New Lidocaine-Based Pharmaceutical Cocrystals: Preparation, Characterization, and Influence of the Racemic vs. Enantiopure Coformer on the Physico-Chemical Properties

Panpan Ma; Balthazar Toussaint; Enrica Angela Roberti; Noémie Scornet; Axel Santos Silva; Luis Castillo Henríquez; Monique Cadasse; Philippe Négrier; Stéphane Massip; Hanh Dufat; Karim Hammad; Cecilia Baraldi; Maria Cristina Gamberini; Cyrille Richard; Stéphane Veesler; Philippe Espeau; Tu Lee; Yohann Corvis

doi:10.3390/pharmaceutics15041102

New Lidocaine-Based Pharmaceutical Cocrystals: Preparation, Characterization, and Influence of the Racemic vs. Enantiopure Coformer on the Physico-Chemical Properties

Panpan Ma, Balthazar Toussaint, Enrica Angela Roberti, Noémie Scornet, Axel Santos Silva, Luis Castillo Henríquez, Monique Cadasse, Philippe Négrier, Stéphane Massip, Hanh Dufat, Karim Hammad, Cecilia Baraldi, Maria Cristina Gamberini, Cyrille Richard, Stéphane Veesler, Philippe Espeau, Tu Lee, Yohann Corvis

Department of Chemical and Materials Engineering

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

3 Scopus citations

Abstract

This study describes the preparation, characterization, and influence of the enantiopure vs. racemic coformer on the physico-chemical properties of a pharmaceutical cocrystal. For that purpose, two new 1:1 cocrystals, namely lidocaine:dl-menthol and lidocaine:d-menthol, were prepared. The menthol racemate-based cocrystal was evaluated by means of X-ray diffraction, infrared spectroscopy, Raman, thermal analysis, and solubility experiments. The results were exhaustively compared with the first menthol-based pharmaceutical cocrystal, i.e., lidocaine:l-menthol, discovered in our group 12 years ago. Furthermore, the stable lidocaine/dl-menthol phase diagram has been screened, thoroughly evaluated, and compared to the enantiopure phase diagram. Thus, it has been proven that the racemic vs. enantiopure coformer leads to increased solubility and improved dissolution of lidocaine due to the low stable form induced by menthol molecular disorder in the lidocaine:dl-menthol cocrystal. To date, the 1:1 lidocaine:dl-menthol cocrystal is the third menthol-based pharmaceutical cocrystal, after the 1:1 lidocaine:l-menthol and the 1:2 lopinavir:l-menthol cocrystals reported in 2010 and 2022, respectively. Overall, this study shows promising potential for designing new materials with both improved characteristics and functional properties in the fields of pharmaceutical sciences and crystal engineering.

Original language	English
Article number	1102
Journal	Pharmaceutics
Volume	15
Issue number	4
DOIs	https://doi.org/10.3390/pharmaceutics15041102
State	Published - Apr 2023

Keywords

cocrystallization
crystal engineering
dissolution kinetics
dl-menthol
lidocaine
physico-chemical compatibility
solid state
solubility enhancement
thermodynamic stability

Access to Document

10.3390/pharmaceutics15041102

CCDC 2232113: Experimental Crystal Structure Determination
Ma, P. (Contributor), Toussaint, B. (Contributor), Roberti, E. A. (Contributor), Scornet, N. (Contributor), Santos Silva, A. (Contributor), Castillo Henríquez, L. (Contributor), Cadasse, M. (Contributor), Négrier, P. (Contributor), Massip, S. (Contributor), Dufat, H. (Contributor), Hammad, K. (Contributor), Baraldi, C. (Contributor), Gamberini, M. C. (Contributor), Richard, C. (Contributor), Veesler, S. (Contributor), Espeau, P. (Contributor), Lee, T. (Contributor) & Corvis, Y. (Contributor), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc2dxpnp, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2dxpnp&sid=DataCite
Dataset
CCDC 2248363: Experimental Crystal Structure Determination
Ma, P. (Contributor), Toussaint, B. (Contributor), Roberti, E. A. (Contributor), Scornet, N. (Contributor), Santos Silva, A. (Contributor), Castillo Henríquez, L. (Contributor), Cadasse, M. (Contributor), Négrier, P. (Contributor), Massip, S. (Contributor), Dufat, H. (Contributor), Hammad, K. (Contributor), Baraldi, C. (Contributor), Gamberini, M. C. (Contributor), Richard, C. (Contributor), Veesler, S. (Contributor), Espeau, P. (Contributor), Lee, T. (Contributor) & Corvis, Y. (Contributor), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc2fglvc, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2fglvc&sid=DataCite
Dataset
CCDC 2231851: Experimental Crystal Structure Determination
Ma, P. (Contributor), Toussaint, B. (Contributor), Roberti, E. A. (Contributor), Scornet, N. (Contributor), Santos Silva, A. (Contributor), Castillo Henríquez, L. (Contributor), Cadasse, M. (Contributor), Négrier, P. (Contributor), Massip, S. (Contributor), Dufat, H. (Contributor), Hammad, K. (Contributor), Baraldi, C. (Contributor), Gamberini, M. C. (Contributor), Richard, C. (Contributor), Veesler, S. (Contributor), Espeau, P. (Contributor), Lee, T. (Contributor) & Corvis, Y. (Contributor), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc2dxf6z, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2dxf6z&sid=DataCite
Dataset

Cite this

Ma, P., Toussaint, B., Roberti, E. A., Scornet, N., Santos Silva, A., Castillo Henríquez, L., Cadasse, M., Négrier, P., Massip, S., Dufat, H., Hammad, K., Baraldi, C., Gamberini, M. C., Richard, C., Veesler, S., Espeau, P., Lee, T., & Corvis, Y. (2023). New Lidocaine-Based Pharmaceutical Cocrystals: Preparation, Characterization, and Influence of the Racemic vs. Enantiopure Coformer on the Physico-Chemical Properties. Pharmaceutics, 15(4), Article 1102. https://doi.org/10.3390/pharmaceutics15041102

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title = "New Lidocaine-Based Pharmaceutical Cocrystals: Preparation, Characterization, and Influence of the Racemic vs. Enantiopure Coformer on the Physico-Chemical Properties",

abstract = "This study describes the preparation, characterization, and influence of the enantiopure vs. racemic coformer on the physico-chemical properties of a pharmaceutical cocrystal. For that purpose, two new 1:1 cocrystals, namely lidocaine:dl-menthol and lidocaine:d-menthol, were prepared. The menthol racemate-based cocrystal was evaluated by means of X-ray diffraction, infrared spectroscopy, Raman, thermal analysis, and solubility experiments. The results were exhaustively compared with the first menthol-based pharmaceutical cocrystal, i.e., lidocaine:l-menthol, discovered in our group 12 years ago. Furthermore, the stable lidocaine/dl-menthol phase diagram has been screened, thoroughly evaluated, and compared to the enantiopure phase diagram. Thus, it has been proven that the racemic vs. enantiopure coformer leads to increased solubility and improved dissolution of lidocaine due to the low stable form induced by menthol molecular disorder in the lidocaine:dl-menthol cocrystal. To date, the 1:1 lidocaine:dl-menthol cocrystal is the third menthol-based pharmaceutical cocrystal, after the 1:1 lidocaine:l-menthol and the 1:2 lopinavir:l-menthol cocrystals reported in 2010 and 2022, respectively. Overall, this study shows promising potential for designing new materials with both improved characteristics and functional properties in the fields of pharmaceutical sciences and crystal engineering.",

keywords = "cocrystallization, crystal engineering, dissolution kinetics, dl-menthol, lidocaine, physico-chemical compatibility, solid state, solubility enhancement, thermodynamic stability",

author = "Panpan Ma and Balthazar Toussaint and Roberti, {Enrica Angela} and No{\'e}mie Scornet and {Santos Silva}, Axel and {Castillo Henr{\'i}quez}, Luis and Monique Cadasse and Philippe N{\'e}grier and St{\'e}phane Massip and Hanh Dufat and Karim Hammad and Cecilia Baraldi and Gamberini, {Maria Cristina} and Cyrille Richard and St{\'e}phane Veesler and Philippe Espeau and Tu Lee and Yohann Corvis",

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Ma, P, Toussaint, B, Roberti, EA, Scornet, N, Santos Silva, A, Castillo Henríquez, L, Cadasse, M, Négrier, P, Massip, S, Dufat, H, Hammad, K, Baraldi, C, Gamberini, MC, Richard, C, Veesler, S, Espeau, P, Lee, T & Corvis, Y 2023, 'New Lidocaine-Based Pharmaceutical Cocrystals: Preparation, Characterization, and Influence of the Racemic vs. Enantiopure Coformer on the Physico-Chemical Properties', Pharmaceutics, vol. 15, no. 4, 1102. https://doi.org/10.3390/pharmaceutics15041102

TY - JOUR

T1 - New Lidocaine-Based Pharmaceutical Cocrystals

T2 - Preparation, Characterization, and Influence of the Racemic vs. Enantiopure Coformer on the Physico-Chemical Properties

AU - Ma, Panpan

AU - Toussaint, Balthazar

AU - Roberti, Enrica Angela

AU - Scornet, Noémie

AU - Santos Silva, Axel

AU - Castillo Henríquez, Luis

AU - Cadasse, Monique

AU - Négrier, Philippe

AU - Massip, Stéphane

AU - Dufat, Hanh

AU - Hammad, Karim

AU - Baraldi, Cecilia

AU - Gamberini, Maria Cristina

AU - Richard, Cyrille

AU - Veesler, Stéphane

AU - Espeau, Philippe

AU - Lee, Tu

AU - Corvis, Yohann

PY - 2023/4

Y1 - 2023/4

N2 - This study describes the preparation, characterization, and influence of the enantiopure vs. racemic coformer on the physico-chemical properties of a pharmaceutical cocrystal. For that purpose, two new 1:1 cocrystals, namely lidocaine:dl-menthol and lidocaine:d-menthol, were prepared. The menthol racemate-based cocrystal was evaluated by means of X-ray diffraction, infrared spectroscopy, Raman, thermal analysis, and solubility experiments. The results were exhaustively compared with the first menthol-based pharmaceutical cocrystal, i.e., lidocaine:l-menthol, discovered in our group 12 years ago. Furthermore, the stable lidocaine/dl-menthol phase diagram has been screened, thoroughly evaluated, and compared to the enantiopure phase diagram. Thus, it has been proven that the racemic vs. enantiopure coformer leads to increased solubility and improved dissolution of lidocaine due to the low stable form induced by menthol molecular disorder in the lidocaine:dl-menthol cocrystal. To date, the 1:1 lidocaine:dl-menthol cocrystal is the third menthol-based pharmaceutical cocrystal, after the 1:1 lidocaine:l-menthol and the 1:2 lopinavir:l-menthol cocrystals reported in 2010 and 2022, respectively. Overall, this study shows promising potential for designing new materials with both improved characteristics and functional properties in the fields of pharmaceutical sciences and crystal engineering.

AB - This study describes the preparation, characterization, and influence of the enantiopure vs. racemic coformer on the physico-chemical properties of a pharmaceutical cocrystal. For that purpose, two new 1:1 cocrystals, namely lidocaine:dl-menthol and lidocaine:d-menthol, were prepared. The menthol racemate-based cocrystal was evaluated by means of X-ray diffraction, infrared spectroscopy, Raman, thermal analysis, and solubility experiments. The results were exhaustively compared with the first menthol-based pharmaceutical cocrystal, i.e., lidocaine:l-menthol, discovered in our group 12 years ago. Furthermore, the stable lidocaine/dl-menthol phase diagram has been screened, thoroughly evaluated, and compared to the enantiopure phase diagram. Thus, it has been proven that the racemic vs. enantiopure coformer leads to increased solubility and improved dissolution of lidocaine due to the low stable form induced by menthol molecular disorder in the lidocaine:dl-menthol cocrystal. To date, the 1:1 lidocaine:dl-menthol cocrystal is the third menthol-based pharmaceutical cocrystal, after the 1:1 lidocaine:l-menthol and the 1:2 lopinavir:l-menthol cocrystals reported in 2010 and 2022, respectively. Overall, this study shows promising potential for designing new materials with both improved characteristics and functional properties in the fields of pharmaceutical sciences and crystal engineering.

KW - cocrystallization

KW - crystal engineering

KW - dissolution kinetics

KW - dl-menthol

KW - lidocaine

KW - physico-chemical compatibility

KW - solid state

KW - solubility enhancement

KW - thermodynamic stability

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U2 - 10.3390/pharmaceutics15041102

DO - 10.3390/pharmaceutics15041102

M3 - 期刊論文

AN - SCOPUS:85154554567

SN - 1999-4923

VL - 15

JO - Pharmaceutics

JF - Pharmaceutics

IS - 4

M1 - 1102

ER -

New Lidocaine-Based Pharmaceutical Cocrystals: Preparation, Characterization, and Influence of the Racemic vs. Enantiopure Coformer on the Physico-Chemical Properties

Abstract

Keywords

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Datasets

CCDC 2232113: Experimental Crystal Structure Determination

CCDC 2248363: Experimental Crystal Structure Determination

CCDC 2231851: Experimental Crystal Structure Determination

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