F)N1CCNCC1)C(=O)O.Cl
• Canonical SMILES: Fc1ccc(cc1)n1cc(C(=O)O)c(=O)c2c1cc(N1CCNCC1)c(c2)F.Cl
• InChI: InChI=1S/C20H17F2N3O3.ClH/c21-12-1-3-13(4-2-12)25-11-15(20(27)28)19(26)14-9-16(22)18(10-17(14)25)24-7-5-23-6-8-24;/h1-4,9-11,23H,5-8H2,(H,27,28);1H
• InChIKey: KNWODGJQLCISLC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-fluoro-1-(4-fluorophenyl)-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid hydrochloride
• IUPAC Traditional name: sarafloxacin hydrochloride; 6-fluoro-1-(4-fluorophenyl)-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid hydrochloride
• Synonyms: 6-fluoro-1-(4-fluorophenyl)-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid hydrochloride; Sarafloxacin HCl; Sarafloxacin Hydrochloride; 6-Fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic Acid Hydrochloride; A 56620; PD 121960; Sarafin; Sarafloxacin Hydrochloride

Database IDs

• CAS Number: 91296-87-6
• PubChem SID: 162216953
• PubChem CID: 56207

CALCULATED PROPERTIES

• Acid pKa: 5.7395115
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.24145465
• LogD (pH = 7.4): 0.56401366
• Log P: 0.56443995
• Molar Refractivity: 99.8989 cm^3
• Polarizability: 36.74501 Å^3
• Polar Surface Area: 72.88 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Sparingly Soluble in DMSO and Water
• Apperance: Pale Yellow Solid
• Melting Point: >240°C (dec.)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

Pharmacology Properties

• Target: Others
• Mechanism of Action: DNA gyrase inhibitor

Product Information

• Salt Data: HCl
• Application(s): Antibacterial agent

DETAILS

Toronto Research Chemicals - S139500

Sarafloxacin is a fluorinated quinolone antibacterial.

REFERENCES

• Digranes, A., et al.: Chemotherapy, 34, 298 (1986)
• Fernandes, P.B., et al.: Antimicrob. Ag. Chemother., 29, 201 (1986)
• Chu, D.T. et al., J. Med. Chem., 1985, 28, 1558, (synth)
• Fernandes, P.B. et al., Antimicrob. Agents Chemother., 1986, 29, 201, (activity)
• Granneman, G.R. et al., J. Chromatogr., 1987, 413, 199, (hplc)
• Fernandes, C.J. et al., Chemotherapy (Basel), 1988, 34, 216, (activity)
• Bouzard, D. et al., J. Med. Chem., 1989, 32, 537, (activity)
• Xiao, W. et al., J. Pharm. Sci., 1989, 78, 585, (synth, pharmacol)
• Bauer, J.F. et al., Pharm. Res., 1990, 7, 1177, (hplc)