High-pressure studies of pharmaceuticals: An exploration of the behavior of piracetam

Francesca P A Fabbiani; David R. Allan; William I F David; Alistair J. Davidson; Alistair R. Lennie; Simon Parsons; Colin R. Pulham; John E. Warren

doi:10.1021/cg0607710

High-pressure studies of pharmaceuticals: An exploration of the behavior of piracetam

Francesca P A Fabbiani, David R. Allan, William I F David, Alistair J. Davidson, Alistair R. Lennie, Simon Parsons, Colin R. Pulham, John E. Warren

Research output: Contribution to journal › Article › peer-review

Abstract

The structural response of the nootropic drug piracetam (2-oxo-pyrrolidineacetamide) to both direct compression and high-pressure recrystallization from aqueous solution is reported. Crystals obtained by these methods have been characterized in situ by single-crystal X-ray diffraction. Compression of form II between pressures of 0.45-0.70 GPa caused a reversible, single-crystal to single-crystal transition to give a new polymorph, form V. Crystallization from a dilute aqueous solution of piracetam at a pressure of 0.6 GPa via crystallization of high-pressure ice-VI resulted in the formation of a previously unreported dihydrate. The molecular packing arrangements of these new structures are compared with the known polymorphs and hydrates of piracetam. This study highlights how the systematic variation of pressure is a powerful method for the exploration of polymorphism and solvate formation and has the potential to add a further dimension to polymorph screening of pharmaceuticals. © 2007 American Chemical Society.

Original language	English
Pages (from-to)	1115-1124
Number of pages	9
Journal	Crystal Growth and Design
Volume	7
Issue number	6
DOIs	https://doi.org/10.1021/cg0607710
Publication status	Published - Jun 2007

Keywords

CRYSTAL-STRUCTURE
{CRYSTAL-STRUCTURE
HYDROGEN-BOND
{HYDROGEN-BOND
HYDROSTATIC-PRESSURE
{HYDROSTATIC-PRESSURE
INDUCED
INDUCED} {PHASE-TRANSITION
MOLECULAR-CRYSTALS
{MOLECULAR-CRYSTALS
SOLID-STATE
ORGANIC-CRYSTALS
{ORGANIC-CRYSTALS
SINGLE-CRYSTAL
SODIUM OXALATE
OXALATE
{PHASE-TRANSITION
{SINGLE-CRYSTAL
SODIUM
SODIUM} {OXALATE
{SOLID-STATE
X-RAY-DIFFRACTION
INDUCED PHASE-TRANSITION

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10.1021/cg0607710

CCDC 621827: Experimental Crystal Structure Determination
Fabbiani, F. P. A. (Contributor), Allan, D. R. (Contributor), David, W. I. F. (Contributor), Davidson, A. J. (Contributor), Lennie, A. R. (Contributor), Parsons, S. (Contributor), Pulham, C. R. (Contributor) & Warren, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2007
DOI: 10.5517/ccnw1yh, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccnw1yh&sid=DataCite
Dataset
CCDC 621826: Experimental Crystal Structure Determination
Fabbiani, F. P. A. (Contributor), Allan, D. R. (Contributor), David, W. I. F. (Contributor), Davidson, A. J. (Contributor), Lennie, A. R. (Contributor), Parsons, S. (Contributor), Pulham, C. R. (Contributor) & Warren, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2007
DOI: 10.5517/ccnw1xg, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccnw1xg&sid=DataCite
Dataset
CCDC 621824: Experimental Crystal Structure Determination
Fabbiani, F. P. A. (Contributor), Allan, D. R. (Contributor), David, W. I. F. (Contributor), Davidson, A. J. (Contributor), Lennie, A. R. (Contributor), Parsons, S. (Contributor), Pulham, C. R. (Contributor) & Warren, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2007
DOI: 10.5517/ccnw1vd, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccnw1vd&sid=DataCite
Dataset

Cite this

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title = "High-pressure studies of pharmaceuticals: An exploration of the behavior of piracetam",

abstract = "The structural response of the nootropic drug piracetam (2-oxo-pyrrolidineacetamide) to both direct compression and high-pressure recrystallization from aqueous solution is reported. Crystals obtained by these methods have been characterized in situ by single-crystal X-ray diffraction. Compression of form II between pressures of 0.45-0.70 GPa caused a reversible, single-crystal to single-crystal transition to give a new polymorph, form V. Crystallization from a dilute aqueous solution of piracetam at a pressure of 0.6 GPa via crystallization of high-pressure ice-VI resulted in the formation of a previously unreported dihydrate. The molecular packing arrangements of these new structures are compared with the known polymorphs and hydrates of piracetam. This study highlights how the systematic variation of pressure is a powerful method for the exploration of polymorphism and solvate formation and has the potential to add a further dimension to polymorph screening of pharmaceuticals. {\textcopyright} 2007 American Chemical Society.",

keywords = "CRYSTAL-STRUCTURE, {CRYSTAL-STRUCTURE, HYDROGEN-BOND, {HYDROGEN-BOND, HYDROSTATIC-PRESSURE, {HYDROSTATIC-PRESSURE, INDUCED, INDUCED} {PHASE-TRANSITION, MOLECULAR-CRYSTALS, {MOLECULAR-CRYSTALS, SOLID-STATE, ORGANIC-CRYSTALS, {ORGANIC-CRYSTALS, SINGLE-CRYSTAL, SODIUM OXALATE, OXALATE, {PHASE-TRANSITION, {SINGLE-CRYSTAL, SODIUM, SODIUM} {OXALATE, {SOLID-STATE, X-RAY-DIFFRACTION, INDUCED PHASE-TRANSITION",

author = "Fabbiani, {Francesca P A} and Allan, {David R.} and David, {William I F} and Davidson, {Alistair J.} and Lennie, {Alistair R.} and Simon Parsons and Pulham, {Colin R.} and Warren, {John E.}",

note = "6",

year = "2007",

month = jun,

doi = "10.1021/cg0607710",

language = "English",

volume = "7",

pages = "1115--1124",

journal = "Crystal Growth and Design",

issn = "1528-7483",

publisher = "American Chemical Society",

number = "6",

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AU - Fabbiani, Francesca P A

AU - Allan, David R.

AU - David, William I F

AU - Davidson, Alistair J.

AU - Lennie, Alistair R.

AU - Parsons, Simon

AU - Pulham, Colin R.

AU - Warren, John E.

N1 - 6

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N2 - The structural response of the nootropic drug piracetam (2-oxo-pyrrolidineacetamide) to both direct compression and high-pressure recrystallization from aqueous solution is reported. Crystals obtained by these methods have been characterized in situ by single-crystal X-ray diffraction. Compression of form II between pressures of 0.45-0.70 GPa caused a reversible, single-crystal to single-crystal transition to give a new polymorph, form V. Crystallization from a dilute aqueous solution of piracetam at a pressure of 0.6 GPa via crystallization of high-pressure ice-VI resulted in the formation of a previously unreported dihydrate. The molecular packing arrangements of these new structures are compared with the known polymorphs and hydrates of piracetam. This study highlights how the systematic variation of pressure is a powerful method for the exploration of polymorphism and solvate formation and has the potential to add a further dimension to polymorph screening of pharmaceuticals. © 2007 American Chemical Society.

AB - The structural response of the nootropic drug piracetam (2-oxo-pyrrolidineacetamide) to both direct compression and high-pressure recrystallization from aqueous solution is reported. Crystals obtained by these methods have been characterized in situ by single-crystal X-ray diffraction. Compression of form II between pressures of 0.45-0.70 GPa caused a reversible, single-crystal to single-crystal transition to give a new polymorph, form V. Crystallization from a dilute aqueous solution of piracetam at a pressure of 0.6 GPa via crystallization of high-pressure ice-VI resulted in the formation of a previously unreported dihydrate. The molecular packing arrangements of these new structures are compared with the known polymorphs and hydrates of piracetam. This study highlights how the systematic variation of pressure is a powerful method for the exploration of polymorphism and solvate formation and has the potential to add a further dimension to polymorph screening of pharmaceuticals. © 2007 American Chemical Society.

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U2 - 10.1021/cg0607710

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SN - 1528-7483

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EP - 1124

JO - Crystal Growth and Design

JF - Crystal Growth and Design

IS - 6

ER -

High-pressure studies of pharmaceuticals: An exploration of the behavior of piracetam

Abstract

Keywords

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Datasets

CCDC 621827: Experimental Crystal Structure Determination

CCDC 621826: Experimental Crystal Structure Determination

CCDC 621824: Experimental Crystal Structure Determination

Cite this