Enhancement of solubility of albendazole by complexation with β-cyclodextrin

Moriwaki, Cristiane; Costa, Glauciane L.; Ferracini, C; Moraes, Flávio Faria de; Zanin, Gisella Maria; Pineda, Edgardo Alfonso Gómez; Matioli, Graciette

doi:10.1590/s0104-66322008000200005

Cited by 47 publications

(34 citation statements)

References 12 publications

(35 reference statements)

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“…ABZ is the API most widely used for controlling intestinal parasites, because it has broad-spectrum activity, is well tolerated, and has low cost (Moriwaki et al, 2008). According to the National Health Surveillance Agency (AN-VISA), the reference drug is Zentel ® (GlaxoSmithKline), and currently, there are 11 types of generic medications from several pharmaceutical laboratories in Brazil.…”

Section: Introductionmentioning

confidence: 99%

Assay and physicochemical characterization of the antiparasitic albendazole

Cavalcanti

Sousa²,

Tabosa

et al. 2012

Braz. J. Pharm. Sci.

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The aim of this study was to characterize three batches of albendazole by pharmacopeial and complementary analytical techniques in order to establish more detailed specifications for the development of pharmaceutical forms. The ABZ01, ABZ02, and ABZ03 batches had melting points of 208 °C, 208 °C, and 209 °C, respectively. X-ray diffraction revealed that all three batches showed crystalline behavior and the absence of polymorphism. Scanning electron microscopy showed that all the samples were crystals of different sizes with a strong tendency to aggregate. The samples were insoluble in water (5.07, 4.27, and 4.52 mg mL -1 , respectively) and very slightly soluble in 0.1 M HCl (55.10, 56.90, and 61.70 mg mL -1 , respectively) and additionally showed purities within the range specified by the Brazilian Pharmacopoeia 5th edition (F. Bras. V; 98% to 102%). The pharmacopeial assay method was not reproducible and some changes were necessary. The method was validated and showed to be selective, specific, linear, robust, precise, and accurate. From this characterization, we concluded that pharmacopeial techniques alone are not able to detect subtle differences in active pharmaceutical ingredients; therefore, the use of other complementary techniques is required to ensure strict quality control in the pharmaceutical industry.Uniterms: Albendazole/characterization. Antiparasitics/quality control.O objetivo do trabalho foi caracterizar três lotes de albendazol com técnicas analíticas farmacopéicas e complementares a fim de estabelecer especificações mais detalhadas para o desenvolvimento de formas farmacêuticas. Os lotes ABZ01, ABZ02 e ABZ03 apresentaram fusão em 208 °C, 208 °C e 209 °C. Foi possível evidenciar, por difração de raios X, que os três lotes apresentaram comportamento cristalino e ausência de polimorfismo. Através da microscopia eletrônica de varredura verificou-se que todas as amostras apresentaram cristais com diferentes tamanhos e forte tendência de agregação. As amostras foram insolúveis em água (5,07; 4,27 e 4,52 µg mL -1 ) e muito pouco solúveis em HCl 0,1M (55,10; 56,90 e 61,70 µg mL -1 ) e, ainda, apresentaram pureza dentro da faixa especificada pela F.Bras.V (98% a 102%). O método farmacopéico de doseamento não foi reprodutível, e algumas mudanças foram necessárias. O método foi validado e demonstrou ser seletivo, específico, linear, robusto, preciso e exato. A partir dessa caracterização, pode-se concluir que apenas técnicas farmacopéicas não são capazes de detectar diferenças sutis entre os ingredientes farmacêuticos ativos, necessitando, portanto, de uso de outras técnicas complementares para garantir um rígido controle de qualidade na indústria farmacêutica.Unitermos: Albendazol/caracterização. Antiparasitários/controle de qualidade.

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Section: Introductionmentioning

confidence: 99%

Assay and physicochemical characterization of the antiparasitic albendazole

Cavalcanti

Sousa²,

Tabosa

et al. 2012

Braz. J. Pharm. Sci.

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“…The CD molecules are externally hydrophilic and relatively hydrophobic inside their ring cavity. In liquid or occasionally solid media, CDs are able to form inclusion complexes with many different types of appropriately sized, preferentially nonpolar molecules [5][6][7]. They have received considerable attention in pharmaceutical application because they improve water solubility, chemical stability, and bioavailability of various drugs through the formation of inclusion complexes [8].…”

Section: Introductionmentioning

confidence: 99%

“…Derivatization, such as that in HP-b-CD, increases aqueous solubility by imparting greater flexibility to the external hydroxyl groups, which also have the potential to increase hydrogen bond formation between the guest molecule and the derivatized CD and, consequently, may increase the stability of the inclusion complex. With a relatively low price, HP-b-CD has a broad prospect in practical application [6,7,9,10].…”

Section: Introductionmentioning

confidence: 99%

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Enrofloxacin inclusion complexes with cyclodextrins

Calsavara

Zanin

Moraes

2011

J Incl Phenom Macrocycl Chem

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Inclusion complexes using a-, b-, c-, and hydroxypropyl-b-CD (HP-b-CD) were produced with the antibiotic enrofloxacin, with the aim of increasing its solubility by complexation. Phase solubility diagrams were obtained, to confirm the formation of inclusion complexes, and to determine the solubility enhancement and stability constant of each complex. Enrofloxacin inclusion in b-CD showed the highest value of the complex stability constant (35.56 mmol L -1 ), but the greatest increase in solubility was obtained using HP-b-CD reaching a 1258% increase over enrofloxacin solubility in the absence of CD. The order of highest enrofloxacin solubility achieved was: HPb-CD [ a-CD [ c-CD [ b-CD. In addition, formation of complexes was confirmed by differential scanning calorimetry and thermogravimetry, applied to the complexes obtained by the kneading technique. The influence of citric acid, alone or as an adjunct of b-CD, on the solubility of enrofloxacin was also determined. A solution of 15 mmol L -1 citric acid dissolved 10 g L -1 of enrofloxacin, but a gradual increase in b-CD concentration in the presence of citric acid did not increase the degree of solubilization of enrofloxacin.

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“…The unusual shape of CD makes them able to include a range of organic and inorganic molecules via non-covalent interactions. [12][13][14] Unsubstituted β-CD has poor water solubility (16 mg ml −1 at 25°C), whereas random substitution of the hydroxyl groups by alkyl or hydroxyalkyl groups is able to increase the solubility. Therefore, several synthetically modified β-CDs, such as methyl-β-cyclodextrin (Me-β-CD), were used as multifunctional drug carriers.…”

Section: Introductionmentioning

confidence: 99%

A Phase Solubility Study on the Chiral Discrimination of Ibuprofen by β-Cyclodextrin Complexes

et al. 2011

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The effects of chiral discrimination in inclusion complexes formed by native β-cyclodextrin and its substituted form (namely methyl-β-cyclodextrin) with racemate or pure enantiomers of the non-steroidal antiinflammatory drug ibuprofen have been investigated in water. Stability constants and complexation efficiency have been determined for these host-guest systems with a 1:1 molar ratio from phase solubility profiles, showing that in aqueous solution, methylated cyclodextrin is a better complex agent than native cyclodextrin, with more enhanced effects for the (R)-enantiomer. These results have been validated using NMR technique. In particular, 1 H NMR spectra in D 2 O show a splitting of the signals for the methyl group and the aromatic protons close to the asymmetric centre of the racemate ibuprofen included in cyclodextrin cavity.

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Enhancement of solubility of albendazole by complexation with β-cyclodextrin

Cited by 47 publications

References 12 publications

Assay and physicochemical characterization of the antiparasitic albendazole

Assay and physicochemical characterization of the antiparasitic albendazole

Enrofloxacin inclusion complexes with cyclodextrins

A Phase Solubility Study on the Chiral Discrimination of Ibuprofen by β-Cyclodextrin Complexes

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