| Identification | More | [Name]
Grepafloxacin | [CAS]
119914-60-2 | [Synonyms]
GREPAFLOXACIN
GREPAFLOXACIN HYDROCHLORIDE
1-Cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | [EINECS(EC#)]
631-454-3 | [Molecular Formula]
C19H22FN3O3 | [MDL Number]
MFCD00865116 | [Molecular Weight]
359.39 | [MOL File]
119914-60-2.mol |
| Questions And Answer | Back Directory | [Synthesis]
1-Bromo-2,4,5-trifluoro-3-(trimethylsilyl)benzene (i) and methyl trifluoromethanesulfonate (ii) dissolved in THF react under butyllithium and diisopropylethylamine conditions to give 2-bromo-3,5,6-trifluoro-4-(trimethylsilane)toluene (iii). Passing through butyllithium and carbon dioxide yields 2,4,5-trifluoro-6-methyl-3-(trimethylsilyl)benzoic acid (iv), which reacts in acetonitrile and CSF to give the corresponding benzoic acid (v). This benzoic acid then reacts with monoethyl malonate and... The reaction of oxaloyl chloride and butyllithium yields ethyl 3-(3,4,6-trifluoro-2-methylphenyl)-2-oxopropionate (Vii), which is then condensed with triethyl acetic anhydride orthoformate to form an ethoxylated derivative (VIII). This derivative then undergoes a cyclization reaction with cyclopropylamine to give ethyl 1-cyclopropyl-6,7-difluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (x), which is hydrolyzed to give the corresponding free acid (Xi). Finally, this compound is condensed with 2-methylpiperazine (Xii) to give the final product, Grepafloxacin.
Figure 1 shows the synthetic route of Grepafloxacin. |
| Chemical Properties | Back Directory | [Melting point ]
189-192 ºC | [Boiling point ]
610.0±55.0 °C(Predicted) | [density ]
1.366 | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
6.44±0.50(Predicted) | [color ]
Pale Beige to Pale Yellow | [Stability:]
Hygroscopic | [CAS DataBase Reference]
119914-60-2(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
dl-Grepafloxacin is an antibacterial compound used to treat various respirator infections. | [Definition]
ChEBI: Grepafloxacin is a member of quinolines, a quinolone antibiotic and a fluoroquinolone antibiotic. | [in vivo]
Grepafloxacin (OPC-17116; 200 mg/kg; p.o.; Balb/c mice) displays good safety profile in terms of phototoxicity[2].
Grepafloxacin (25-200 mg/kg; p.o.; 5 days/week for 4 weeks; female C57BL6/J-Lyst bg-J/ mice/beige mice) has modest activities in both intranasal (IN) infection and intravenous (IV) Mycobacterium aviuminfection models[3]. | Animal Model: | Female Balb/c mice (5-6 weeks)[2] | | Dosage: | 200 mg/kg | | Administration: | Oral administration; once | | Result: | Had mild and short-lived erythema and no changed auricular thickness. |
| Animal Model: | Female C57BL6/J-Lyst bg-J/ mice/beige mice with mycobacterium avium infection[3] | | Dosage: | 25, 50, 100, and 200 mg/kg | | Administration: | Oral administration; 5 days/week for 4 weeks | | Result: | Had bactericidal activity and limited the growth of the bacteria. |
| [IC 50]
Quinolone |
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