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Issue 13, 2011
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Drug-drug co-crystals: Temperature-dependent proton mobility in the molecular complex of isoniazid with 4-aminosalicylic acid

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Abstract

Two drug-drug co-crystals of the anti-tuberculosis drugs isoniazid (INH), pyrazinamide (PYR) and 4-aminosalicylic acid (PAS) are reported. The first is the 1 : 1 molecular complex of INH and PAS. The second is the monohydrate of the 1 : 1 complex of PYR and PAS. The crystal structures of both co-crystals are characterized by a number of hydrogen bonded synthons. Hydrogen bonding of the COOH⋯Npyridine type is found in both cases. In the INH : PAS co-crystal, there are two symmetry independent COOH⋯Npyridine hydrogen bonds. In one of these, the H-atom is located on the carboxylic group and is indicative of a co-crystal. In the second case, partial proton transfer occurs across the hydrogen bond, and the extent of proton transfer depends on the temperature. This is more indicative of a salt. Drug-drug co-crystals may have some bearing in the treatment of tuberculosis.

Graphical abstract: Drug-drug co-crystals: Temperature-dependent proton mobility in the molecular complex of isoniazid with 4-aminosalicylic acid

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Article information


Submitted
11 Nov 2010
Accepted
21 Dec 2010
First published
25 Feb 2011

CrystEngComm, 2011,13, 4358-4364
Article type
Paper

Drug-drug co-crystals: Temperature-dependent proton mobility in the molecular complex of isoniazid with 4-aminosalicylic acid

P. Grobelny, A. Mukherjee and G. R. Desiraju, CrystEngComm, 2011, 13, 4358
DOI: 10.1039/C0CE00842G

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