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The use of green protic ionic liquids in the crystallization of isoniazid: Evaluation of physicochemical and biological properties of drug.
Reis, Carla Luzia Borges; Campelo, Thales Alves; Frota, Cristiane Cunha; Ayala, Alejandro Pedro; Silva, Lorena Mara Alexandre; Rocha, Maria Valderez Ponte; Santiago-Aguiar, Rílvia Saraiva de.
Afiliación
  • Reis CLB; Department of Chemical Engineering, Federal University of Ceará, Campus do Pici, Bloco 709, 60440-900 Fortaleza, Ceará, Brazil.
  • Campelo TA; Department of Pathology, Federal University of Ceará, Alexandre Baraúna St., 949, Rodolfo Teófilo, 60430-160 Fortaleza, Ceará, Brazil.
  • Frota CC; Department of Pathology, Federal University of Ceará, Alexandre Baraúna St., 949, Rodolfo Teófilo, 60430-160 Fortaleza, Ceará, Brazil.
  • Ayala AP; Department of Physics, Federal University of Ceará, Mister Hull Ave., Pici, 60440-900 Fortaleza, Ceará, Brazil.
  • Silva LMA; Embrapa Agroindústria Tropical, Dra. Sara Mesquita St., 2270, Pici, 60511-110 Fortaleza, Ceará, Brazil.
  • Rocha MVP; Department of Chemical Engineering, Federal University of Ceará, Campus do Pici, Bloco 709, 60440-900 Fortaleza, Ceará, Brazil.
  • Santiago-Aguiar RS; Department of Chemical Engineering, Federal University of Ceará, Campus do Pici, Bloco 709, 60440-900 Fortaleza, Ceará, Brazil. Electronic address: rilvia@ufc.br.
Eur J Pharm Biopharm ; 201: 114345, 2024 Aug.
Article en En | MEDLINE | ID: mdl-38823540
ABSTRACT
This study evaluated the synthesis of protic ionic liquids (PILs), 2-hydroxy ethylammonium formate (2-HEAF) and 2-hydroxy ethylammonium acetate (2-HEAA), and their applicability in the crystallization process of the active pharmaceutical ingredient isoniazid (INH) as anti-solvent. Isoniazid is an antibiotic used in the treatment of tuberculosis infections, being used as a first-line chemotherapeutic agent against Mycobacterium tuberculosis. Futhermore, this investigation was conducted in order to evaluate how these PILs can influence the habit, solubility, stability, and therapeutic efficiency of the obtained isoniazid crystals. The 2-HEAF and 2-HEAA PILs were easily formed in reactions between ethanolamine and carboxylic acids (formic or acetic acid), and they have no toxicity against Artemia salina. The PILs were able to crystallize isoniazid, influencing the crystal habit and size. The greatest variations in the hydrogen signals of the NH2 and NH groups of the amine and low variations in the chemical shifts of the hydrogens of the cation of the ethanolamine group from 2-HEAA and 2-HEAF indicate that PILs establish possibly weak interactions with INH. The obtained crystals were amorphous and showed higher solubility in water than standard INH. Moreover, these crystals showed therapeutic efficiency inantimycobacterial activity to inhibit the growth of Mycobacterium tuberculosis. The INH2-HEAF only degraded 5.1 % (w/w), however, INH2-HEAA degraded 32.8 % (w/w) after 60 days in an accelerated atmosphere. Then, the 2-HEAA and 2-HEAF were able to crystallize isoniazid, being a new application for these PILs. The used PILs also influenced the characteristics of isoniazid crystals.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Solubilidad / Cristalización / Líquidos Iónicos / Isoniazida / Antituberculosos Límite: Animals Idioma: En Revista: Eur J Pharm Biopharm Asunto de la revista: FARMACIA / FARMACOLOGIA Año: 2024 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Países Bajos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Solubilidad / Cristalización / Líquidos Iónicos / Isoniazida / Antituberculosos Límite: Animals Idioma: En Revista: Eur J Pharm Biopharm Asunto de la revista: FARMACIA / FARMACOLOGIA Año: 2024 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Países Bajos