Diversity in Single- and Multiple-Component Crystals. The Search for and Prevalence of Polymorphs and Cocrystals

Stahly, G. Patrick

doi:10.1021/cg060838j

Cited by 489 publications

(355 citation statements)

References 105 publications

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“…Consequently, drug bioavailability may be improved by the preparation of lower melting point polymorphs, co-crystals, solvates of the drug (Stahly, 2007) or alternatively by preparing a more soluble salt form (Berge et al, 1977).…”

Section: Introductionmentioning

confidence: 99%

Preparation and solid state characterisation of chlorothiazide sodium intermolecular self-assembly suprastructure

Paluch

Tajber

McCabe

et al. 2010

European Journal of Pharmaceutical Sciences

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Please cite this article as: Paluch, K.J., Tajber, L., McCabe, T., O'Brien, J.E., Corrigan, O.I., Healy, A.M., Preparation and solid state characterisation of chlorothiazide sodium intermolecular self assembly suprastructure, European Journal of Pharmaceutical Sciences (2010Sciences ( ), doi:10.1016Sciences ( /j.ejps.2010 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Page 1 of 36A c c e p t e d M a n u s c r i p t A c c e p t e d M a n u s c r i p t 2 Abstract Chlorothiazide (CTZ), unlike other thiazide diuretics, can form salts. An injectable formulation containing the sodium salt is available; however neither the physicochemical characteristics of the salt nor its solid state form have been previously reported. This work reports on the crystal structure of chlorothiazide sodium. The structure was investigated by single crystal X-ray and nuclear magnetic spectroscopy (NMR) analyses and compared to chlorothiazide, while the solid state characteristics were assessed by thermal analysis, powder X-ray diffraction, infrared spectroscopy, dynamic moisture sorption and solubility analysis. The crystal structure of chlorothiazide sodium was determined to be triclinic; the crystal space group type was P-1. Chlorothiazide sodium presented a self-assembly polymeric-type suprastucture, where the unit cell comprised two chlorothiazide molecules bonded together with sodium cations through the water bridges. The coordinate centre comprised the following:The crystalline material was determined to be a monosodium dihydrate, stable in the range of 10-90% relative humidity (RH) at 25 ˚C. Additional processing of the salt resulted in a crystalline anhydrous form which was stable in the range 0-20% RH at 25 ˚C. The aqueous solubility of the chlorothiazide sodium dihydrate at 37 °C was found to be approximately 400-fold higher than that of chlorothiazide, which may present biopharmaceutical advantages for the salt compared to the non-salt form.

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Section: Introductionmentioning

confidence: 99%

Preparation and solid state characterisation of chlorothiazide sodium intermolecular self-assembly suprastructure

Paluch

Tajber

McCabe

et al. 2010

European Journal of Pharmaceutical Sciences

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“…as used by Stahly [10] ): as the solid which consists of two or more components that form a unique crystalline structure having unique properties.…”

Section: Introductionmentioning

confidence: 99%

Even–odd effect in the co-crystals of pyrazine and dicarboxylic acids

Dutkiewicz

Kubicki

2014

Struct Chem

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The co-crystals of pyrazine with dicarboxylic acids of the form (COOH)-(CH 2 ) n -COOH: oxalic (n = 0), malonic (n = 1) succinic (n = 2), glutaric (n = 3), adipic (n = 4), and pimelic (n = 5) acid, were synthesized and structurally characterized by means of X-ray diffraction. There are two principal structural motifs, depending on the stoichiometry: for 1:1 co-crystals, there are chains of alternate pyrazine and acid molecules, connected by strong O-HÁÁÁN hydrogen bonds (ÁÁÁpyrÁÁÁacidÁÁÁpyrÁÁÁacidÁÁÁ) while for 2:1 stoichiometry the chains are made of pyrazine molecules and carboxylic acid centrosymmetric dimers (ÁÁÁpyrÁÁÁacidÁÁÁacidÁÁÁpyrÁÁÁ). The first possibility is observed for all acids in the series, while the second one only for these with odd numbers of methylene groups. The geometrical features of the acids do not show the clear indication for a reason of such behavior, the most probable reason can be connected with the possible symmetry of the acid molecule, C i for n even, and with the mutual orientation of terminal carbonyl and hydroxyl groups, defined by improper O=CÁÁÁC=O torsion angles, which are close to 180°for even and have much smaller values for odd n values.

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“…Contudo, adotar-se-ão as seguintes definições: [3][4][5] Complexos moleculares: quando a molécula agregada a um API é utilizada com o intuito de promover a interação entre as demais moléculas de API no cristal.…”

Section: Formas Cristalinas De Compostos Farmacêuticosunclassified

“…3 O polimorfismo conformacional é aquele no qual moléculas conformacionalmente flexíveis podem se contorcer em formas capazes de empacotarem-se em diferentes estruturas tridimensionais. 11 Um exemplo desse tipo de polimorfismo é o apresentado pelo composto 5-metil-2-[(2-nitrofenil)amino]-3-tiofeno carbonitrila (Figura 1.2), também conhecido como ROY (do inglês Red Orange Yellow).…”

Section: Formas Cristalinas De Compostos Farmacêuticosunclassified

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Caracterização de estado sólido de insumos farmacêuticos ativos: clorpropamida, nevirapina e dietilcarbamazina

Silva¹

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Dedico esta dissertação aos meus pais Alcir e Marta e ao meu marido Elvis, com amor, carinho e gratidão por todo o encorajamento, compreensão e apoio incondicional. AGRADECIMENTOS-A Deus, por me sustentar em todo o tempo, me capacitar, me confortar e me reanimar nos momentos em que pensava já não ser mais capaz de continuar.-Aos meus pais, Alcir Militão da Silva e Marta Íris Pinheiro Militão da Silva, pelo amor, auxílio emocional e incentivo, incondicionais.-Ao meu marido Elvis Donizeti Neves, por me alavancar nos momentos mais difíceis, por exigir sempre o meu melhor e por me mostrar como tirar grandes lições a partir de nossos erros. À minha sogra Yuri e minha cunhada Letícia pelo apoio e incentivo sempre.-Ao Prof.º Dr. Javier A. Ellena, por compartilhar comigo sua magnífica experiência e conhecimento, pela orientação e confiança, pelo constante apoio, pela paciência e carinho, pelas brigas e discussões, por acreditar na minha capacidade mesmo quando eu já não acreditava mais e, sobretudo, pela sua amizade e a de sua família.-Ao Prof.º Dr. Alejandro Pedro Ayala (Universidade Federal do Ceará), à Prof.ª Dra. Sílvia Cuffini (Agência Córdoba Ciencia-Unidad CEPROCOR) e ao grupo de pesquisa da Dra. Núbia Boechat (Instituto de Tecnologia em Fármacos -Farmanguinhos), por colaborarem e fornecerem as amostras analisadas nesta dissertação.-Aos profs. Drs. Eduardo Castellano e Yvone Mascarenhas por dedicarem tempo às minhas dúvidas e me auxiliarem na compreensão de alguns resultados.-Ao pessoal da sala 25: Alexandre Araújo, Jahyr Theodoro, Rodrigo Corrêa, Felipe Martins, Leandro Ribeiro, Marcelo de Andrade, Karina de Paula e Márcio D.Bocelli por todo o incentivo moral, pelas brincadeiras, piadas, pelo cafezinho e pela ajuda nos trabalhos. Porém, não podia deixar de ressaltar que -vocês não valem nada!‖ -Aos colegas e funcionários do Grupo de Cristalografia do IFSC.-E a todos meus amigos e amigas que colaboraram para a realização deste projeto, direta ou indiretamente. "Era uma vez um escritor que morava em uma tranqüila praia, junto de uma colônia de pescadores. Todas as manhãs ele caminhava à beira do mar para se inspirar, e à tarde ficava em casa escrevendo.Certo dia, caminhando na praia, ele viu um vulto que parecia dançar. Ao chegar perto, ele reparou que se tratava de um jovem que recolhia estrelas-do-mar da areia para, uma por uma, jogá-las novamente de volta ao oceano.- "Por que está fazendo isso?"-perguntou o escritor -"Você não vê! --explicou o jovem--A maré está baixa e o sol está brilhando. Elas irão secar e morrer se ficarem aqui na areia".O escritor espantou-se. One of the main goals of the pharmaceutical industry is to plan, synthesize and characterize chemical compounds with biological activity that can be useful in controlling diseases and symptoms that affect populations. These compounds are referred to as active pharmaceutical ingredients and may, in the solid state, present different crystal arrangements of its molecules (polymorphism). To each one of these crystalline arrays are associated physicochem...

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Diversity in Single- and Multiple-Component Crystals. The Search for and Prevalence of Polymorphs and Cocrystals

Cited by 489 publications

References 105 publications

Preparation and solid state characterisation of chlorothiazide sodium intermolecular self-assembly suprastructure

Preparation and solid state characterisation of chlorothiazide sodium intermolecular self-assembly suprastructure

Even–odd effect in the co-crystals of pyrazine and dicarboxylic acids

Caracterização de estado sólido de insumos farmacêuticos ativos: clorpropamida, nevirapina e dietilcarbamazina

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