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Mechanochemical Synthesis and Physicochemical Characterization of Previously Unreported Praziquantel Solvates with 2-Pyrrolidone and Acetic Acid.

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cam.issuedOnline2021-10-02
dc.contributor.authorZanolla, Debora
dc.contributor.authorGigli, Lara
dc.contributor.authorHasa, Dritan
dc.contributor.authorChierotti, Michele R
dc.contributor.authorArhangelskis, Mihails
dc.contributor.authorDemitri, Nicola
dc.contributor.authorJones, William
dc.contributor.authorVoinovich, Dario
dc.contributor.authorPerissutti, Beatrice
dc.contributor.orcidZanolla, Debora [0000-0001-7549-7806]
dc.contributor.orcidGigli, Lara [0000-0002-7787-5804]
dc.contributor.orcidChierotti, Michele R [0000-0002-8734-6009]
dc.contributor.orcidArhangelskis, Mihails [0000-0003-1150-3108]
dc.contributor.orcidDemitri, Nicola [0000-0003-0288-3233]
dc.contributor.orcidVoinovich, Dario [0000-0003-3830-8038]
dc.contributor.orcidPerissutti, Beatrice [0000-0002-5766-4014]
dc.date.accessioned2022-01-06T11:51:14Z
dc.date.available2022-01-06T11:51:14Z
dc.date.issued2021-10-02
dc.date.updated2022-01-06T11:51:13Z
dc.description.abstractTwo new solvates of the widely used anthelminthic Praziquantel (PZQ) were obtained through mechanochemical screening with different liquid additives. Specifically, 2-pyrrolidone and acetic acid gave solvates with 1:1 stoichiometry (PZQ-AA and PZQ-2P, respectively). A wide-ranging characterization of the new solid forms was carried out by means of powder X-ray diffraction, differential scanning calorimetry, FT-IR, solid-state NMR and biopharmaceutical analyses (solubility and intrinsic dissolution studies). Besides, the crystal structures of the two new solvates were solved from their Synchrotron-PXRD pattern: the solvates are isostructural, with equivalent triclinic packing. In both structures acetic acid and 2-pyrrolidone showed a strong interaction with the PZQ molecule via hydrogen bond. Even though previous studies have shown that PZQ is conformationally flexible, the same syn conformation as the PZQ Form A of the C=O groups of the piperazinone-cyclohexylcarbonyl segment is involved in these two new solid forms. In terms of biopharmaceutical properties, PZQ-AA and PZQ-2P exhibited water solubility and intrinsic dissolution rate much greater than those of anhydrous Form A.
dc.identifier.doi10.17863/CAM.79611
dc.identifier.eissn1999-4923
dc.identifier.issn1999-4923
dc.identifier.otherPMC8540171
dc.identifier.other34683899
dc.identifier.urihttps://www.repository.cam.ac.uk/handle/1810/332165
dc.languageeng
dc.language.isoeng
dc.publisherMDPI AG
dc.publisher.urlhttp://dx.doi.org/10.3390/pharmaceutics13101606
dc.rightsAttribution 4.0 International
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.sourceessn: 1999-4923
dc.sourcenlmid: 101534003
dc.subject2-pyrrolidone
dc.subjectacetic acid
dc.subjectliquid-assisted grinding
dc.subjectmechanochemistry
dc.subjectpraziquantel
dc.subjectsolvates
dc.titleMechanochemical Synthesis and Physicochemical Characterization of Previously Unreported Praziquantel Solvates with 2-Pyrrolidone and Acetic Acid.
dc.typeArticle
dcterms.dateAccepted2021-09-28
prism.issueIdentifier10
prism.publicationNamePharmaceutics
prism.volume13
pubs.funder-project-idNational Science Center Poland (2018/31/D/ST5/03619)
rioxxterms.licenseref.urihttps://creativecommons.org/licenses/by/4.0/
rioxxterms.versionVoR
rioxxterms.versionofrecord10.3390/pharmaceutics13101606

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