Chloramphenicol Palmitate

• CAT Number: R023220
• CAS Number: 530-43-8
• Molecular Formula: C27H42Cl2N2O6
• Molecular Weight: 561.541
• Purity: ≥95%
• Synonyms: (2R,3R)-2-[(Dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl Ester Hexadecanoic Acid; [R-(R*,R*)]-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl Ester Hexadecanoic Acid; Palmitic acid Ester with Chloramphenicol; Palmitic Acid α-e
• Storage: -20°C
• IUPAC Name: [(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] hexadecanoate
• InChI: InChI=1S/C27H42Cl2N2O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-24(32)37-20-23(30-27(34)26(28)29)25(33)21-16-18-22(19-17-21)31(35)36/h16-19,23,25-26,33H,2-15,20H2,1H3,(H,30,34)/t23-,25-/m1/s1
• InChIKey: PXKHGMGELZGJQE-ILBGXUMGSA-N
• SMILES: CCCCCCCCCCCCCCCC(=O)OCC(C(C1=CC=C(C=C1)[N+](=O)[O-])O)NC(=O)C(Cl)Cl

Chloramphenicol 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.After entering a bacterial cell, chloramphenicol binds to the 50S ribosomal subunit preventing peptide bond formation. Resistance to chloramphenicol may be due to decreased cell permeability or a mutation in the 50S ribosomal subunit.

Reference

The structure of chloramphenicol palmitate. Edgerton W.H. et al. J. Am. Chem. Soc. 1955, 77, 27.