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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Fluconazole: Synthesis and Structural Characterization of Four New Pharmaceutical Cocrystal Forms

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Author(s):
Owoyemi, Bolaji C. Dayo [1] ; da Silva, Cecilia C. P. [1] ; Souza, Matheus S. [2] ; Diniz, Luan F. [2] ; Ellena, Javier [2] ; Carneiro, Renato L. [1]
Total Authors: 6
Affiliation:
[1] Fed Univ Sao Carlos UFSCar, Dept Chem, Rod Washington Luis Km 235, BR-13560905 Sao Carlos, SP - Brazil
[2] Univ Sao Paulo, Inst Fis Sao Carlos, CP 369, BR-13560970 Sao Carlos, SP - Brazil
Total Affiliations: 2
Document type: Journal article
Source: Crystal Growth & Design; v. 19, n. 2, p. 648-657, FEB 2019.
Web of Science Citations: 3
Abstract

Pharmaceutical cocrystals have emerged over the past several decades as an alternative path for synthesizing stable and/or improved crystalline forms of active pharmaceutical ingredients. In this contribution, we developed a reproducible cocrystallization path for the supramolecular synthesis of four new pharmaceutical cocrystal forms of fluconazole (FLZ), an antifungal multifunctional drug: fluconazole- fumaric acid monohydrate (1:1:1), fluconazole-malic acid (1:1), fluconazole- dipicolinic acid (1:1), and fluconazole-adipic acid (1:1). All the new cocrystals were characterized by powder/single-crystal X-ray diffraction, Raman, Fourier transform infrared spectroscopy, differential scanning calorimetry/thermogravimetric analysis, and hot-stage polarized optical microscopy, and their water solubility was determined. Structurally, although the coformers were different, the same strong O-H center dot center dot center dot N hydrogen bond between the FLZ molecule and the coformers was observed. The aqueous solubility studies revealed that all the cocrystals were found to exhibit improved aqueous solubility when compared to the commercialized FLZ polymorph. (AU)

FAPESP's process: 15/25694-0 - Obtaining, characterization and evaluation of novel crystalline solid forms of drugs used treatment of tuberculosis
Grantee:Luan Farinelli Diniz
Support Opportunities: Scholarships in Brazil - Master
FAPESP's process: 10/16520-5 - Application of calibration chemometrics methods and multivariate curve resolution in Raman spectroscopy for qualitative, quantitative and polymorphism analyses in medicines
Grantee:Renato Lajarim Carneiro
Support Opportunities: Regular Research Grants