7-[(4Z)-3-[amino(2H2)methyl]-4-(methoxymethylidene)(4,5-13C2)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

• ChemBase ID: 169602
• Molecular Formular: C19H21FN4O4
• Molecular Mass: 390.37815288
• Monoisotopic Mass: 390.16139307
• SMILES: c1(c(cc2c(n1)n(cc(c2=O)C(=O)O)C1CC1)F)N1CC(/[13C](=C/OC)/[13CH2]1)CN
• Canonical SMILES: CO/C=[13C]/1\[13CH2]N(CC1CN)c1nc2c(cc1F)c(=O)c(cn2C1CC1)C(=O)O
• InChI: InChI=1S/C19H21FN4O4/c1-28-9-11-7-23(6-10(11)5-21)18-15(20)4-13-16(25)14(19(26)27)8-24(12-2-3-12)17(13)22-18/h4,8-10,12H,2-3,5-7,21H2,1H3,(H,26,27)/b11-9+/i7+1,11+1
• InChIKey: SWHSFCVCXGGXHA-ANCNLOPZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(4Z)-3-[amino(^2H₂)methyl]-4-(methoxymethylidene)(4,5-^1^3C₂)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
• IUPAC Traditional name: 7-[(4Z)-3-[amino(^2H₂)methyl]-4-(methoxymethylidene)(4,5-^1^3C₂)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid
• Synonyms: 7-[3-(Aminomethyl)-4-(methoxyimino)-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid-13C2,d2; SB-265805-13C2,d2; LB-20304-13C2,d2; Gemifloxacin-13C2,d2

Database IDs

• PubChem SID: 162263734
• PubChem CID: 71317057

CALCULATED PROPERTIES

• Acid pKa: 5.533592
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.555062
• LogD (pH = 7.4): -1.3159957
• Log P: -1.3202801
• Molar Refractivity: 102.0551 cm^3
• Polarizability: 37.393394 Å^3
• Polar Surface Area: 108.99 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Off-White Amorphous Solid
• Melting Point: 235-237°C

DETAILS

Toronto Research Chemicals - G336002

Third generation fluorinated quinolone antibacterial.

REFERENCES

• Wise, R., et al.: J. Antimicrob. Chemother., 44, 679 (1999)
• Allen, A., et al.: Antimicrob. Agents Chemother., 44, 1604 (1999)
• Blondeau, B., et al.: Expert Opin. Pharmacother., 5, 1117 (2004)