6-fluoro-1-methyl-7-{4-[(5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl](2H8)piperazin-1-yl}-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid

• ChemBase ID: 177081
• Molecular Formular: C21H20FN3O6S
• Molecular Mass: 461.4634032
• Monoisotopic Mass: 461.1056846
• SMILES: n12c(c(c(=O)c3c1cc(c(c3)F)N1CCN(CC1)Cc1oc(=O)oc1C)C(=O)O)SC2C
• Canonical SMILES: O=c1oc(c(o1)CN1CCN(CC1)c1cc2c(cc1F)c(=O)c(c1n2C(C)S1)C(=O)O)C
• InChI: InChI=1S/C21H20FN3O6S/c1-10-16(31-21(29)30-10)9-23-3-5-24(6-4-23)15-8-14-12(7-13(15)22)18(26)17(20(27)28)19-25(14)11(2)32-19/h7-8,11H,3-6,9H2,1-2H3,(H,27,28)
• InChIKey: PWNMXPDKBYZCOO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-fluoro-1-methyl-7-{4-[(5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl](^2H₈)piperazin-1-yl}-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid
• IUPAC Traditional name: 6-fluoro-1-methyl-7-{4-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl](^2H₈)piperazin-1-yl}-4-oxo-1H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid
• Synonyms: 6-Fluoro-1-methyl-7-[4-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]-1-(piperazinyl-d8)]-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic Acid; NM 441-d8; Quisnon-d8; Sword-d8; Prulifloxacin-d8

Database IDs

• PubChem SID: 164232991
• PubChem CID: 71751862

CALCULATED PROPERTIES

• Acid pKa: 5.9755955
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 2.6894138
• LogD (pH = 7.4): 1.428254
• Log P: 2.6541631
• Molar Refractivity: 127.3688 cm^3
• Polarizability: 43.321873 Å^3
• Polar Surface Area: 99.62 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P838887

Labelled Fluoroquinoline antibacterial; prodrug for active metabolite, Ulifloxacin. Antibacterial.

REFERENCES

• Ozaki, M., et al.: Antimicrob. Agents Chemother., 35, 2496 (1991)
• Segawa, J., et al.: J. Med. Chem., 35, 4727 (1991)
• Nakashima, M., et al.: J. Clin. Pharmacol., 34, 930 (1991)