Evaluatin The Effect of Primary Amine in Bitterness of Selected Cephalosporins
DOI:
https://doi.org/10.25156/ptj.v13i1.1357Keywords:
Cephalexin, Cefaclor, bitterness, primary amine, Schiff base.Abstract
Abstract
Background and objective:
Cephalosporins, particularly Cephalexin and Cefaclor, are widely prescribed antibiotics known for their characteristic bitter taste, which poses challenges to their palatability and patient compliance. This bitterness is attributed to the specific chemical composition of these substances. The sensory experience of bitterness is influenced by distinct functional groups present in various foods and chemicals, along with the primary amine functional group being identified as a significant contributor to bitterness in compounds such as Cephalosporins.
The prevalence of primary amine-related bitterness in both foods and medicines, including Cephalosporins, underscores the need to address this aversion factor. To overcome this taste challenge, researchers have developed diverse techniques and strategies to modify these antibiotics' chemical structure while preserving their therapeutic efficacy.
In line with this objective, the current study endeavours to delve deeper into the role played by the primary amine functional group in generating the bitter taste associated with Cephalexin and Cefaclor. By doing so, this investigation aims to provide valuable insights that contribute to the optimization of future antibiotic formulations. The outcomes of this study have the potential to advance the development of antibiotics with enhanced palatability, fostering improved patient acceptance and adherence to treatment regimens.
Results: The formation of imines on the primary amine functional group in both Cephalexin and Cefaclor was achieved through the creation of Schiff bases with aldehydes, specifically Citral, Vanillin, and benzaldehyde. This chemical transformation led to a slight alteration in the bitterness intensity measurements. From this, it can be deduced that the primary amine groups in Cephalexin and Cefaclor significantly conferred bitterness to these medications.
Interestingly, a more pronounced reduction in bitterness was observed in the Cephalexin-Aldehyde complex compared to the same complex of Cefaclor. However, despite these changes, the modified complexes were still not transformed into palatable prodrugs of the respective cephalosporins. This observation suggests that while the primary amine groups are contributors to bitterness, they are not the sole determinants. Bitterness in Cephalexin and Cefaclor is likely influenced by multiple functional groups beyond primary amines. Therefore, the outcomes imply that addressing the primary amine alone, through chemical modifications, is insufficient to overcome the bitterness associated with these cephalosporins.
In conclusion, the established bitterness in Cephalexin and Cefaclor involves more than just their primary amine functional groups. While efforts were made to mitigate bitterness through chemical modifications, focusing solely on masking the primary amine does not appear effective for overcoming the bitterness of these cephalosporins— at least in the case of Cephalexin and Cefaclor.
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