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Dimorphism of the prodrug L-tyrosine ethyl ester: pressure-temperature state diagram and crystal structure of phase II

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Standard

Dimorphism of the prodrug L-tyrosine ethyl ester : pressure-temperature state diagram and crystal structure of phase II. / Rietveld, Ivo B; Barrio, Maria; Tamarit, Josep-Lluís; Nicolaï, Béatrice; Van de Streek, Jacco; Mahé, Nathalie; Ceolin, René; Do, Bernard.

I: Journal of Pharmaceutical Sciences, Bind 100, Nr. 11, 2011, s. 4774-82.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

Harvard

Rietveld, IB, Barrio, M, Tamarit, J-L, Nicolaï, B, Van de Streek, J, Mahé, N, Ceolin, R & Do, B 2011, 'Dimorphism of the prodrug L-tyrosine ethyl ester: pressure-temperature state diagram and crystal structure of phase II', Journal of Pharmaceutical Sciences, bind 100, nr. 11, s. 4774-82. https://doi.org/10.1002/jps.22672

APA

Rietveld, I. B., Barrio, M., Tamarit, J-L., Nicolaï, B., Van de Streek, J., Mahé, N., ... Do, B. (2011). Dimorphism of the prodrug L-tyrosine ethyl ester: pressure-temperature state diagram and crystal structure of phase II. Journal of Pharmaceutical Sciences, 100(11), 4774-82. https://doi.org/10.1002/jps.22672

Vancouver

Rietveld IB, Barrio M, Tamarit J-L, Nicolaï B, Van de Streek J, Mahé N o.a. Dimorphism of the prodrug L-tyrosine ethyl ester: pressure-temperature state diagram and crystal structure of phase II. Journal of Pharmaceutical Sciences. 2011;100(11):4774-82. https://doi.org/10.1002/jps.22672

Author

Rietveld, Ivo B ; Barrio, Maria ; Tamarit, Josep-Lluís ; Nicolaï, Béatrice ; Van de Streek, Jacco ; Mahé, Nathalie ; Ceolin, René ; Do, Bernard. / Dimorphism of the prodrug L-tyrosine ethyl ester : pressure-temperature state diagram and crystal structure of phase II. I: Journal of Pharmaceutical Sciences. 2011 ; Bind 100, Nr. 11. s. 4774-82.

Bibtex

@article{33e398ba71424e1b859b9caedfdc9fae,
title = "Dimorphism of the prodrug L-tyrosine ethyl ester: pressure-temperature state diagram and crystal structure of phase II",
abstract = "Polymorphism is important in the field of solid-state behavior of drug molecules because of the continuous drive for complete control over drug properties. By comparing different structures of a series of L-tyrosine alkyl esters, it became apparent that the ethyl ester possesses dimorphism. Its structure was determined by powder diffraction and verified by density functional theory calculations; it is orthorhombic, P2(1) 2(1) 2(1) with a = 12.8679(8) {\AA}, b = 14.7345(7) {\AA}, c = 5.8333 (4) {\AA}, V = 1106.01(11) {\AA}, and Z = 4. The density of phase II is in line with other tyrosine alkyl esters and its conformation is similar to that of l-tyrosine methyl ester. The hydrogen bonds exhibit similar geometries for phase I and phase II, but the H-bonds in phase I are stronger. The solid II-solid I transition temperature is heating-rate dependent; it levels off at heating rates below 0.5 K min(-1), leading to a transition temperature of 306 ± 4 K. Application of the Clapeyron equation in combination with calorimetric and X-ray data has led to a topological diagram providing the relative stabilities of the two solid phases as a function of pressure and temperature; phase II is stable under ambient conditions.",
author = "Rietveld, {Ivo B} and Maria Barrio and Josep-Llu{\'i}s Tamarit and B{\'e}atrice Nicola{\"i} and {Van de Streek}, Jacco and Nathalie Mah{\'e} and Ren{\'e} Ceolin and Bernard Do",
note = "Copyright {\circledC} 2011 Wiley-Liss, Inc.",
year = "2011",
doi = "10.1002/jps.22672",
language = "English",
volume = "100",
pages = "4774--82",
journal = "Journal of Pharmaceutical Sciences",
issn = "0022-3549",
publisher = "Elsevier",
number = "11",

}

RIS

TY - JOUR

T1 - Dimorphism of the prodrug L-tyrosine ethyl ester

T2 - pressure-temperature state diagram and crystal structure of phase II

AU - Rietveld, Ivo B

AU - Barrio, Maria

AU - Tamarit, Josep-Lluís

AU - Nicolaï, Béatrice

AU - Van de Streek, Jacco

AU - Mahé, Nathalie

AU - Ceolin, René

AU - Do, Bernard

N1 - Copyright © 2011 Wiley-Liss, Inc.

PY - 2011

Y1 - 2011

N2 - Polymorphism is important in the field of solid-state behavior of drug molecules because of the continuous drive for complete control over drug properties. By comparing different structures of a series of L-tyrosine alkyl esters, it became apparent that the ethyl ester possesses dimorphism. Its structure was determined by powder diffraction and verified by density functional theory calculations; it is orthorhombic, P2(1) 2(1) 2(1) with a = 12.8679(8) Å, b = 14.7345(7) Å, c = 5.8333 (4) Å, V = 1106.01(11) Å, and Z = 4. The density of phase II is in line with other tyrosine alkyl esters and its conformation is similar to that of l-tyrosine methyl ester. The hydrogen bonds exhibit similar geometries for phase I and phase II, but the H-bonds in phase I are stronger. The solid II-solid I transition temperature is heating-rate dependent; it levels off at heating rates below 0.5 K min(-1), leading to a transition temperature of 306 ± 4 K. Application of the Clapeyron equation in combination with calorimetric and X-ray data has led to a topological diagram providing the relative stabilities of the two solid phases as a function of pressure and temperature; phase II is stable under ambient conditions.

AB - Polymorphism is important in the field of solid-state behavior of drug molecules because of the continuous drive for complete control over drug properties. By comparing different structures of a series of L-tyrosine alkyl esters, it became apparent that the ethyl ester possesses dimorphism. Its structure was determined by powder diffraction and verified by density functional theory calculations; it is orthorhombic, P2(1) 2(1) 2(1) with a = 12.8679(8) Å, b = 14.7345(7) Å, c = 5.8333 (4) Å, V = 1106.01(11) Å, and Z = 4. The density of phase II is in line with other tyrosine alkyl esters and its conformation is similar to that of l-tyrosine methyl ester. The hydrogen bonds exhibit similar geometries for phase I and phase II, but the H-bonds in phase I are stronger. The solid II-solid I transition temperature is heating-rate dependent; it levels off at heating rates below 0.5 K min(-1), leading to a transition temperature of 306 ± 4 K. Application of the Clapeyron equation in combination with calorimetric and X-ray data has led to a topological diagram providing the relative stabilities of the two solid phases as a function of pressure and temperature; phase II is stable under ambient conditions.

U2 - 10.1002/jps.22672

DO - 10.1002/jps.22672

M3 - Journal article

C2 - 21698599

VL - 100

SP - 4774

EP - 4782

JO - Journal of Pharmaceutical Sciences

JF - Journal of Pharmaceutical Sciences

SN - 0022-3549

IS - 11

ER -

ID: 44254142