1-[(2,2,3,3-2H4)cyclopropyl]-8-(difluoromethoxy)-7-[(1R)-1-methyl-2,3-dihydro-1H-isoindol-5-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 169580
• Molecular Formular: C23H20F2N2O4
• Molecular Mass: 426.4127064
• Monoisotopic Mass: 426.13911357
• SMILES: c12c(c(=O)c(cn1C1CC1)C(=O)O)ccc(c2OC(F)F)c1ccc2c(c1)CN[C@@H]2C
• Canonical SMILES: FC(Oc1c(ccc2c1n(cc(c2=O)C(=O)O)C1CC1)c1ccc2c(c1)CN[C@@H]2C)F
• InChI: InChI=1S/C23H20F2N2O4/c1-11-15-5-2-12(8-13(15)9-26-11)16-6-7-17-19(21(16)31-23(24)25)27(14-3-4-14)10-18(20(17)28)22(29)30/h2,5-8,10-11,14,23,26H,3-4,9H2,1H3,(H,29,30)/t11-/m1/s1
• InChIKey: NJDRXTDGYFKORP-LLVKDONJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2,2,3,3-^2H₄)cyclopropyl]-8-(difluoromethoxy)-7-[(1R)-1-methyl-2,3-dihydro-1H-isoindol-5-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: 1-[(2,2,3,3-^2H₄)cyclopropyl]-8-(difluoromethoxy)-7-[(1R)-1-methyl-2,3-dihydro-1H-isoindol-5-yl]-4-oxoquinoline-3-carboxylic acid
• Synonyms: 1-(Cyclopropyl-d4)-8-(difluoromethoxy)-7-[(1R)-2,3-dihydro-1-methyl-1H-isoindol-5-yl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid; (+)-; Ganefloxacin-d4; T 3811-d4; Garenoxacin-d4

Database IDs

• PubChem SID: 162263712
• PubChem CID: 57369499

CALCULATED PROPERTIES

• Acid pKa: 6.0508494
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.086272
• LogD (pH = 7.4): 1.5377023
• Log P: 1.5394918
• Molar Refractivity: 110.3687 cm^3
• Polarizability: 42.42764 Å^3
• Polar Surface Area: 78.87 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G245502

Labelled Garenoxacin. Des-F(6)-quinolone antibacterial; topoisomerase II inhibitor. Antibacterial.

REFERENCES

• Hayashi, K., et al.: Arzneim.-Forsch., 52, 903 (2002)
• Ince, D., et al.: Antimicrob. Agents Chemother., 46, 3370 (2002)
• Nagai, A., et al.: J. Toxicol. Sci., 27, 219 (2002)