Pharmaceutical solids and exploring chiral resolution using cocrystallization

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dc.contributor.advisor Lawrence, Simon E. en
dc.contributor.advisor Maguire, Anita R. en Khandavilli, Udaya Bhaskara Rao 2018-02-16T11:33:39Z 2017 2017
dc.identifier.citation Khandavilli, U. B. 2017. Pharmaceutical solids and exploring chiral resolution using cocrystallization. PhD Thesis, University College Cork. en
dc.description.abstract This thesis is concerned with the solid-state and physicochemical properties of multi-component forms of model systems and active pharmaceutical ingredients, with particular emphasis on cocrystallization; a method that allow formation of multi-component forms for compounds with non-ionizable or weakly ionisable functional groups. The research has been divided into four chapters. Chapter One discusses and illustrates the literature for the solid-state of organic compounds; topics covered include polymorphism, hydrates, solvates, cocrystallization and salt formation, Chapter Two describes the synthesis and cocrystallization of model drugs with non-ionisable functional groups. Two series of phenylcarboximides with different alkyl group substitution (varying from methyl to tert-butyl) on a chiral centre either α or β to the amide functional group have been synthesised and their solid-state properties examined. Cocrystallization studies reveal that the drug salicylic acid is a reliable coformer with all the amides examined. The polymorphic behaviour of the cocrystals has been fully explored. Chapter Three examines cocrystallization and salt formation as ways to improve the poor solubility associated with nutraceutical compounds, by investigating two model nutraceuticals: sinapic acid and naringenin. Their solid-state forms, solubility and dissolution properties were determined. Chapter Four describes multi-component forms of actual drugs, namely sulpiride and probenecid. Inorganic and organic salts of sulpiride were synthesized and structural and physicochemical properties. Transfer of mechanical flexibility from the drug to its multi-component form has been demonstrated for a GRAS coformer. The design of ternary cocrystals using compounds with phenolic and carboxylic acid functional groups was envisaged and achieved. en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher University College Cork en
dc.rights © 2017, Udaya Bhaskararao Khandavilli . en
dc.rights.uri en
dc.subject Polymorph en
dc.subject Co-crystal en
dc.subject Pharmaceutical salt en
dc.subject Conglomerate en
dc.subject Nutraceuticals en
dc.subject Kryptoracemic en
dc.subject Co-crystal polymorph en
dc.subject Salt co-crystal en
dc.subject Ternary co-crystal en
dc.subject Bending crystals en
dc.title Pharmaceutical solids and exploring chiral resolution using cocrystallization en
dc.type Doctoral thesis en
dc.type.qualificationlevel Doctoral Degree (Structured) en
dc.type.qualificationname PhD (Science) en
dc.internal.availability Full text not available en Indefinite en 10000-01-01
dc.description.version Accepted Version
dc.contributor.funder Science Foundation Ireland en
dc.description.status Not peer reviewed en Chemistry en
dc.check.reason This thesis is due for publication or the author is actively seeking to publish this material en
dc.check.opt-out Yes en
dc.thesis.opt-out true
dc.check.entireThesis Entire Thesis Restricted
dc.check.embargoformat Both hard copy thesis and e-thesis en
dc.internal.conferring Spring 2018 en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/ en

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© 2017, Udaya Bhaskararao Khandavilli . Except where otherwise noted, this item's license is described as © 2017, Udaya Bhaskararao Khandavilli .
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