Racemic salts and solid solutions of enantiomers of the antihypertensive drug carvedilol

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dc.creatorLuan Farinelli Diniz
dc.creatorPaulo de Sousa Carvalho Júnior
dc.creatorWagner da Nova Mussel
dc.creatorMaria Irene Yoshida
dc.creatorRenata Diniz
dc.creatorChristian Fernandes
dc.date.accessioned2023-03-03T17:42:53Z
dc.date.accessioned2025-09-09T00:42:12Z
dc.date.available2023-03-03T17:42:53Z
dc.date.issued2019-08
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.identifier.doihttps://doi.org/10.1021/acs.cgd.9b00263
dc.identifier.issn1528-7505
dc.identifier.urihttps://hdl.handle.net/1843/50644
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.rightsAcesso Restrito
dc.subjectQuímica analítica
dc.subjectÁcido tartárico
dc.subjectÁcido oxálico
dc.subjectEnantiômeros
dc.subjectAgentes hipotensores
dc.subjectCristalografia
dc.subjectAnálise conformacional
dc.subjectRaios X - Difração
dc.subjectFourier, Espectroscopia de infravermelho por transformada de
dc.subjectMicroscopia
dc.subjectTermogravimetria
dc.subjectCalorimetria
dc.subjectDeposição química de vapor
dc.subjectEstrutura molecular
dc.subjectCristais
dc.subjectFarmacologia
dc.subjectMedicamentos - Análise
dc.subject.otherCarvedilol
dc.subject.otherSolid solutions
dc.subject.otherEnantiomers
dc.subject.otherX-ray diffraction
dc.subject.otherCrystal structure
dc.subject.otherChemical vapor deposition
dc.subject.otherCrystals
dc.subject.otherMolecular structure
dc.subject.otherSalts
dc.titleRacemic salts and solid solutions of enantiomers of the antihypertensive drug carvedilol
dc.typeArtigo de periódico
local.citation.epage4509
local.citation.issue8
local.citation.spage4498
local.citation.volume19
local.description.resumoThe R and S enantiomers of the antihypertensive drug carvedilol (CVD) can display remarkable miscibility in the crystalline state allowing this active pharmaceutical ingredient (API) to form a solid-solution of enantiomers (SSEs) as well as racemic compounds. Although rare and still little explored, these intriguing systems can also be used to design racemic multicomponent crystal forms toward the improvement of undesirable pharmaceutical properties of APIs. In this study, aiming to understand why there is miscibility between the enantiomers during the supramolecular recognition and crystallization processes of the CVD in the presence of salt formers, two SSEs and one racemic salt were prepared from the reaction of CVD with pharmaceutically acceptable HCl, HBr, and oxalic acids. Two monohydrated isostructural salts, hydrochloride (CVD-HCl-H2O) and hydrobromide (CVD-HBr-H2O), crystallize as racemic SSEs. These unique systems are formed from the miscibility of the R···R and S···S homochiral units that propagate into enantiomerically enriched one-dimensional chains through H-bonds with water molecules along the crystal. The oxalate salt (CVD-OXA), in turn, crystallizes as a standard racemic compound since the oxalate anions, which lie in the inversion center, are directly H-bonded to both R and S CVD enantiomers, forming racemic ionic units that extend along the structure. Complementary to the crystallographic study, conformational and Hirshfeld surface analysis were also performed based on the single-crystal X-ray diffraction data. The salt formations were confirmed from the Fourier transform infrared spectroscopy as well as powder X-ray diffraction patterns, and their thermal behaviors were investigated by a combination of differential scanning calorimetry, thermogravimetric, and hot-stage microscopy techniques.
local.identifier.orcidhttps://orcid.org/0000-0003-4702-9065
local.identifier.orcidhttps://orcid.org/0000-0002-5551-9155
local.identifier.orcidhttps://orcid.org/0000-0002-9768-9830
local.identifier.orcidhttps://orcid.org/0000-0002-6795-9457
local.identifier.orcidhttps://orcid.org/0000-0001-9042-9094
local.identifier.orcidhttps://orcid.org/0000-0002-3905-3674
local.publisher.countryBrasil
local.publisher.departmentFAR - DEPARTAMENTO DE PRODUTOS FARMACÊUTICOS
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://pubs.acs.org/doi/10.1021/acs.cgd.9b00263

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