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Issue 11, 2010
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Incorporating active pharmaceutical ingredients into a molecular salt using a chiral counterion

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Abstract

The molecular salt structures of three active pharmaceutical ingredients with the pure enantiomers of the amine 1-phenylethylamine contain a predictable hydrogen bonded heterosynthon. The APIs containing a carboxylic acid functional group, namely (S)-ibuprofen, diclofenac and niflumic acid, transfer their acid proton to the amine and form three charge-assisted N+HO hydrogen bonds. These three hydrogen bonds form hydrogen bonded columns with repeating R34(10) rings. The formation of the heterosynthon is predicted from a Cambridge Structural Database search, where the heterosynthon is formed in 87% of the structures containing carboxylate and ammonium functional groups, even in the presence of other hydrogen bonding functional groups such as alcohols.

Graphical abstract: Incorporating active pharmaceutical ingredients into a molecular salt using a chiral counterion

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Supplementary files

Article information


Submitted
29 Mar 2010
Accepted
04 Jun 2010
First published
06 Jul 2010

CrystEngComm, 2010,12, 3634-3641
Article type
Paper

Incorporating active pharmaceutical ingredients into a molecular salt using a chiral counterion

A. Lemmerer, S. A. Bourne, M. R. Caira, J. Cotton, U. Hendricks, L. C. Peinke and L. Trollope, CrystEngComm, 2010, 12, 3634
DOI: 10.1039/C0CE00043D

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