Chloramphenicol succinate

• CAT Number: R001507
• CAS Number: 3544-94-3
• PubChem Substance ID: 656580
• Molecular Formula: C15H16Cl2N2O8
• Molecular Weight: 423.2
• Purity: 99%
• Appearance: White solid
• Storage: -20°C
• Analysis method: HPLC
• IUPAC Name: 4-[(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propoxy]-4-oxobutanoic acid
• InChI: InChI=1S/C15H16Cl2N2O8/c16-14(17)15(24)18-10(7-27-12(22)6-5-11(20)21)13(23)8-1-3-9(4-2-8)19(25)26/h1-4,10,13-14,23H,5-7H2,(H,18,24)(H,20,21)/t10-,13-/m1/s1
• InChIKey: LIRCDOVJWUGTMW-ZWNOBZJWSA-N
• SMILES: C1=CC(=CC=C1C(C(COC(=O)CCC(=O)O)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]

Chloramphenicol succinate is prepared by acylation of chloramphenicol with succinic anhydride to provide a water soluble pro-drug. Chloramphenicol succinate represents an alternative pro-drug strategy for chloramphenicol that has found a niche in surface antibiotic treatment in surgery. Chloramphenicol succinate is significantly less active than chloramphenicol but acts as a prodrug, forming chloramphenicol in the presence of succinate dehydrogenase.
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

Chloramphenicol succinate, a competitive substrate and inhibitor of succinate dehydrogenase: possible reason for its toxicity. Ambekar C.S. et al. Toxicology in vitro 2004, 18, 441.