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Chloramphenicol palmitate

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Chloramphenicol palmitate Basic information
Chloramphenicol palmitate Chemical Properties
  • Melting point:90 C
  • alpha D26 +24.6° (c = 5 in ethanol)
  • Boiling point:691.6±55.0 °C(Predicted)
  • Density 1.2354 (rough estimate)
  • refractive index 1.7350 (estimate)
  • storage temp. Store at RT.
  • pka10.69±0.46(Predicted)
  • form neat
  • Water Solubility 8.423ug/L(25 ºC)
  • λmax271nm(EtOH)(lit.)
  • Merck 14,2077
  • BRN 2826438
  • CAS DataBase Reference530-43-8(CAS DataBase Reference)
Safety Information
Chloramphenicol palmitate Usage And Synthesis
  • Chemical Propertieswhite crystals
  • OriginatorChloromycetin,Parke Davis,US,1951
  • Usesantibacterial, antirickettsial
  • UsesChloramphenicol palmitate is prepared by acylation of chloramphenicol with palmitic acid. Although chloramphenicol palmitate is a more hydrophobic drug which should enhance bioavailability, the primary advantage of the ester is to mask the taste of chloramphenicol in oral formulations. Chloramphenicol palmitate is significantly less active than chloramphenicol but acts as a prodrug, being readily hydrolysed by acid and esterase in the gut to release chloramphenicol.
  • Manufacturing Process1,674 g of palmitoyl chloride is added to 1,870 g of D(-)-threo-1-pnitrophenyl-2-dichloroacetamidopropane-1,3-diol (chloramphenicol) in 2,700 cc of pyridine and the solution stirred for 1 hour. The mixture is poured into 16 liters of water and the solid collected. Recrystallization of the crude product from benzene yields the desired D(+)-threo-1-p-nitrophenyl- 1dichloroacetamido-3-palmitoyloxypropane-1-ol in pure form: MP 90°C.
  • brand nameChloromycetin Palmitate (Parke- Davis).
  • Therapeutic FunctionAntibacterial; Antirickettsial
  • General DescriptionChloramphenicol palmitate is the palmitic acid ester ofchloramphenicol. It is a tasteless prodrug of chloramphenicolintended for pediatric use. The ester must hydrolyze invivo following oral absorption to provide the active form.Erratic serum levels were associated with early formulationsof the palmitate, but the manufacturer claims that thebioavailability of the current preparation is comparable tothat of chloramphenicol itself.
  • Safety ProfileModerately toxic by oral route. An experimental teratogen. Other experimental reproductive effects. An antibiotic. When heated to decomposition it emits very toxic fumes of NOx and Cl-. See also other chloramphenicol entries.
  • Purification MethodsThe palmitate crystallises from *benzene or xylene with m 105-106o and [] D –39.5o (c 2, Et2O), max 267.3nm. [Edgerton et al. J Am Chem Soc 77 27 1955, Beilstein 13 IV 2753.]
Chloramphenicol palmitate Preparation Products And Raw materials
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