Solubility and solution thermodynamics of acetaminophen in (ethanol + propylene glycol + water) ternary mixtures

ilustraciones, gráficas, tablas

Autores:
Romdhani, Asma
Tipo de recurso:
Fecha de publicación:
2022
Institución:
Universidad Nacional de Colombia
Repositorio:
Universidad Nacional de Colombia
Idioma:
eng
OAI Identifier:
oai:repositorio.unal.edu.co:unal/82880
Acceso en línea:
https://repositorio.unal.edu.co/handle/unal/82880
https://repositorio.unal.edu.co/
Palabra clave:
610 - Medicina y salud::615 - Farmacología y terapéutica
Termoquímica
Ensayo de acetaminofén
Thermochemistry
Acetaminophen Assay
Acetaminophen
(Ethanol + propylene glycol + water) mixtures
Solubility
Jouyban-Acree model
Dissolution thermodynamics
Apparent specific volume
Acetaminofeno
Mezclas (etanol + propilenglicol + agua)
Solubilidad
Modelo de Jouyban-Acree
Termodinámica de disolución
Volumen específico aparente
Rights
openAccess
License
Reconocimiento 4.0 Internacional
id UNACIONAL2_e441876ed72176f646469b67b3620a8f
oai_identifier_str oai:repositorio.unal.edu.co:unal/82880
network_acronym_str UNACIONAL2
network_name_str Universidad Nacional de Colombia
repository_id_str
dc.title.eng.fl_str_mv Solubility and solution thermodynamics of acetaminophen in (ethanol + propylene glycol + water) ternary mixtures
dc.title.translated.spa.fl_str_mv Solubilidad y termodinámica de disolución de acetaminofeno en mezclas ternarias (etanol + propilenglicol + agua)
title Solubility and solution thermodynamics of acetaminophen in (ethanol + propylene glycol + water) ternary mixtures
spellingShingle Solubility and solution thermodynamics of acetaminophen in (ethanol + propylene glycol + water) ternary mixtures
610 - Medicina y salud::615 - Farmacología y terapéutica
Termoquímica
Ensayo de acetaminofén
Thermochemistry
Acetaminophen Assay
Acetaminophen
(Ethanol + propylene glycol + water) mixtures
Solubility
Jouyban-Acree model
Dissolution thermodynamics
Apparent specific volume
Acetaminofeno
Mezclas (etanol + propilenglicol + agua)
Solubilidad
Modelo de Jouyban-Acree
Termodinámica de disolución
Volumen específico aparente
title_short Solubility and solution thermodynamics of acetaminophen in (ethanol + propylene glycol + water) ternary mixtures
title_full Solubility and solution thermodynamics of acetaminophen in (ethanol + propylene glycol + water) ternary mixtures
title_fullStr Solubility and solution thermodynamics of acetaminophen in (ethanol + propylene glycol + water) ternary mixtures
title_full_unstemmed Solubility and solution thermodynamics of acetaminophen in (ethanol + propylene glycol + water) ternary mixtures
title_sort Solubility and solution thermodynamics of acetaminophen in (ethanol + propylene glycol + water) ternary mixtures
dc.creator.fl_str_mv Romdhani, Asma
dc.contributor.advisor.none.fl_str_mv Martínez Rodríguez, Fleming
dc.contributor.author.none.fl_str_mv Romdhani, Asma
dc.contributor.researchgroup.spa.fl_str_mv Grupo de Investigaciones Farmacéutico-Fisicoquímicas
dc.contributor.cvlac.spa.fl_str_mv Romdhani, Asma [https://scienti.minciencias.gov.co/cvlac/visualizador/generarCurriculoCv.do?cod_rh=0000117660]
dc.contributor.scopus.spa.fl_str_mv Romdhani, Asma [https://www-scopus-com.ezproxy.unal.edu.co/authid/detail.uri?origin=resultslist&authorId=54901767600&zone=]
dc.contributor.researchgate.spa.fl_str_mv Romdhani, Asma [https://www.researchgate.net/profile/Asma-Romdhani]
dc.contributor.googlescholar.spa.fl_str_mv Romdhani, Asma [https://scholar.google.com/citations?user=gKs1hk0AAAAJ]
dc.subject.ddc.spa.fl_str_mv 610 - Medicina y salud::615 - Farmacología y terapéutica
topic 610 - Medicina y salud::615 - Farmacología y terapéutica
Termoquímica
Ensayo de acetaminofén
Thermochemistry
Acetaminophen Assay
Acetaminophen
(Ethanol + propylene glycol + water) mixtures
Solubility
Jouyban-Acree model
Dissolution thermodynamics
Apparent specific volume
Acetaminofeno
Mezclas (etanol + propilenglicol + agua)
Solubilidad
Modelo de Jouyban-Acree
Termodinámica de disolución
Volumen específico aparente
dc.subject.other.spa.fl_str_mv Termoquímica
Ensayo de acetaminofén
dc.subject.other.eng.fl_str_mv Thermochemistry
Acetaminophen Assay
dc.subject.proposal.eng.fl_str_mv Acetaminophen
(Ethanol + propylene glycol + water) mixtures
Solubility
Jouyban-Acree model
Dissolution thermodynamics
Apparent specific volume
dc.subject.proposal.spa.fl_str_mv Acetaminofeno
Mezclas (etanol + propilenglicol + agua)
Solubilidad
Modelo de Jouyban-Acree
Termodinámica de disolución
Volumen específico aparente
description ilustraciones, gráficas, tablas
publishDate 2022
dc.date.issued.none.fl_str_mv 2022-08
dc.date.accessioned.none.fl_str_mv 2023-01-11T19:53:01Z
dc.date.available.none.fl_str_mv 2023-01-11T19:53:01Z
dc.type.spa.fl_str_mv Trabajo de grado - Maestría
dc.type.driver.spa.fl_str_mv info:eu-repo/semantics/masterThesis
dc.type.version.spa.fl_str_mv info:eu-repo/semantics/acceptedVersion
dc.type.content.spa.fl_str_mv Text
dc.type.redcol.spa.fl_str_mv http://purl.org/redcol/resource_type/TM
status_str acceptedVersion
dc.identifier.uri.none.fl_str_mv https://repositorio.unal.edu.co/handle/unal/82880
dc.identifier.instname.spa.fl_str_mv Universidad Nacional de Colombia
dc.identifier.reponame.spa.fl_str_mv Repositorio Institucional Universidad Nacional de Colombia
dc.identifier.repourl.spa.fl_str_mv https://repositorio.unal.edu.co/
url https://repositorio.unal.edu.co/handle/unal/82880
https://repositorio.unal.edu.co/
identifier_str_mv Universidad Nacional de Colombia
Repositorio Institucional Universidad Nacional de Colombia
dc.language.iso.spa.fl_str_mv eng
language eng
dc.relation.references.spa.fl_str_mv Agostinho, D.A.S.; Jesus, A.R.; Silva, A.B.P.; Esperança, J.M.S.S.; Paiva, A.; Duarte, A.R.C.; Reis, P.M. (2021), Improvement of new dianionic ionic liquids vs monoanionic in solubility of poorly water-soluble drugs, Journal of Pharmaceutical Sciences, 110, 2489–2500.
Ahumada, E.A. (2012), Estudio fisicoquímico de la solubilidad de acetaminofeno en mezclas polietilenglicol 400 + agua, Tesis de Maestría en Ciencias Farmacéuticas Universidad Nacional de Colombia, Bogotá D.C.
Ahumada, E.A.; Delgado, D.R.; Martínez, F. (2012a), Solution thermodynamics of acetaminophen in some PEG 400 + water mixtures, Fluid Phase Equilibria, 332, 120–127.
Ahumada, E.A.; Delgado, D.R.; Martínez, F. (2012b), Corrigendum to “Solution thermodynamics of acetaminophen in some PEG 400 + water mixtures” [Fluid Phase Equilibr. 332 (2012) 120–127], Fluid Phase Equilibria, 334, 204.
Aulton, M.E. (2002), Pharmaceutics: The Science of Dosage Forms Design, 2nd ed., Churchill Livingstone, London.
Avdeef, A. (2003), Absorption and Drug Development, Solubility, Permeability and Charge State, Wiley-Interscience, Hoboken (NJ).
Baena, Y.; Pinzón, J.A.; Barbosa, H.; Martínez, F. (2004), Temperature dependence of the solubility of some acetanilide derivatives in several organic and aqueous solvents, Physics and Chemistry of Liquids, 42, 603–613.
Barrante, J.R. (2003), Applied Mathematics for Physical Chemistry, 3rd ed., Prentice Hall, Upper Saddle River (NJ).
Barton, A.F.M. (1991), Handbook of Solubility Parameters and Other Cohesion Parameters, 2nd ed., CRC Press, Boca Raton (FL).
Bashpa, P.; Bijudas, K.; Tom, A.M.; Archana, P.K.; Murshida, K.P.; Noufala-Banu, K.; Amritha, K.R.; Vimisha, K. (2014), Polymorphism of paracetamol: A comparative study on commercial paracetamol samples, International Journal of Chemical Studies, 1, 25–29.
Bevington, P.R.; Robinson, D.K. (2003), Data Reduction and Error Analysis for the Physical Sciences, 3rd ed., McGraw-Hill Education, Co., New York (NY), pp. 36–49.
Blanco, L.H. (2010), Plan de Gestión Integral de Residuos o Desechos Peligrosos de la Universidad Nacional de Colombia –Sede Bogotá (RESPEL), Facultad de Ingeniería, Universidad Nacional de Colombia, Bogotá.
Bolaños, C.I.; Erazo, E.A.; Luengas, P.; Barbosa, H.; Martínez, F. (1999), Solubilidad de acetaminofén en los sistemas agua-alcohol USP-jarabe USP y agua-alcohol USP-sorbitol USP, Revista Colombiana de Ciencias Químico Farmacéuticas, 28, 71–75.
Budavari, S.; O’Neil, M.J.; Smith, A.; Heckelman, P.E., Obenchain, J.R., Jr.; Gallipeau, J.A.R.; D’Arecea, M.A. (editors) (2001), The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 13th ed., Merck & Co., Inc., Whitehouse Station (NJ).
Bustamante, P.; Romero, S.; Reillo, A. (1995), Thermodynamics of paracetamol in amphiprotic and amphiprotic-aprotic solvent mixtures, Pharmacy and Pharmacology Communications, 1, 505–507.
Bustamante, P.; Romero, S.; Peña, A.; Escalera, B.; Reillo, A. (1998), Nonlinear enthalpy-entropy compensation for the solubility of drugs in solvent mixtures: paracetamol, acetanilide and nalidixic acid in dioxane-water, Journal of Pharmaceutical Sciences, 87, 1590–1596.
Cárdenas, C.A., Guevara, C.C. (2003), Solubilidad y volúmenes de desplazamiento del acetaminofén en mezclas agua-propilenoglicol y etanol-propilenoglicol a 25 °C, Trabajo de Grado, Carrera de Farmacia, Universidad Nacional de Colombia, Bogotá D.C.
Cárdenas, Z.J.; Jiménez, D.M.; Martínez, F. (2015), Solubility and saturation apparent volume of propranolol.HCl in some binary aqueous cosolvent mixtures at 298.15 K, Journal of Chemical and Engineering Data, 60, 1520–1525.
Carstensen, J.T. (1996), Modeling and data treatment in the pharmaceutical sciences, Technomic Publishing Co., Inc., Lancaster (PA), 127–159.
Chirumbolo, S. (2021), Paracetamol in the home treatment of early COVID‐19 symptoms: A possible foe rather than a friend for elderly patients? Journal of Medical Virology, 93, 5704–5706.
Connors, K.A. (2002), Thermodynamics of Pharmaceutical Systems: An Introduction for Students of Pharmacy, Wiley–Interscience, Hoboken (NJ).
Connors, K.A.; Amidon, G.L.; Stella, V.J. (1986), Chemical Stability of Pharmaceuticals: A Handbook for Pharmacists, 2nd ed., John Wiley & Sons, New York (NY).
Coronado, Y.P.; Fonseca, J.C.; Luengas, P.E.; Barbosa, H.J.; Martínez, F. (1999), Solubilidad de acetaminofén en sistemas solventes agua-alcohol-poliol, Revista Colombiana de Ciencias Químico Farmacéuticas, 28, 59–63.
Crighton, A.J.; McCann, C.T.; Todd, E.J.; Brown, A.J. (2020), Safe use of paracetamol and high-dose NSAID analgesia in dentistry during the COVID-19 pandemic, British Dental Journal, 229(1), 15–18.
Delgado, D.R.; Martinez, F. (2013a), Solution thermodynamics of sulfadiazine in ethanol + water mixtures, Journal of Molecular Liquids, 187, 99–105.
Delgado, D.R.; Martínez, F. (2013b), Solubility and solution thermodynamics of sulfamerazine and sulfamethazine in some ethanol + water mixtures, Fluid Phase Equilibria, 360, 88–96.
Delgado, D.R.; Rodríguez, G.A.; Martínez, F. (2013), Thermodynamic study of the solubility of sulfapyridine in some ethanol + water mixtures, Journal of Molecular Liquids, 177, 156–161.
Delgado, D.R.; Almanza, O.A.; Martínez, F.; Peña, M.A.; Jouyban, A.; Acree, W.E., Jr. (2016), Solution thermodynamics and preferential solvation of sulfamethazine in (methanol + water) mixtures, Journal of Chemical Thermodynamics, 97, 264–276.
Echeverry, L.C.; Muñoz, M.M.; Tinjacá, D.A.; Martinez, F.; Peña, M.A.; Rahimpour, E.; Jouyban, A.; Acree, W.E., Jr. (2019), Equilibrium solubility and apparent specific volume of lidocaine.HCl.H2O in some {cosolvent (1) + water (2)} mixtures at 298.2 K, Physics and Chemistry of Liquids, 57, 679–688.
Espeau, P.; Céolin, R.; Tamarit, J.L.; Perrin, M.A.; Gauchi, J.P.; Leveiller, F. (2005), Polymorphism of paracetamol: Relative stabilities of the monoclinic and orthorhombic phases inferred from topological pressure-temperature and temperature-volume phase diagrams, Journal of Pharmaceutical Sciences, 94, 524–539.
Etman, M.A.; Naggar, V.F. (1990), Thermodynamics of paracetamol solubility in sugar-water cosolvent systems, International Journal of Pharmaceutics, 58, 177–184.
Faroongsarng, D., Kadejinda, W., Sunthornpit, A. (2000), Thermal behavior of a pharmaceutical solid acetaminophen doped with p-aminophenol, AAPS PharmSciTech, 1(3), article 23.
Fedors, R.F. (1974), A method for estimating both the solubility parameters and molar volumes of liquids, Polymer Engineering and Science, 14, 147–154.
Ferro, V.; Ávila, P. (1986), Perfiles de solubilidad en diferentes sistemas solventes para algunos derivados de la anilina con acción antipirética-analgésica, Tesis de Grado, Departamento de Farmacia, Universidad Nacional de Colombia, Bogotá D.E.
Florence, A.T.; Attwood, D. (2006), Physicochemical Principles of Pharmacy, 4th ed., Pharmaceutical Press, London.
Fonseca, J.C.; Coronado, Y.P. (1998), Determinación de la solubilidad de acetaminofén en sistemas ternarios. Parte II. Sistemas agua-alcohol-poliol, Tesis de Grado, Carrera de Farmacia, Universidad Nacional de Colombia, Santafé de Bogotá, D.C.
Grant, D.J.W.; Mehdizadeh, M., Chow, A.H.L.; Fairbrother, J.E. (1984), Nonlinear van’t Hoff solubility-temperature plots and their pharmaceutical interpretation, International Journal of Pharmaceutics, 18, 25–38.
Hamza, Y.E.; Paruta, A.N. (1985), Solubilization of paracetamol using nonionic surfactants and cosolubilizers, Drug Development and Industrial Pharmacy, 11, 187-206.
Hatefi, A.; Jouyban, A.; Mohammadian, E., Acree, W.E., Jr.; Rahimpour, E. (2019), Prediction of paracetamol solubility in cosolvency systems at different temperatures, Journal of Molecular Liquids, 273, 282–291.
Jendrzejewska, I., Goryczka, T., Pietrasik, E., Klimontko, J., Jampilek, J. (2020), X-ray and thermal analysis of selected drugs containing acetaminophen, Molecules, 25, 5909.
Jesus, A.R.; Soromenho, M.R.C.; Raposo, L.R.; Esperança, J.M.S.S.; Baptista, P.V.; Fernandes, A.R.; Reis, P.M. (2019), Enhancement of water solubility of poorly water-soluble drugs by new biocompatible N-acetyl amino acid N-alkyl cholinium-based ionic liquids, European Journal of Pharmaceutics and Biopharmaceutics, 137, 227–232.
Jesus, A.R.; Raposo, L.R.; Soromenho, M.R.C.; Agostinho, D.A.S.; Esperança, J.M.S.S.; Baptista, P.V.; Fernandes, A.R.; Reis, P.M. (2021), New non-toxic N-alkyl cholinium-based ionic liquids as excipients to improve the solubility of poorly water-soluble drugs, Symmetry, 13, 2053.
Jiménez, J.A. (2005), Solubilidad de acetaminofén en mezclas binarias cosolventes formadas por agua, etanol y propilenoglicol en función de la temperatura, Trabajo de Grado, Departamento de Farmacia, Universidad Nacional de Colombia, Bogotá D.C.
Jiménez, F.; Martínez, F. (1995), Una estrategia para la selección sistemática de vehículos en el diseño de formas farmacéuticas liquidas homogéneas, Revista Colombiana de Ciencias Químico Farmacéuticas, 24, 19–23.
Jiménez, J.; Martínez, F. (2005a), Study of some volumetric properties of 1,2-propanediol + water mixtures at several temperatures, Revista Colombiana de Ciencias Químico Farmacéuticas, 34, 46–57.
Jiménez, J.A.; Martínez, F. (2005b), Thermodynamic magnitudes of mixing and solvation of acetaminophen in ethanol + water cosolvent mixtures, Revista de la Academia Colombiana de Ciencias, 30, 87–99.
Jiménez, J.; Martínez, F. (2006a), Volumetric properties of ethanol + 1,2-propanediol mixtures at different temperatures, Physics and Chemistry of Liquids, 44, 521–530.
Jiménez, J.A.; Martínez, F. (2006b), Temperature dependence of solubility of acetaminophen in propylene glycol + ethanol mixtures, Journal of Solution Chemistry, 35, 335–352.
Jiménez, J.A.; Martínez, F. (2006c), Thermodynamic study of the solubility of acetaminophen in propylene glycol + water cosolvent mixtures, Journal of the Brazilian Chemical Society, 17, 125–134.
Jiménez, J.; Manrique, J.; Martínez, F. (2004), Effect of temperature on some volumetric properties for ethanol + water mixtures, Revista Colombiana de Ciencias Químico Farmacéuticas, 33, 145–155.
Jiménez, J.A.; Guevara, C.C.; Cárdenas, C.A.; Pérez, D.C.; Barbosa, H.J.; Pinzón, J.A.; Martínez, F. (2005), Solubilidad y volúmenes de desplazamiento de algunos analgésicos en mezclas cosolventes a 25.0 °C, Proyecto de Investigación No 1.540 de 2003, Fundación para la Promoción de la Investigación y la Tecnología, Banco de la República, Bogotá D.C.
Jiménez, D.M.; Cárdenas, Z.J.; Martínez, F. (2016), Solubility and apparent specific volume of some pharmaceutical salts in propylene glycol + water mixtures at 298.15 K, Chemical and. Engineering Communications, 203, 1013–1019.
Jouyban, A. (2010), Handbook of Solubility Data for Pharmaceuticals, CRC Press, Boca Raton (FL).
Jouyban, A. (2019), Review of the cosolvency models for predicting solubility in solvent mixtures: An update. Journal of Pharmacy and Pharmaceutical Sciences, 22, 466–485.
Jouyban, A.; Acree, W.E., Jr. (2018), Mathematical derivation of the Jouyban-Acree model to represent solute solubility data in mixed solvents at various temperatures, Journal of Molecular Liquids, 256, 541–547.
Jouyban, A.; Chan, H.-K.; Chew, N.Y.K.; Khoubnasabjafari, M.; Acree, W.E., Jr. (2006), Solubility prediction of paracetamol in binary and ternary solvent mixtures using Jouyban-Acree model, Chemical and Pharmaceutical Bulletin (Tokyo), 54, 428–431.
Jouyban, A.; Khoubnasabjafari, M.; Chan, H.K.; Acree, W.E., Jr. (2006), Mathematical representation of solubility of amino acids in binary aqueous-organic solvent mixtures at various temperatures using the Jouyban-Acree model, Pharmazie, 61, 789–792.
Jouyban, A.; Azarmir, O.; Mirzaei, S.; Hassanzadeh, D.; Ghafourian, T.; Acree, W.E., Jr.; Nokhodchi, A. (2008), Solubility prediction of paracetamol in water-ethanol-propylene glycol mixtures at 25 and 30 degrees C using practical approaches, Chemical and Pharmaceutical Bulletin (Tokyo), 56, 602–606.
Jouyban, A.; Fakhree, M.A.A.; Mirzaei, S.; Ghafourian, T.; Soltanpour, S.; Nokhodchi, A. (2009), Solubility prediction of paracetamol in water-glycerol mixtures at 25 and 30 ºC using the Jouyban-Acree model, Asian Journal of Chemistry, 21, 7249–7253.
Jouyban, A.; Soltanpour, S.; Acree, W.E., Jr. (2010), Solubility of acetaminophen and ibuprofen in the mixtures of polyethylene glycol 200 or 400 with ethanol and water and the density of solute-free mixed solvents at 298.2 K, Journal of Chemical and Engineering Data, 55, 5252–5257.
Jouyban-Gharamaleki, A.; Valaee, L.; Barzegar-Jalali, M.; Clark, B.J.; Acree, W.E., Jr. (1999), Comparison of various cosolvency models for calculating solute solubility in water-cosolvent mixtures, International Journal of Pharmaceutics, 177, 93–101.
Kratky O, Leopold H, Stabinger H. (1980), DMA45 calculating digital density meter, instruction manual, Anton Paar, K.G., Graz, Austria, pp. 1–12.
Krause, G.M.; Cross, J.M. (1951), Solubility of phenobarbital in alcohol-glycerin-water systems, Journal of the American Pharmaceutical Association, Scientific Edition, 40, 137–139.
Kristl, A.; Vesnaver, G. (1995), Thermodynamic investigation of the effect of octanol–water mutual miscibility on the partitioning and solubility of some guanine derivatives, Journal of the Chemical Society, Faraday Transactions, 91, 995–998.
Krug, R.R.; Hunter, W.G.; Grieger, R.A. (1976), Enthalpy-entropy compensation. 2. Separation of the chemical from the statistical effects, Journal of Physical Chemistry, 80, 2341–2351.
Marcus, Y. (1998), The Properties of Solvents, John Wiley & Sons, Chichester (UK).
Marcus, Y. (2002), Solvent Mixtures: Properties and Selective Solvation, Marcel Dekker, Inc., New York, 2002.
Martin, A.; Bustamante, P.; Chun, A.H.C. (1993), Physical Pharmacy: Physical Chemical Principles in the Pharmaceutical Sciences, 4th ed., Lea & Febiger, Philadelphia (PA).
Martínez, F.; Rojas, J.H. (1999), Un método refracto-densimétrico para el análisis de mezclas líquidas ternarias homogéneas, Revista Colombiana de Ciencias Químico Farmacéuticas, 28, 45–51.
Martinez, F.; Jouyban, A.; Acree, W.E., Jr. (2017), Pharmaceuticals solubility is still nowadays widely studied everywhere (Editorial), Pharmaceutical Sciences (Tabriz), 23, 1–2.
Mehrdad, A.; Miri, A.H. (2016), Aqueous solubility of acetaminophen in the presence of 1-hexyl-3-methyl imidazolium bromide, ionic liquid as co-solvent, Fluid Phase Equilibria, 425, 51–56.
Minsalud, Ministerio de Salud de la República de Colombia (2015), Listado vigente de registros de acetaminofén en Colombia – INVIMA - Bogotá, enero 2015, URL: https://www.minsalud.gov.co/Documents/Archivos-temporal-jd/Listado-registros-acetaminofen-colombia-enero-2015.pdf.
Mora, C.P.; Martínez, F. (2006), Thermodynamic quantities relative to solution processes of naproxen in aqueous media at pH 1.2 and 7.4, Physics and Chemistry of Liquids, 44, 585–596.
Muñoz, M.M.; Rodríguez, C.J.; Delgado, D.R.; Peña, M.Á.; Jouyban, A.; Martínez, F. (2015), Solubility and saturation apparent specific volume of some sodium sulfonamides in propylene glycol + water mixtures at 298.15 K, Journal of Molecular Liquids, 211, 192–196.
Muñoz, M.M.; Jouyban, A.; Martínez, F. (2016a), Solubility and preferential solvation of acetaminophen in methanol + water mixtures at 298.15 K, Physics and Chemistry of Liquids, 54, 515–528.
Muñoz, M.M.; Almanza, O.A.; Peña, M.Á.; Jouyban, A.; Martínez, F.; Acree, W.E., Jr. (2016b), Solubility and apparent specific volume at saturation of some pharmaceutical salts in methanol + water mixtures at 298.15 K, Journal of Molecular Liquids, 220, 842–847.
Muñoz, M.M.; Romdhani, A.; Martínez, F.; Jouyban, A.; Acree, W.E., Jr. (2020), Study of some volumetric properties of {ethanol (1) + propylene glycol (2) + water (3)} mixtures at several temperatures, Physics and Chemistry of Liquids, 58, 105–115.
Muthuselvi, C., Archana, E., Ponlakshmi, G., Pandiarajan S. (2016), XRD and spectroscopy analyzes of 4-acetamidophenol grown by single diffusion gel method, Der Chemica Sinica, 7(1), 47-53.
OGA-UNC (2016), Manual para la Gestión Integral de Residuos Generados en la Atención de Salud y otras Actividades, Oficina de Gestión Ambiental, Universidad Nacional de Colombia, Sede Bogotá.
Osorio, I.P.; Martínez, F.; Delgado, D.R.; Jouyban, A.; Acree, W.E., Jr. (2020), Solubility of sulfacetamide in aqueous propylene glycol mixtures: Measurement, correlation, dissolution thermodynamics, preferential solvation and solute volumetric contribution at saturation, Journal of Molecular Liquids, 297, 111889.
Palatnik, L.S.; Landau, A.I. (1965), Phase Equilibria in Multicomponent Systems, Holt, Rinehart and Wilson, Inc., New York (NY).
Paruta, A.N.; Irani, S.A. (1965), Dielectric solubility profiles in dioxane-water mixtures for several antipyretic drugs. Effect of substituents, Journal of Pharmaceutical Sciences, 54, 1334-1338.
Pérez, D.C. (2003), Volúmenes de desplazamiento de acetaminofén en mezclas agua-etanol a 25 °C, Trabajo de Grado, Carrera de Farmacia, Universidad Nacional de Colombia, Bogotá, D.C.
Pérez, D.C.; Guevara, C.C.; Cárdenas, C.A.; Pinzón, J.A.; Barbosa, H.J.; Martínez, F. (2003), Solubilidad y volúmenes de desplazamiento del acetaminofén en mezclas binarias formadas por agua, etanol y propilenoglicol a 25.0 °C, Revista Colombiana de Ciencias Químico Farmacéuticas, 32, 116–136.
Perlovich, G.L.; Kurkov, S.V.; Bauer-Brandl, A. (2003), Thermodynamics of solutions II: Flurbiprofen and diflunisal as models for studying solvation of drug substances, European Journal of Pharmaceutical Sciences, 19, 423–432.
Perlovich, G.L.; Kurkov, S.V.; Kinchin, A.N.; Bauer-Brandl, A. (2004), Thermodynamics of solutions III: comparison of the solvation of (+)-naproxen with other NSAIDs, European Journal of Pharmaceutics and Biopharmaceutics, 57, 411–420.
Perlovich, G.L.; Volkova, T.V.; Bauer-Brandl, A. (2006), Towards an understanding of the molecular mechanism of solvation of drug molecules: A thermodynamic approach by crystal lattice energy, sublimation, and solubility exemplified by paracetamol, acetanilide, and phenacetin, Journal of Pharmaceutical Sciences, 95, 2158–2169.
Peterson, C.F.; Hopponen, R.E. (1953), Solubility of phenobarbital in propylene glycol-alcohol-water systems, Journal of the American Pharmaceutical Association, Scientific Edition, 42, 540–542.
Pourkarim, F.; Mirheydari, S.N.; Martinez, F.; Jouyban, A. (2020), Solubility of acetaminophen in 1-propanol + water mixtures at T= (293.2 to 313.2) K, Physics and Chemistry of Liquids, 58, 456–472.
Prakongpan, S.; Nagai, T. (1984), Solubility of acetaminophen in cosolvents, Chemical and Pharmaceutical Bulletin (Tokyo), 32, 340–343.
Raffa, R.B. (2005), Analgesic, antipyretic, and anti-inflammatory drugs, in: Gennaro, A. (editor), Remington: The Science and Practice of Pharmacy, 21st ed., Lippincott Williams & Wilkins, Philadelphia (PA), pp. 1524–1542.
Rahimpour, E.; Agha, E.M.H.; Martinez, F.; Barzegar-Jalali, M.; Jouyban, A. (2021), Solubility study of acetaminophen in the mixtures of acetonitrile and water at different temperatures, Journal of Molecular Liquids, 324, 114708.
Roberts, L.J., II; Morrow, J.D. (2001), Analgesic, antipyretic and anti-inflammatory agents and drugs employed in the treatment of gout, in: Hardman, J.G. Limbird, L.E. Gilman, A.G. (editor), Goodman & Gilman’s: The Pharmacological Basis of Therapeutics, 10th ed., McGraw-Hill, New York (NY), chapter 27.
Romdhani, A.; Martínez, F.; Almanza, O.A.; Peña, M.A.; Jouyban, A.; Acree, W.E., Jr. (2019), Solubility of sulfacetamide in (ethanol + water) mixtures: Measurement, correlation, thermodynamics, preferential solvation and volumetric contribution at saturation, Journal of Molecular Liquids, 290, 111219.
Romero, S.; Reillo, A.; Escalera, B.; Bustamante, P. (1996), The behavior of paracetamol in mixtures of amphiprotic and amphiprotic-aprotic solvents: Relationship of solubility curves to specific and nonspecific interactions, Chemical and Pharmaceutical Bulletin (Tokyo), 44, 1061–1064.
Romero, S.; Bustamante, P.; Escalera, B.; Cirri, M.; Mura, P. (2004), Characterization of the solid phases of paracetamol and fenamates at equilibrium in saturated solutions, Journal of Thermal Analysis and Calorimetry, 77, 541–554.
Rowe, R.C.; Sheskey, P.J.; Quinn, M.E. (editors) (2009), Handbook of Pharmaceutical Excipients, 6th ed., Pharmaceutical Press, London.
Rubino, J.T. (1988), Cosolvents and cosolvency, in: Swarbrick, J., Boylan, J.C. (editors), Encyclopedia of Pharmaceutical Technology, vol. 3, Marcel Dekker, Inc., New York (NY), pp. 375–398.
Ruidiaz, M.A.; Delgado, D.R.; Martínez, F.; Marcus, Y. (2010), Solubility and preferential solvation of indomethacin in 1,4-dioxane + water solvent mixtures, Fluid Phase Equilibria, 299, 259–265.
Sestili, P.; Fimognari, C. (2020), Paracetamol-induced glutathione consumption: Is there a link with severe COVID-19 illness? Frontiers in Pharmacology, 11, 579944.
Sheth, B.; Paruta A.N.; Niger, R. (1966), Solubility of acetanilide and several derivatives in sucrose solution, Journal of Pharmaceutical Sciences, 55, 1144-1147.
Soltanpour, S.; Jouyban, A. (2010), Solubility of acetaminophen and ibuprofen in binary and ternary mixtures of polyethylene glycol 600, ethanol and water, Chemical and Pharmaceutical Bulletin (Tokyo), 58, 219–224.
Sweetman, S.C. (editor) (2009), Martindale: The Complete Drug Reference, 36th ed., Pharmaceutical Press, London.
Tinjacá, D.A.; Muñoz, M.M.; Jouyban, A.; Martínez, F.; Acree, W.E., Jr. (2019), Equilibrium solubility, preferential solvation and apparent specific volume of sucrose in some {cosolvent (1) + water (2)} mixtures at 298.2 K, Physics and Chemistry of Liquids, 57, 259–273.
Tinjacá, D.A.; Muñoz, M.M.; Rahimpour, E.; Jouyban, A.; Martínez, F.; Acree, W.E., Jr. (2018), Solubility and apparent specific volume of sucrose in some aqueous polyethylene glycol mixtures at 298.2 K, Pharmaceutical Sciences (Tabriz), 24, 163–167.
Trissel, L.A. (editor) (2013), Handbook on Injectable Drugs, 17th ed., American Society of Health-System Pharmacists, Bethesda (MD).
Tsapatsaris, N.; Kolesov, B.A.; Fischer, J.; Boldyreva, E.V.; Daemen, L.; Eckert, J.; Bordallo, H.N. (2014), Polymorphism of paracetamol: A new understanding of molecular flexibility through local methyl dynamics, Molecular Pharmaceutics, 11, 1032–1041.
Yalkowsky, S.H. (1999), Solubility and Solubilization in Aqueous Media, American Chemical Society and Oxford University Press, New York (NY), pp. 91–134.
Yoshioka, S.; Stella, V.J. (2002), Stability of Drugs and Dosage Forms, Kluwer Academic Publishers, New York (NY).
Yurquina, A.; Manzur, M.E.; Brito, P.; Manzo, R.; Molina, M.A.A. (2007), Physicochemical studies of acetaminophen in water-PEG 400 systems, Journal of Molecular Liquids, 133, 47–53.
Zadali-Asghar, S.; Jouyban, A.; Martinez, F.; Rahimpour, E. (2018), Solubility of naproxen in ternary mixtures of {ethanol + propylene glycol + water} at various temperatures: Data correlation and thermodynamic analysis, Journal of Molecular Liquids, 268, 517–522.
dc.rights.spa.fl_str_mv Derechos reservados al autor, 2022
dc.rights.coar.fl_str_mv http://purl.org/coar/access_right/c_abf2
dc.rights.license.spa.fl_str_mv Reconocimiento 4.0 Internacional
dc.rights.uri.spa.fl_str_mv http://creativecommons.org/licenses/by/4.0/
dc.rights.accessrights.spa.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv Reconocimiento 4.0 Internacional
Derechos reservados al autor, 2022
http://creativecommons.org/licenses/by/4.0/
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.extent.spa.fl_str_mv xviii, 82 páginas
dc.format.mimetype.spa.fl_str_mv application/pdf
dc.publisher.spa.fl_str_mv Universidad Nacional de Colombia
dc.publisher.program.spa.fl_str_mv Bogotá - Ciencias - Maestría en Ciencias Farmacéuticas
dc.publisher.faculty.spa.fl_str_mv Facultad de Ciencias
dc.publisher.place.spa.fl_str_mv Bogotá, Colombia
dc.publisher.branch.spa.fl_str_mv Universidad Nacional de Colombia - Sede Bogotá
institution Universidad Nacional de Colombia
bitstream.url.fl_str_mv https://repositorio.unal.edu.co/bitstream/unal/82880/1/license.txt
https://repositorio.unal.edu.co/bitstream/unal/82880/2/461291.2022.pdf
https://repositorio.unal.edu.co/bitstream/unal/82880/3/461291.2022.pdf.jpg
bitstream.checksum.fl_str_mv eb34b1cf90b7e1103fc9dfd26be24b4a
8a3129a78076eb40f2bf4a4495eb7142
fe9355f1c3c32360d2168441dfed7f4c
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
MD5
repository.name.fl_str_mv Repositorio Institucional Universidad Nacional de Colombia
repository.mail.fl_str_mv repositorio_nal@unal.edu.co
_version_ 1814089545366372352
spelling Reconocimiento 4.0 InternacionalDerechos reservados al autor, 2022http://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Martínez Rodríguez, Fleming59595ca65dfb3c1612425d7ede691a3cRomdhani, Asma7b03c687051b5b05459dd59694748219Grupo de Investigaciones Farmacéutico-FisicoquímicasRomdhani, Asma [https://scienti.minciencias.gov.co/cvlac/visualizador/generarCurriculoCv.do?cod_rh=0000117660]Romdhani, Asma [https://www-scopus-com.ezproxy.unal.edu.co/authid/detail.uri?origin=resultslist&authorId=54901767600&zone=]Romdhani, Asma [https://www.researchgate.net/profile/Asma-Romdhani]Romdhani, Asma [https://scholar.google.com/citations?user=gKs1hk0AAAAJ]2023-01-11T19:53:01Z2023-01-11T19:53:01Z2022-08https://repositorio.unal.edu.co/handle/unal/82880Universidad Nacional de ColombiaRepositorio Institucional Universidad Nacional de Colombiahttps://repositorio.unal.edu.co/ilustraciones, gráficas, tablasThe equilibrium solubility of acetaminophen (ACP) was determined at five temperatures from (293.15 to 313.15) K in {ethanol (EtOH) (1) + propylene glycol (PG) (2) + water (3)} ternary mixtures. From the variation of solubility with temperature, the apparent thermodynamic analysis of dissolution was carried out in all the ternary mixtures. Additionally, the thermodynamic quantities of mixing and solvation were also calculated, as well as the apparent specific volume at saturation of ACP. The solubility of ACP expressed in mole fraction (x4) increases with temperature-increasing and also increases with proportion-increasing of EtOH and/or PG. It varies from x4 = 4.56 × 10–3 in the mixture of 0.10-0.10-0.80 (in mass fraction) to x4 = 6.63 × 10–2 in the mixture of 0.80-0.10-0.10 at 298.15 K. The solubility behavior was well correlated using the Jouyban-Acree model obtaining mean percentage deviations (MPD) of 4.0% (N=330).Se determinó la solubilidad en equilibrio de acetaminofeno (ACF) a cinco temperaturas desde (293,15 hasta 313,15) K en mezclas ternarias {etanol (EtOH) (1) + propilenglicol (PG) (2) + agua (3)}. A partir de la variación de la solubilidad con la temperatura se realizó el análisis termodinámico aparente de disolución en todas las mezclas ternarias. Adicionalmente se calcularon las cantidades termodinámicas de mezcla y solvatación, así como el volumen específico aparente a saturación de ACF. La solubilidad de ACF expresada en fracción molar (x4) aumenta al incrementar la temperatura y también aumenta con el incremento en las proporciones de EtOH y/o PG. Esta varía desde x4 = 4,56 × 10–3 en la mezcla 0,10-0,10-0,80 (en fracción de masa) hasta x4 = 6,63 × 10–2 en la mezcla 0,80-0,10-0,10 a 298,15 K. El comportamiento de solubilidad se correlacionó adecuadamente mediante el modelo de Jouyban-Acree obteniendo desviaciones porcentuales medias (MPD) del 4,0% (N=330).MaestríaMagíster en Ciencias FarmacéuticasFarmacotecniaxviii, 82 páginasapplication/pdfengUniversidad Nacional de ColombiaBogotá - Ciencias - Maestría en Ciencias FarmacéuticasFacultad de CienciasBogotá, ColombiaUniversidad Nacional de Colombia - Sede Bogotá610 - Medicina y salud::615 - Farmacología y terapéuticaTermoquímicaEnsayo de acetaminofénThermochemistryAcetaminophen AssayAcetaminophen(Ethanol + propylene glycol + water) mixturesSolubilityJouyban-Acree modelDissolution thermodynamicsApparent specific volumeAcetaminofenoMezclas (etanol + propilenglicol + agua)SolubilidadModelo de Jouyban-AcreeTermodinámica de disoluciónVolumen específico aparenteSolubility and solution thermodynamics of acetaminophen in (ethanol + propylene glycol + water) ternary mixturesSolubilidad y termodinámica de disolución de acetaminofeno en mezclas ternarias (etanol + propilenglicol + agua)Trabajo de grado - Maestríainfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/acceptedVersionTexthttp://purl.org/redcol/resource_type/TMAgostinho, D.A.S.; Jesus, A.R.; Silva, A.B.P.; Esperança, J.M.S.S.; Paiva, A.; Duarte, A.R.C.; Reis, P.M. (2021), Improvement of new dianionic ionic liquids vs monoanionic in solubility of poorly water-soluble drugs, Journal of Pharmaceutical Sciences, 110, 2489–2500.Ahumada, E.A. (2012), Estudio fisicoquímico de la solubilidad de acetaminofeno en mezclas polietilenglicol 400 + agua, Tesis de Maestría en Ciencias Farmacéuticas Universidad Nacional de Colombia, Bogotá D.C.Ahumada, E.A.; Delgado, D.R.; Martínez, F. (2012a), Solution thermodynamics of acetaminophen in some PEG 400 + water mixtures, Fluid Phase Equilibria, 332, 120–127.Ahumada, E.A.; Delgado, D.R.; Martínez, F. (2012b), Corrigendum to “Solution thermodynamics of acetaminophen in some PEG 400 + water mixtures” [Fluid Phase Equilibr. 332 (2012) 120–127], Fluid Phase Equilibria, 334, 204.Aulton, M.E. (2002), Pharmaceutics: The Science of Dosage Forms Design, 2nd ed., Churchill Livingstone, London.Avdeef, A. (2003), Absorption and Drug Development, Solubility, Permeability and Charge State, Wiley-Interscience, Hoboken (NJ).Baena, Y.; Pinzón, J.A.; Barbosa, H.; Martínez, F. (2004), Temperature dependence of the solubility of some acetanilide derivatives in several organic and aqueous solvents, Physics and Chemistry of Liquids, 42, 603–613.Barrante, J.R. (2003), Applied Mathematics for Physical Chemistry, 3rd ed., Prentice Hall, Upper Saddle River (NJ).Barton, A.F.M. (1991), Handbook of Solubility Parameters and Other Cohesion Parameters, 2nd ed., CRC Press, Boca Raton (FL).Bashpa, P.; Bijudas, K.; Tom, A.M.; Archana, P.K.; Murshida, K.P.; Noufala-Banu, K.; Amritha, K.R.; Vimisha, K. (2014), Polymorphism of paracetamol: A comparative study on commercial paracetamol samples, International Journal of Chemical Studies, 1, 25–29.Bevington, P.R.; Robinson, D.K. (2003), Data Reduction and Error Analysis for the Physical Sciences, 3rd ed., McGraw-Hill Education, Co., New York (NY), pp. 36–49.Blanco, L.H. (2010), Plan de Gestión Integral de Residuos o Desechos Peligrosos de la Universidad Nacional de Colombia –Sede Bogotá (RESPEL), Facultad de Ingeniería, Universidad Nacional de Colombia, Bogotá.Bolaños, C.I.; Erazo, E.A.; Luengas, P.; Barbosa, H.; Martínez, F. (1999), Solubilidad de acetaminofén en los sistemas agua-alcohol USP-jarabe USP y agua-alcohol USP-sorbitol USP, Revista Colombiana de Ciencias Químico Farmacéuticas, 28, 71–75.Budavari, S.; O’Neil, M.J.; Smith, A.; Heckelman, P.E., Obenchain, J.R., Jr.; Gallipeau, J.A.R.; D’Arecea, M.A. (editors) (2001), The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 13th ed., Merck & Co., Inc., Whitehouse Station (NJ).Bustamante, P.; Romero, S.; Reillo, A. (1995), Thermodynamics of paracetamol in amphiprotic and amphiprotic-aprotic solvent mixtures, Pharmacy and Pharmacology Communications, 1, 505–507.Bustamante, P.; Romero, S.; Peña, A.; Escalera, B.; Reillo, A. (1998), Nonlinear enthalpy-entropy compensation for the solubility of drugs in solvent mixtures: paracetamol, acetanilide and nalidixic acid in dioxane-water, Journal of Pharmaceutical Sciences, 87, 1590–1596.Cárdenas, C.A., Guevara, C.C. (2003), Solubilidad y volúmenes de desplazamiento del acetaminofén en mezclas agua-propilenoglicol y etanol-propilenoglicol a 25 °C, Trabajo de Grado, Carrera de Farmacia, Universidad Nacional de Colombia, Bogotá D.C.Cárdenas, Z.J.; Jiménez, D.M.; Martínez, F. (2015), Solubility and saturation apparent volume of propranolol.HCl in some binary aqueous cosolvent mixtures at 298.15 K, Journal of Chemical and Engineering Data, 60, 1520–1525.Carstensen, J.T. (1996), Modeling and data treatment in the pharmaceutical sciences, Technomic Publishing Co., Inc., Lancaster (PA), 127–159.Chirumbolo, S. (2021), Paracetamol in the home treatment of early COVID‐19 symptoms: A possible foe rather than a friend for elderly patients? Journal of Medical Virology, 93, 5704–5706.Connors, K.A. (2002), Thermodynamics of Pharmaceutical Systems: An Introduction for Students of Pharmacy, Wiley–Interscience, Hoboken (NJ).Connors, K.A.; Amidon, G.L.; Stella, V.J. (1986), Chemical Stability of Pharmaceuticals: A Handbook for Pharmacists, 2nd ed., John Wiley & Sons, New York (NY).Coronado, Y.P.; Fonseca, J.C.; Luengas, P.E.; Barbosa, H.J.; Martínez, F. (1999), Solubilidad de acetaminofén en sistemas solventes agua-alcohol-poliol, Revista Colombiana de Ciencias Químico Farmacéuticas, 28, 59–63.Crighton, A.J.; McCann, C.T.; Todd, E.J.; Brown, A.J. (2020), Safe use of paracetamol and high-dose NSAID analgesia in dentistry during the COVID-19 pandemic, British Dental Journal, 229(1), 15–18.Delgado, D.R.; Martinez, F. (2013a), Solution thermodynamics of sulfadiazine in ethanol + water mixtures, Journal of Molecular Liquids, 187, 99–105.Delgado, D.R.; Martínez, F. (2013b), Solubility and solution thermodynamics of sulfamerazine and sulfamethazine in some ethanol + water mixtures, Fluid Phase Equilibria, 360, 88–96.Delgado, D.R.; Rodríguez, G.A.; Martínez, F. (2013), Thermodynamic study of the solubility of sulfapyridine in some ethanol + water mixtures, Journal of Molecular Liquids, 177, 156–161.Delgado, D.R.; Almanza, O.A.; Martínez, F.; Peña, M.A.; Jouyban, A.; Acree, W.E., Jr. (2016), Solution thermodynamics and preferential solvation of sulfamethazine in (methanol + water) mixtures, Journal of Chemical Thermodynamics, 97, 264–276.Echeverry, L.C.; Muñoz, M.M.; Tinjacá, D.A.; Martinez, F.; Peña, M.A.; Rahimpour, E.; Jouyban, A.; Acree, W.E., Jr. (2019), Equilibrium solubility and apparent specific volume of lidocaine.HCl.H2O in some {cosolvent (1) + water (2)} mixtures at 298.2 K, Physics and Chemistry of Liquids, 57, 679–688.Espeau, P.; Céolin, R.; Tamarit, J.L.; Perrin, M.A.; Gauchi, J.P.; Leveiller, F. (2005), Polymorphism of paracetamol: Relative stabilities of the monoclinic and orthorhombic phases inferred from topological pressure-temperature and temperature-volume phase diagrams, Journal of Pharmaceutical Sciences, 94, 524–539.Etman, M.A.; Naggar, V.F. (1990), Thermodynamics of paracetamol solubility in sugar-water cosolvent systems, International Journal of Pharmaceutics, 58, 177–184.Faroongsarng, D., Kadejinda, W., Sunthornpit, A. (2000), Thermal behavior of a pharmaceutical solid acetaminophen doped with p-aminophenol, AAPS PharmSciTech, 1(3), article 23.Fedors, R.F. (1974), A method for estimating both the solubility parameters and molar volumes of liquids, Polymer Engineering and Science, 14, 147–154.Ferro, V.; Ávila, P. (1986), Perfiles de solubilidad en diferentes sistemas solventes para algunos derivados de la anilina con acción antipirética-analgésica, Tesis de Grado, Departamento de Farmacia, Universidad Nacional de Colombia, Bogotá D.E.Florence, A.T.; Attwood, D. (2006), Physicochemical Principles of Pharmacy, 4th ed., Pharmaceutical Press, London.Fonseca, J.C.; Coronado, Y.P. (1998), Determinación de la solubilidad de acetaminofén en sistemas ternarios. Parte II. Sistemas agua-alcohol-poliol, Tesis de Grado, Carrera de Farmacia, Universidad Nacional de Colombia, Santafé de Bogotá, D.C.Grant, D.J.W.; Mehdizadeh, M., Chow, A.H.L.; Fairbrother, J.E. (1984), Nonlinear van’t Hoff solubility-temperature plots and their pharmaceutical interpretation, International Journal of Pharmaceutics, 18, 25–38.Hamza, Y.E.; Paruta, A.N. (1985), Solubilization of paracetamol using nonionic surfactants and cosolubilizers, Drug Development and Industrial Pharmacy, 11, 187-206.Hatefi, A.; Jouyban, A.; Mohammadian, E., Acree, W.E., Jr.; Rahimpour, E. (2019), Prediction of paracetamol solubility in cosolvency systems at different temperatures, Journal of Molecular Liquids, 273, 282–291.Jendrzejewska, I., Goryczka, T., Pietrasik, E., Klimontko, J., Jampilek, J. (2020), X-ray and thermal analysis of selected drugs containing acetaminophen, Molecules, 25, 5909.Jesus, A.R.; Soromenho, M.R.C.; Raposo, L.R.; Esperança, J.M.S.S.; Baptista, P.V.; Fernandes, A.R.; Reis, P.M. (2019), Enhancement of water solubility of poorly water-soluble drugs by new biocompatible N-acetyl amino acid N-alkyl cholinium-based ionic liquids, European Journal of Pharmaceutics and Biopharmaceutics, 137, 227–232.Jesus, A.R.; Raposo, L.R.; Soromenho, M.R.C.; Agostinho, D.A.S.; Esperança, J.M.S.S.; Baptista, P.V.; Fernandes, A.R.; Reis, P.M. (2021), New non-toxic N-alkyl cholinium-based ionic liquids as excipients to improve the solubility of poorly water-soluble drugs, Symmetry, 13, 2053.Jiménez, J.A. (2005), Solubilidad de acetaminofén en mezclas binarias cosolventes formadas por agua, etanol y propilenoglicol en función de la temperatura, Trabajo de Grado, Departamento de Farmacia, Universidad Nacional de Colombia, Bogotá D.C.Jiménez, F.; Martínez, F. (1995), Una estrategia para la selección sistemática de vehículos en el diseño de formas farmacéuticas liquidas homogéneas, Revista Colombiana de Ciencias Químico Farmacéuticas, 24, 19–23.Jiménez, J.; Martínez, F. (2005a), Study of some volumetric properties of 1,2-propanediol + water mixtures at several temperatures, Revista Colombiana de Ciencias Químico Farmacéuticas, 34, 46–57.Jiménez, J.A.; Martínez, F. (2005b), Thermodynamic magnitudes of mixing and solvation of acetaminophen in ethanol + water cosolvent mixtures, Revista de la Academia Colombiana de Ciencias, 30, 87–99.Jiménez, J.; Martínez, F. (2006a), Volumetric properties of ethanol + 1,2-propanediol mixtures at different temperatures, Physics and Chemistry of Liquids, 44, 521–530.Jiménez, J.A.; Martínez, F. (2006b), Temperature dependence of solubility of acetaminophen in propylene glycol + ethanol mixtures, Journal of Solution Chemistry, 35, 335–352.Jiménez, J.A.; Martínez, F. (2006c), Thermodynamic study of the solubility of acetaminophen in propylene glycol + water cosolvent mixtures, Journal of the Brazilian Chemical Society, 17, 125–134.Jiménez, J.; Manrique, J.; Martínez, F. (2004), Effect of temperature on some volumetric properties for ethanol + water mixtures, Revista Colombiana de Ciencias Químico Farmacéuticas, 33, 145–155.Jiménez, J.A.; Guevara, C.C.; Cárdenas, C.A.; Pérez, D.C.; Barbosa, H.J.; Pinzón, J.A.; Martínez, F. (2005), Solubilidad y volúmenes de desplazamiento de algunos analgésicos en mezclas cosolventes a 25.0 °C, Proyecto de Investigación No 1.540 de 2003, Fundación para la Promoción de la Investigación y la Tecnología, Banco de la República, Bogotá D.C.Jiménez, D.M.; Cárdenas, Z.J.; Martínez, F. (2016), Solubility and apparent specific volume of some pharmaceutical salts in propylene glycol + water mixtures at 298.15 K, Chemical and. Engineering Communications, 203, 1013–1019.Jouyban, A. (2010), Handbook of Solubility Data for Pharmaceuticals, CRC Press, Boca Raton (FL).Jouyban, A. (2019), Review of the cosolvency models for predicting solubility in solvent mixtures: An update. Journal of Pharmacy and Pharmaceutical Sciences, 22, 466–485.Jouyban, A.; Acree, W.E., Jr. (2018), Mathematical derivation of the Jouyban-Acree model to represent solute solubility data in mixed solvents at various temperatures, Journal of Molecular Liquids, 256, 541–547.Jouyban, A.; Chan, H.-K.; Chew, N.Y.K.; Khoubnasabjafari, M.; Acree, W.E., Jr. (2006), Solubility prediction of paracetamol in binary and ternary solvent mixtures using Jouyban-Acree model, Chemical and Pharmaceutical Bulletin (Tokyo), 54, 428–431.Jouyban, A.; Khoubnasabjafari, M.; Chan, H.K.; Acree, W.E., Jr. (2006), Mathematical representation of solubility of amino acids in binary aqueous-organic solvent mixtures at various temperatures using the Jouyban-Acree model, Pharmazie, 61, 789–792.Jouyban, A.; Azarmir, O.; Mirzaei, S.; Hassanzadeh, D.; Ghafourian, T.; Acree, W.E., Jr.; Nokhodchi, A. (2008), Solubility prediction of paracetamol in water-ethanol-propylene glycol mixtures at 25 and 30 degrees C using practical approaches, Chemical and Pharmaceutical Bulletin (Tokyo), 56, 602–606.Jouyban, A.; Fakhree, M.A.A.; Mirzaei, S.; Ghafourian, T.; Soltanpour, S.; Nokhodchi, A. (2009), Solubility prediction of paracetamol in water-glycerol mixtures at 25 and 30 ºC using the Jouyban-Acree model, Asian Journal of Chemistry, 21, 7249–7253.Jouyban, A.; Soltanpour, S.; Acree, W.E., Jr. (2010), Solubility of acetaminophen and ibuprofen in the mixtures of polyethylene glycol 200 or 400 with ethanol and water and the density of solute-free mixed solvents at 298.2 K, Journal of Chemical and Engineering Data, 55, 5252–5257.Jouyban-Gharamaleki, A.; Valaee, L.; Barzegar-Jalali, M.; Clark, B.J.; Acree, W.E., Jr. (1999), Comparison of various cosolvency models for calculating solute solubility in water-cosolvent mixtures, International Journal of Pharmaceutics, 177, 93–101.Kratky O, Leopold H, Stabinger H. (1980), DMA45 calculating digital density meter, instruction manual, Anton Paar, K.G., Graz, Austria, pp. 1–12.Krause, G.M.; Cross, J.M. (1951), Solubility of phenobarbital in alcohol-glycerin-water systems, Journal of the American Pharmaceutical Association, Scientific Edition, 40, 137–139.Kristl, A.; Vesnaver, G. (1995), Thermodynamic investigation of the effect of octanol–water mutual miscibility on the partitioning and solubility of some guanine derivatives, Journal of the Chemical Society, Faraday Transactions, 91, 995–998.Krug, R.R.; Hunter, W.G.; Grieger, R.A. (1976), Enthalpy-entropy compensation. 2. Separation of the chemical from the statistical effects, Journal of Physical Chemistry, 80, 2341–2351.Marcus, Y. (1998), The Properties of Solvents, John Wiley & Sons, Chichester (UK).Marcus, Y. (2002), Solvent Mixtures: Properties and Selective Solvation, Marcel Dekker, Inc., New York, 2002.Martin, A.; Bustamante, P.; Chun, A.H.C. (1993), Physical Pharmacy: Physical Chemical Principles in the Pharmaceutical Sciences, 4th ed., Lea & Febiger, Philadelphia (PA).Martínez, F.; Rojas, J.H. (1999), Un método refracto-densimétrico para el análisis de mezclas líquidas ternarias homogéneas, Revista Colombiana de Ciencias Químico Farmacéuticas, 28, 45–51.Martinez, F.; Jouyban, A.; Acree, W.E., Jr. (2017), Pharmaceuticals solubility is still nowadays widely studied everywhere (Editorial), Pharmaceutical Sciences (Tabriz), 23, 1–2.Mehrdad, A.; Miri, A.H. (2016), Aqueous solubility of acetaminophen in the presence of 1-hexyl-3-methyl imidazolium bromide, ionic liquid as co-solvent, Fluid Phase Equilibria, 425, 51–56.Minsalud, Ministerio de Salud de la República de Colombia (2015), Listado vigente de registros de acetaminofén en Colombia – INVIMA - Bogotá, enero 2015, URL: https://www.minsalud.gov.co/Documents/Archivos-temporal-jd/Listado-registros-acetaminofen-colombia-enero-2015.pdf.Mora, C.P.; Martínez, F. (2006), Thermodynamic quantities relative to solution processes of naproxen in aqueous media at pH 1.2 and 7.4, Physics and Chemistry of Liquids, 44, 585–596.Muñoz, M.M.; Rodríguez, C.J.; Delgado, D.R.; Peña, M.Á.; Jouyban, A.; Martínez, F. (2015), Solubility and saturation apparent specific volume of some sodium sulfonamides in propylene glycol + water mixtures at 298.15 K, Journal of Molecular Liquids, 211, 192–196.Muñoz, M.M.; Jouyban, A.; Martínez, F. (2016a), Solubility and preferential solvation of acetaminophen in methanol + water mixtures at 298.15 K, Physics and Chemistry of Liquids, 54, 515–528.Muñoz, M.M.; Almanza, O.A.; Peña, M.Á.; Jouyban, A.; Martínez, F.; Acree, W.E., Jr. (2016b), Solubility and apparent specific volume at saturation of some pharmaceutical salts in methanol + water mixtures at 298.15 K, Journal of Molecular Liquids, 220, 842–847.Muñoz, M.M.; Romdhani, A.; Martínez, F.; Jouyban, A.; Acree, W.E., Jr. (2020), Study of some volumetric properties of {ethanol (1) + propylene glycol (2) + water (3)} mixtures at several temperatures, Physics and Chemistry of Liquids, 58, 105–115.Muthuselvi, C., Archana, E., Ponlakshmi, G., Pandiarajan S. (2016), XRD and spectroscopy analyzes of 4-acetamidophenol grown by single diffusion gel method, Der Chemica Sinica, 7(1), 47-53.OGA-UNC (2016), Manual para la Gestión Integral de Residuos Generados en la Atención de Salud y otras Actividades, Oficina de Gestión Ambiental, Universidad Nacional de Colombia, Sede Bogotá.Osorio, I.P.; Martínez, F.; Delgado, D.R.; Jouyban, A.; Acree, W.E., Jr. (2020), Solubility of sulfacetamide in aqueous propylene glycol mixtures: Measurement, correlation, dissolution thermodynamics, preferential solvation and solute volumetric contribution at saturation, Journal of Molecular Liquids, 297, 111889.Palatnik, L.S.; Landau, A.I. (1965), Phase Equilibria in Multicomponent Systems, Holt, Rinehart and Wilson, Inc., New York (NY).Paruta, A.N.; Irani, S.A. (1965), Dielectric solubility profiles in dioxane-water mixtures for several antipyretic drugs. Effect of substituents, Journal of Pharmaceutical Sciences, 54, 1334-1338.Pérez, D.C. (2003), Volúmenes de desplazamiento de acetaminofén en mezclas agua-etanol a 25 °C, Trabajo de Grado, Carrera de Farmacia, Universidad Nacional de Colombia, Bogotá, D.C.Pérez, D.C.; Guevara, C.C.; Cárdenas, C.A.; Pinzón, J.A.; Barbosa, H.J.; Martínez, F. (2003), Solubilidad y volúmenes de desplazamiento del acetaminofén en mezclas binarias formadas por agua, etanol y propilenoglicol a 25.0 °C, Revista Colombiana de Ciencias Químico Farmacéuticas, 32, 116–136.Perlovich, G.L.; Kurkov, S.V.; Bauer-Brandl, A. (2003), Thermodynamics of solutions II: Flurbiprofen and diflunisal as models for studying solvation of drug substances, European Journal of Pharmaceutical Sciences, 19, 423–432.Perlovich, G.L.; Kurkov, S.V.; Kinchin, A.N.; Bauer-Brandl, A. (2004), Thermodynamics of solutions III: comparison of the solvation of (+)-naproxen with other NSAIDs, European Journal of Pharmaceutics and Biopharmaceutics, 57, 411–420.Perlovich, G.L.; Volkova, T.V.; Bauer-Brandl, A. (2006), Towards an understanding of the molecular mechanism of solvation of drug molecules: A thermodynamic approach by crystal lattice energy, sublimation, and solubility exemplified by paracetamol, acetanilide, and phenacetin, Journal of Pharmaceutical Sciences, 95, 2158–2169.Peterson, C.F.; Hopponen, R.E. (1953), Solubility of phenobarbital in propylene glycol-alcohol-water systems, Journal of the American Pharmaceutical Association, Scientific Edition, 42, 540–542.Pourkarim, F.; Mirheydari, S.N.; Martinez, F.; Jouyban, A. (2020), Solubility of acetaminophen in 1-propanol + water mixtures at T= (293.2 to 313.2) K, Physics and Chemistry of Liquids, 58, 456–472.Prakongpan, S.; Nagai, T. (1984), Solubility of acetaminophen in cosolvents, Chemical and Pharmaceutical Bulletin (Tokyo), 32, 340–343.Raffa, R.B. (2005), Analgesic, antipyretic, and anti-inflammatory drugs, in: Gennaro, A. (editor), Remington: The Science and Practice of Pharmacy, 21st ed., Lippincott Williams & Wilkins, Philadelphia (PA), pp. 1524–1542.Rahimpour, E.; Agha, E.M.H.; Martinez, F.; Barzegar-Jalali, M.; Jouyban, A. (2021), Solubility study of acetaminophen in the mixtures of acetonitrile and water at different temperatures, Journal of Molecular Liquids, 324, 114708.Roberts, L.J., II; Morrow, J.D. (2001), Analgesic, antipyretic and anti-inflammatory agents and drugs employed in the treatment of gout, in: Hardman, J.G. Limbird, L.E. Gilman, A.G. (editor), Goodman & Gilman’s: The Pharmacological Basis of Therapeutics, 10th ed., McGraw-Hill, New York (NY), chapter 27.Romdhani, A.; Martínez, F.; Almanza, O.A.; Peña, M.A.; Jouyban, A.; Acree, W.E., Jr. (2019), Solubility of sulfacetamide in (ethanol + water) mixtures: Measurement, correlation, thermodynamics, preferential solvation and volumetric contribution at saturation, Journal of Molecular Liquids, 290, 111219.Romero, S.; Reillo, A.; Escalera, B.; Bustamante, P. (1996), The behavior of paracetamol in mixtures of amphiprotic and amphiprotic-aprotic solvents: Relationship of solubility curves to specific and nonspecific interactions, Chemical and Pharmaceutical Bulletin (Tokyo), 44, 1061–1064.Romero, S.; Bustamante, P.; Escalera, B.; Cirri, M.; Mura, P. (2004), Characterization of the solid phases of paracetamol and fenamates at equilibrium in saturated solutions, Journal of Thermal Analysis and Calorimetry, 77, 541–554.Rowe, R.C.; Sheskey, P.J.; Quinn, M.E. (editors) (2009), Handbook of Pharmaceutical Excipients, 6th ed., Pharmaceutical Press, London.Rubino, J.T. (1988), Cosolvents and cosolvency, in: Swarbrick, J., Boylan, J.C. (editors), Encyclopedia of Pharmaceutical Technology, vol. 3, Marcel Dekker, Inc., New York (NY), pp. 375–398.Ruidiaz, M.A.; Delgado, D.R.; Martínez, F.; Marcus, Y. (2010), Solubility and preferential solvation of indomethacin in 1,4-dioxane + water solvent mixtures, Fluid Phase Equilibria, 299, 259–265.Sestili, P.; Fimognari, C. (2020), Paracetamol-induced glutathione consumption: Is there a link with severe COVID-19 illness? Frontiers in Pharmacology, 11, 579944.Sheth, B.; Paruta A.N.; Niger, R. (1966), Solubility of acetanilide and several derivatives in sucrose solution, Journal of Pharmaceutical Sciences, 55, 1144-1147.Soltanpour, S.; Jouyban, A. (2010), Solubility of acetaminophen and ibuprofen in binary and ternary mixtures of polyethylene glycol 600, ethanol and water, Chemical and Pharmaceutical Bulletin (Tokyo), 58, 219–224.Sweetman, S.C. (editor) (2009), Martindale: The Complete Drug Reference, 36th ed., Pharmaceutical Press, London.Tinjacá, D.A.; Muñoz, M.M.; Jouyban, A.; Martínez, F.; Acree, W.E., Jr. (2019), Equilibrium solubility, preferential solvation and apparent specific volume of sucrose in some {cosolvent (1) + water (2)} mixtures at 298.2 K, Physics and Chemistry of Liquids, 57, 259–273.Tinjacá, D.A.; Muñoz, M.M.; Rahimpour, E.; Jouyban, A.; Martínez, F.; Acree, W.E., Jr. (2018), Solubility and apparent specific volume of sucrose in some aqueous polyethylene glycol mixtures at 298.2 K, Pharmaceutical Sciences (Tabriz), 24, 163–167.Trissel, L.A. (editor) (2013), Handbook on Injectable Drugs, 17th ed., American Society of Health-System Pharmacists, Bethesda (MD).Tsapatsaris, N.; Kolesov, B.A.; Fischer, J.; Boldyreva, E.V.; Daemen, L.; Eckert, J.; Bordallo, H.N. (2014), Polymorphism of paracetamol: A new understanding of molecular flexibility through local methyl dynamics, Molecular Pharmaceutics, 11, 1032–1041.Yalkowsky, S.H. (1999), Solubility and Solubilization in Aqueous Media, American Chemical Society and Oxford University Press, New York (NY), pp. 91–134.Yoshioka, S.; Stella, V.J. (2002), Stability of Drugs and Dosage Forms, Kluwer Academic Publishers, New York (NY).Yurquina, A.; Manzur, M.E.; Brito, P.; Manzo, R.; Molina, M.A.A. (2007), Physicochemical studies of acetaminophen in water-PEG 400 systems, Journal of Molecular Liquids, 133, 47–53.Zadali-Asghar, S.; Jouyban, A.; Martinez, F.; Rahimpour, E. (2018), Solubility of naproxen in ternary mixtures of {ethanol + propylene glycol + water} at various temperatures: Data correlation and thermodynamic analysis, Journal of Molecular Liquids, 268, 517–522.EstudiantesInvestigadoresMaestrosLICENSElicense.txtlicense.txttext/plain; charset=utf-85879https://repositorio.unal.edu.co/bitstream/unal/82880/1/license.txteb34b1cf90b7e1103fc9dfd26be24b4aMD51ORIGINAL461291.2022.pdf461291.2022.pdfTesis de Maestría en Ciencias Farmacéuticasapplication/pdf2641012https://repositorio.unal.edu.co/bitstream/unal/82880/2/461291.2022.pdf8a3129a78076eb40f2bf4a4495eb7142MD52THUMBNAIL461291.2022.pdf.jpg461291.2022.pdf.jpgGenerated Thumbnailimage/jpeg4746https://repositorio.unal.edu.co/bitstream/unal/82880/3/461291.2022.pdf.jpgfe9355f1c3c32360d2168441dfed7f4cMD53unal/82880oai:repositorio.unal.edu.co:unal/828802023-08-12 23:03:49.173Repositorio Institucional Universidad Nacional de Colombiarepositorio_nal@unal.edu.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

Publicaciones similares