Polymorphic and quantum chemistry characterization of candesartan cilexetil: importance for the correct drug classification according to biopharmaceutics classification system

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dc.creatorDébora Priscila de Campos
dc.creatorNeila Márcia Silva Barcellos
dc.creatorRenata Rodrigues Lima
dc.creatorRanylson Marcello Leal Savedra
dc.creatorMelissa Fabíola Siqueira
dc.creatorMaria Irene Yoshida
dc.creatorWagner da Nova Mussel
dc.creatorJacqueline de Souza
dc.date.accessioned2023-03-03T17:59:36Z
dc.date.accessioned2025-09-09T00:30:53Z
dc.date.available2023-03-03T17:59:36Z
dc.date.issued2018-10
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.description.sponsorshipOutra Agência
dc.identifier.doihttps://doi.org/10.1208/s12249-018-1129-6
dc.identifier.issn1530-9932
dc.identifier.urihttps://hdl.handle.net/1843/50646
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.rightsAcesso Restrito
dc.subjectQuímica quântica
dc.subjectFísico-química
dc.subjectPolimorfismo (Cristalografia)
dc.subjectSolubilidade
dc.subjectPermeabilidade
dc.subjectMedicamentos - Estabilidade
dc.subjectAgentes hipotensores
dc.subjectBiofarmacêutica
dc.subjectFármacos - Classificação
dc.subjectSolvação
dc.subjectOrbitais moleculares
dc.subjectAnálise térmica
dc.subjectRaios X - Difração
dc.subject.otherPolymorphism
dc.subject.otherQuantum chemistry
dc.subject.otherBiopharmaceutics classification cystem
dc.subject.otherEquilibrium solubility
dc.subject.otherCandesartan cilexetil
dc.titlePolymorphic and quantum chemistry characterization of candesartan cilexetil: importance for the correct drug classification according to biopharmaceutics classification system
dc.typeArtigo de periódico
local.citation.epage3028
local.citation.issue7
local.citation.spage3019
local.citation.volume19
local.description.resumoThe recommended method for the biopharmaceutical evaluation of drug solubility is the shake flask; however, there are discrepancies reported about the solubility of certain compounds measured with this method, one of them is candesartan cilexetil. The present work aimed to elucidate the solubility of candesartan cilexetil by associating others assays such as stability determination, polymorphic characterization and in silico calculations of intrinsic solubility, ionized species, and electronic structures using quantum chemistry descriptors (frontier molecular orbitals and Fukui functions). For the complete biopharmaceutical classification, we also reviewed the permeability data available. The polymorphic form used was previously identified as the form I of candesartan cilexetil. The solubility was evaluated in biorelevant media in the pH range of 1.2–6.8 at 37.0°C according to the stability previously assessed. The solubility of candesartan cilexetil is pH dependent and the dose/solubility ratios obtained demonstrated the low solubility of the prodrug. The in silico calculations supported the found results and evidenced the main groups involved in the solvation, benzimidazole, and tetrazol-biphenyl. The human absolute bioavailability reported demonstrates that candesartan cilexetil has low permeability and when associated with the low solubility allows to classify it as class 4 of the Biopharmaceutics Classification System.
local.identifier.orcidhttps://orcid.org/0000-0003-3619-5965
local.identifier.orcidhttps://orcid.org/0000-0003-0013-9937
local.identifier.orcidhttps://orcid.org/0000-0002-4809-577X
local.identifier.orcidhttps://orcid.org/0000-0002-0277-0418
local.identifier.orcidhttps://orcid.org/0000-0002-6795-9457
local.identifier.orcidhttps://orcid.org/0000-0002-9768-9830
local.identifier.orcidhttps://orcid.org/0000-0003-0869-023X
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://link.springer.com/article/10.1208/s12249-018-1129-6

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