Effect of different variables in the solubility of ampicillin and corresponding solid phase

Detalhes bibliográficos
Autor(a) principal: Chiavone Filho, Osvaldo
Data de Publicação: 2018
Outros Autores: Bezerra, Ítalla Medeiros, Moreira, Leila Cabral, Mattedi, Silvana
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UFRN
Texto Completo: https://repositorio.ufrn.br/handle/123456789/44976
Resumo: Ampicillin belongs to the class of beta-lactam antibiotics, which corresponds the most prescribed antibiotics in medicine. This justifies the importance of elucidating the effect of several variables for the synthesis process (pH, temperature, co-solvent) on the behavior of the compounds involved in the enzymatic reaction. This paper aims to present new ampicillin solubility data in aqueous medium and the characterization of the solid phase of the antibiotic. In the phase equilibrium experiments it was considered the effect of pH (3 up to 7.5), temperature (283.15 K up to 298.15 K) and the ethanol concentration in the aqueous solution (varying between 0 and 70 wt% ethanol). The solubility curves deviate from U-shape solubility curves with respect to pH in the range of 0e70 wt%. This is due to ampicillin anhydrous becomes trihydrated molecule in the solid phase at alkaline pH region, changing the antibiotic properties significantly. This change in crystalline structure was confirmed by characterization of antibiotic solid phase carried out from thermogravimetric (TGA), Fourier Transform Infrared (FTIR) spectroscopy, Scanning Electron Microscopy (SEM) and X-ray Diffraction (XRD) analyses. Dissociation constants have also been measured at the studied values of temperature and ethanol composition, using potentiometric titration. Finally, a thermodynamic model considering the ideal solution was applied to describe mathematically the solubility curves measured close to experimental uncertainties
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spelling Chiavone Filho, OsvaldoBezerra, Ítalla MedeirosMoreira, Leila CabralMattedi, Silvana2021-11-22T20:45:49Z2021-11-22T20:45:49Z2018-03-15BEZERRA, I.M.; MOREIRA, L.C.; CHIAVONE-FILHO, O.; MATTEDI, S.. Effect of different variables in the solubility of ampicillin and corresponding solid phase. FLUID PHASE EQUILIBRIA, v. 459, p. 18-29, 2017. Disponível em: https://www.sciencedirect.com/science/article/abs/pii/S0378381217304715?via%3Dihub. Acesso em: 29 jun. 2021. https://doi.org/10.1016/j.fluid.2017.11.033.0378-3812https://repositorio.ufrn.br/handle/123456789/4497610.1016/j.fluid.2017.11.033ElsevierAttribution 3.0 Brazilhttp://creativecommons.org/licenses/by/3.0/br/info:eu-repo/semantics/openAccessb-Lactam antibioticEthanolSolid-liquid equilibriumDissociation constantSolid compositionEffect of different variables in the solubility of ampicillin and corresponding solid phaseinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleAmpicillin belongs to the class of beta-lactam antibiotics, which corresponds the most prescribed antibiotics in medicine. This justifies the importance of elucidating the effect of several variables for the synthesis process (pH, temperature, co-solvent) on the behavior of the compounds involved in the enzymatic reaction. This paper aims to present new ampicillin solubility data in aqueous medium and the characterization of the solid phase of the antibiotic. In the phase equilibrium experiments it was considered the effect of pH (3 up to 7.5), temperature (283.15 K up to 298.15 K) and the ethanol concentration in the aqueous solution (varying between 0 and 70 wt% ethanol). The solubility curves deviate from U-shape solubility curves with respect to pH in the range of 0e70 wt%. This is due to ampicillin anhydrous becomes trihydrated molecule in the solid phase at alkaline pH region, changing the antibiotic properties significantly. This change in crystalline structure was confirmed by characterization of antibiotic solid phase carried out from thermogravimetric (TGA), Fourier Transform Infrared (FTIR) spectroscopy, Scanning Electron Microscopy (SEM) and X-ray Diffraction (XRD) analyses. Dissociation constants have also been measured at the studied values of temperature and ethanol composition, using potentiometric titration. Finally, a thermodynamic model considering the ideal solution was applied to describe mathematically the solubility curves measured close to experimental uncertaintiesengreponame:Repositório Institucional da UFRNinstname:Universidade Federal do Rio Grande do Norte (UFRN)instacron:UFRNCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8914https://repositorio.ufrn.br/bitstream/123456789/44976/2/license_rdf4d2950bda3d176f570a9f8b328dfbbefMD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81484https://repositorio.ufrn.br/bitstream/123456789/44976/3/license.txte9597aa2854d128fd968be5edc8a28d9MD53123456789/449762023-02-06 15:47:38.548oai:https://repositorio.ufrn.br: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Repositório de PublicaçõesPUBhttp://repositorio.ufrn.br/oai/opendoar:2023-02-06T18:47:38Repositório Institucional da UFRN - Universidade Federal do Rio Grande do Norte (UFRN)false
dc.title.pt_BR.fl_str_mv Effect of different variables in the solubility of ampicillin and corresponding solid phase
title Effect of different variables in the solubility of ampicillin and corresponding solid phase
spellingShingle Effect of different variables in the solubility of ampicillin and corresponding solid phase
Chiavone Filho, Osvaldo
b-Lactam antibiotic
Ethanol
Solid-liquid equilibrium
Dissociation constant
Solid composition
title_short Effect of different variables in the solubility of ampicillin and corresponding solid phase
title_full Effect of different variables in the solubility of ampicillin and corresponding solid phase
title_fullStr Effect of different variables in the solubility of ampicillin and corresponding solid phase
title_full_unstemmed Effect of different variables in the solubility of ampicillin and corresponding solid phase
title_sort Effect of different variables in the solubility of ampicillin and corresponding solid phase
author Chiavone Filho, Osvaldo
author_facet Chiavone Filho, Osvaldo
Bezerra, Ítalla Medeiros
Moreira, Leila Cabral
Mattedi, Silvana
author_role author
author2 Bezerra, Ítalla Medeiros
Moreira, Leila Cabral
Mattedi, Silvana
author2_role author
author
author
dc.contributor.author.fl_str_mv Chiavone Filho, Osvaldo
Bezerra, Ítalla Medeiros
Moreira, Leila Cabral
Mattedi, Silvana
dc.subject.por.fl_str_mv b-Lactam antibiotic
Ethanol
Solid-liquid equilibrium
Dissociation constant
Solid composition
topic b-Lactam antibiotic
Ethanol
Solid-liquid equilibrium
Dissociation constant
Solid composition
description Ampicillin belongs to the class of beta-lactam antibiotics, which corresponds the most prescribed antibiotics in medicine. This justifies the importance of elucidating the effect of several variables for the synthesis process (pH, temperature, co-solvent) on the behavior of the compounds involved in the enzymatic reaction. This paper aims to present new ampicillin solubility data in aqueous medium and the characterization of the solid phase of the antibiotic. In the phase equilibrium experiments it was considered the effect of pH (3 up to 7.5), temperature (283.15 K up to 298.15 K) and the ethanol concentration in the aqueous solution (varying between 0 and 70 wt% ethanol). The solubility curves deviate from U-shape solubility curves with respect to pH in the range of 0e70 wt%. This is due to ampicillin anhydrous becomes trihydrated molecule in the solid phase at alkaline pH region, changing the antibiotic properties significantly. This change in crystalline structure was confirmed by characterization of antibiotic solid phase carried out from thermogravimetric (TGA), Fourier Transform Infrared (FTIR) spectroscopy, Scanning Electron Microscopy (SEM) and X-ray Diffraction (XRD) analyses. Dissociation constants have also been measured at the studied values of temperature and ethanol composition, using potentiometric titration. Finally, a thermodynamic model considering the ideal solution was applied to describe mathematically the solubility curves measured close to experimental uncertainties
publishDate 2018
dc.date.issued.fl_str_mv 2018-03-15
dc.date.accessioned.fl_str_mv 2021-11-22T20:45:49Z
dc.date.available.fl_str_mv 2021-11-22T20:45:49Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.citation.fl_str_mv BEZERRA, I.M.; MOREIRA, L.C.; CHIAVONE-FILHO, O.; MATTEDI, S.. Effect of different variables in the solubility of ampicillin and corresponding solid phase. FLUID PHASE EQUILIBRIA, v. 459, p. 18-29, 2017. Disponível em: https://www.sciencedirect.com/science/article/abs/pii/S0378381217304715?via%3Dihub. Acesso em: 29 jun. 2021. https://doi.org/10.1016/j.fluid.2017.11.033.
dc.identifier.uri.fl_str_mv https://repositorio.ufrn.br/handle/123456789/44976
dc.identifier.issn.none.fl_str_mv 0378-3812
dc.identifier.doi.none.fl_str_mv 10.1016/j.fluid.2017.11.033
identifier_str_mv BEZERRA, I.M.; MOREIRA, L.C.; CHIAVONE-FILHO, O.; MATTEDI, S.. Effect of different variables in the solubility of ampicillin and corresponding solid phase. FLUID PHASE EQUILIBRIA, v. 459, p. 18-29, 2017. Disponível em: https://www.sciencedirect.com/science/article/abs/pii/S0378381217304715?via%3Dihub. Acesso em: 29 jun. 2021. https://doi.org/10.1016/j.fluid.2017.11.033.
0378-3812
10.1016/j.fluid.2017.11.033
url https://repositorio.ufrn.br/handle/123456789/44976
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv Attribution 3.0 Brazil
http://creativecommons.org/licenses/by/3.0/br/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution 3.0 Brazil
http://creativecommons.org/licenses/by/3.0/br/
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFRN
instname:Universidade Federal do Rio Grande do Norte (UFRN)
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