7-[(4Z)-3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

• ChemBase ID: 169601
• Molecular Formular: C18H20FN5O4
• Molecular Mass: 389.3809032
• Monoisotopic Mass: 389.14993237
• SMILES: c1(c(cc2c(n1)n(cc(c2=O)C(=O)O)C1CC1)F)N1CC(/C(=N/OC)/C1)CN
• Canonical SMILES: NCC1CN(C/C/1=N\OC)c1nc2c(cc1F)c(=O)c(cn2C1CC1)C(=O)O
• InChI: InChI=1S/C18H20FN5O4/c1-28-22-14-8-23(6-9(14)5-20)17-13(19)4-11-15(25)12(18(26)27)7-24(10-2-3-10)16(11)21-17/h4,7,9-10H,2-3,5-6,8,20H2,1H3,(H,26,27)/b22-14+
• InChIKey: ZRCVYEYHRGVLOC-HYARGMPZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(4Z)-3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
• IUPAC Traditional name: gemifloxacin
• Synonyms: 7-[3-(Aminomethyl)-4-(methoxyimino)-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid Mesilate; SB-265805 Mesilate; LB-20304 Mesilate; Gemifloxacin Mesilate; (Z)-7-(3-(AMinoMethyl)-4-(MethoxyiMino)pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Database IDs

• CAS Number: 175463-14-6; 210353-53-0
• PubChem SID: 162263733
• PubChem CID: 9571107

CALCULATED PROPERTIES

• Acid pKa: 5.5331783
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -1.1519698
• LogD (pH = 7.4): -0.91324586
• Log P: -0.91842437
• Molar Refractivity: 99.7408 cm^3
• Polarizability: 36.575836 Å^3
• Polar Surface Area: 121.35 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Methanol (hot); Water
• Apperance: Beige Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

Product Information

• Purity: 97%

DETAILS

Toronto Research Chemicals - G336000

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)