Salts of the anti-HIV drug lamivudine with phthalic and salicylic acids


Autoria(s): da Silva, Cameron Capeletti; Coelho, Renan Rezende; Cirqueira, Marilia de Lima; Campos de Melo, Ariane Carla; Landre Rosa, Iara Maria; Ellena, Javier; Martins, Felipe Terra
Contribuinte(s)

UNIVERSIDADE DE SÃO PAULO

Data(s)

06/11/2013

06/11/2013

2012

Resumo

Salts of the anti-HIV drug lamivudine, with phthalic acid and salicylic acid as counterions, were investigated in this study. Neither the packing of the (lamivudine)(+)(phthalic acid)(-) ion pairs nor the conformation of the lamivudine moiety itself were similar to those found in other multicomponent molecular salts of the drug, such as hydrogen maleate and saccharinate ones, even though all three salts crystallize in the same P2(1)2(1)2(1) orthorhombic space group with similar unit cell metrics. Lamivudine salicylate assumes a different crystal structure to those of the hydrogen maleate and saccharinate salts, crystallizing in the P2(1) monoclinic space group as a monohydrate whose (lamivudine)(+)(salicylic acid)(-) ion pair is assembled through two hydrogen bonds with cytosine as a dual donor to both oxygens of the carboxylate, such as in the pairing of lamivudine with a phthalic acid counterion. In lamivudine salicylate monohydrate, the drug conformation is related to the hydrogen maleate and saccharinate salts. However, such a conformational similarity is not related to the intermolecular interaction patterns. Lamivudine and water molecules alternate into helical chains in the salicylate salt monohydrate.

Brazilian Research Council CNPq (Conselho Nacional de Desenvolvimento Cientifico e Tecnologico)

Brazilian Research Council CNPq (Conselho Nacional de Desenvolvimento Cientifico e Tecnologico) [472623/2011-7 - Universal 14/2011]

Identificador

CRYSTENGCOMM, CAMBRIDGE, v. 14, n. 14, supl. 1, Part 3, pp. 4562-4566, NOV, 2012

1466-8033

http://www.producao.usp.br/handle/BDPI/42011

10.1039/c2ce25386k

http://dx.doi.org/10.1039/c2ce25386k

Idioma(s)

eng

Publicador

ROYAL SOC CHEMISTRY

CAMBRIDGE

Relação

CRYSTENGCOMM

Direitos

openAccess

Copyright ROYAL SOC CHEMISTRY

Palavras-Chave #ACTIVE PHARMACEUTICAL INGREDIENTS #CO-CRYSTALS #CRYSTALLIZATION #POLYMORPHISM #COCRYSTALS #WATER #CHEMISTRY, MULTIDISCIPLINARY #CRYSTALLOGRAPHY
Tipo

article

original article

publishedVersion