ArticleIUCrJ2024
The role of alkyl chain length in the melt and solution crystallization of paliperidone aliphatic prodrugs.
Article in IUCrJ, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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Who cites it
2 citing papers in PubMed.
- Effect of Alkyl Chain Length on Physicochemical and Pharmacokinetic Performance of Aripiprazole Fatty Acid Prodrugs for Long-Acting Injectable Suspensions.Pharmaceutics · 2026Article
- The synthesis of indomethacin prodrugs for the formation of nanosuspensions by emulsion templated freeze drying.RSC advances · 2025Article
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Authors and funding
6 authors.
Funding
Abstract
Fatty acid-derivative prodrugs have been utilized extensively to improve the physicochemical, biopharmaceutical and pharmacokinetic properties of active pharmaceutical ingredients. However, to our knowledge, the crystallization behavior of prodrugs modified with different fatty acids has not been explored. In the present work, a series of paliperidone aliphatic prodrugs with alkyl chain lengths ranging from C4 to C16 was investigated with respect to crystal structure, crystal morphology and crystallization kinetics. The paliperidone derivatives exhibited isostructural crystal packing, despite the different alkyl chain lengths, and crystallized with the dominant (100) face in both melt and solution. The rate of crystallization for paliperidone derivatives in the melt increases with alkyl chain length owing to greater molecular mobility. In contrast, the longer chains prolong the nucleation induction time and reduce the crystal growth kinetics in solution. The results show a correlation between difficulty of nucleation in solution and the interfacial energy. This work provides insight into the crystallization behavior of paliperidone aliphatic prodrugs and reveals that the role of alkyl chain length in the crystallization behavior has a strong dependence on the crystallization method.
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