Issue 35, 2014

Structural insight into cocrystallization with zwitterionic co-formers: cocrystals of S-naproxen

Abstract

The screening of S-naproxen, S-oxiracetam, S-diprophylline, and levetiracetam with a series of essential and nonessential amino acid co-formers has yielded cocrystals only for S-naproxen, thus showing that amino acids seem to have a preference for forming cocrystals with compounds containing a carboxyl group. Herein, we report the crystal structures of four S-naproxen cocrystals: S-naproxen/L-alanine, S-naproxen/D-alanine, S-naproxen/D-tyrosine, and S-naproxen/D-tryptophan monohydrate. All of the described cocrystals show similar structural motifs, i.e., amino acids form head-to-tail chains with strong charge-assisted hydrogen bonding, which are similar to those found in the individual amino acids, with S-naproxen molecules grafted on them. According to the systematic search of the Cambridge Structural Database for other cocrystals that involve zwitterionic co-formers, charge-assisted hydrogen bonds between amino acid molecules play an essential role, being present in the majority of structures. The results of this work provide an insight into structural aspects of cocrystallization with zwitterionic co-formers, offer new possibilities for S-naproxen pharmaceutical formulations, and can serve as guidelines when developing new cocrystals involving zwitterionic co-formers.

Graphical abstract: Structural insight into cocrystallization with zwitterionic co-formers: cocrystals of S-naproxen

Supplementary files

Article information

Article type
Paper
Submitted
18 fev 2014
Accepted
03 apr 2014
First published
13 may 2014

CrystEngComm, 2014,16, 8185-8196

Structural insight into cocrystallization with zwitterionic co-formers: cocrystals of S-naproxen

N. Tumanova, N. Tumanov, K. Robeyns, Y. Filinchuk, J. Wouters and T. Leyssens, CrystEngComm, 2014, 16, 8185 DOI: 10.1039/C4CE00353E

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