Diversity in Itraconazole Cocrystals with Aliphatic Dicarboxylic Acids of Varying Chain Length

Anna Shevchenko; Inna Miroshnyk; Lars-Olof Pietilä; Jorma Haarala; Jukka Salmia; Kai Sinervo; Sabiruddin Mirza; Bert van Veen; Erkki Kolehmainen; Nonappa Nonappa; Jouko Yliruusi

doi:10.1021/cg401061t

Diversity in Itraconazole Cocrystals with Aliphatic Dicarboxylic Acids of Varying Chain Length

Anna Shevchenko^*, Inna Miroshnyk, Lars-Olof Pietilä, Jorma Haarala, Jukka Salmia, Kai Sinervo, Sabiruddin Mirza, Bert van Veen, Erkki Kolehmainen, Nonappa Nonappa, Jouko Yliruusi

^*Corresponding author for this work

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

29 Citations (Scopus)

Abstract

The cocrystal formation potential of itraconazole, a potent antifungal drug, with C2-C10 aliphatic dicarboxylic acids has been investigated. Using two experimental screening techniques (solvent-assisted grinding and evaporation-based crystallization), the cocrystals of itraconazole with C2-C7 dicarboxylic acids have been successfully synthesized and characterized by powder X-ray diffraction, solid state nuclear magnetic resonance, Raman spectroscopy, and thermal analysis. The characterized multicomponent compounds include anhydrous cocrystals (malonic, succinic, glutaric, and pimelic acids), a cocrystal hydrate (adipic acid), and cocrystal solvates with acetone and tetrahydrofuran (oxalic acid). This study is the first to demonstrate the diversity in itraconazole cocrystals with a range of aliphatic dicarboxylic acids of variable carbon chain lengths.

Original language	English
Pages (from-to)	4877-4884
Number of pages	8
Journal	Crystal Growth and Design
Volume	13
Issue number	11
DOIs	https://doi.org/10.1021/cg401061t
Publication status	Published - Nov 2013
MoE publication type	A1 Journal article-refereed

Keywords

SOLID-STATE PROPERTIES
PHARMACEUTICAL COCRYSTALS
CO-CRYSTAL
SOLUBILITY ADVANTAGE
CARBOXYLIC-ACIDS
HYDROGEN-BONDS
DRUG
DISSOLUTION
IMPROVE
PHARMACOKINETICS

Access to Document

10.1021/cg401061t

Cite this

@article{d1270b796eaa4ff1b473cb551f86d87c,

title = "Diversity in Itraconazole Cocrystals with Aliphatic Dicarboxylic Acids of Varying Chain Length",

abstract = "The cocrystal formation potential of itraconazole, a potent antifungal drug, with C2-C10 aliphatic dicarboxylic acids has been investigated. Using two experimental screening techniques (solvent-assisted grinding and evaporation-based crystallization), the cocrystals of itraconazole with C2-C7 dicarboxylic acids have been successfully synthesized and characterized by powder X-ray diffraction, solid state nuclear magnetic resonance, Raman spectroscopy, and thermal analysis. The characterized multicomponent compounds include anhydrous cocrystals (malonic, succinic, glutaric, and pimelic acids), a cocrystal hydrate (adipic acid), and cocrystal solvates with acetone and tetrahydrofuran (oxalic acid). This study is the first to demonstrate the diversity in itraconazole cocrystals with a range of aliphatic dicarboxylic acids of variable carbon chain lengths.",

keywords = "SOLID-STATE PROPERTIES, PHARMACEUTICAL COCRYSTALS, CO-CRYSTAL, SOLUBILITY ADVANTAGE, CARBOXYLIC-ACIDS, HYDROGEN-BONDS, DRUG, DISSOLUTION, IMPROVE, PHARMACOKINETICS",

author = "Anna Shevchenko and Inna Miroshnyk and Lars-Olof Pietil{\"a} and Jorma Haarala and Jukka Salmia and Kai Sinervo and Sabiruddin Mirza and {van Veen}, Bert and Erkki Kolehmainen and Nonappa Nonappa and Jouko Yliruusi",

year = "2013",

month = nov,

doi = "10.1021/cg401061t",

language = "English",

volume = "13",

pages = "4877--4884",

journal = "Crystal Growth and Design",

issn = "1528-7483",

publisher = "AMERICAN CHEMICAL SOCIETY",

number = "11",

}

Diversity in Itraconazole Cocrystals with Aliphatic Dicarboxylic Acids of Varying Chain Length. / Shevchenko, Anna; Miroshnyk, Inna; Pietilä, Lars-Olof; Haarala, Jorma; Salmia, Jukka; Sinervo, Kai; Mirza, Sabiruddin; van Veen, Bert; Kolehmainen, Erkki; Nonappa, Nonappa; Yliruusi, Jouko.

In: Crystal Growth and Design, Vol. 13, No. 11, 11.2013, p. 4877-4884.

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

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T1 - Diversity in Itraconazole Cocrystals with Aliphatic Dicarboxylic Acids of Varying Chain Length

AU - Shevchenko, Anna

AU - Miroshnyk, Inna

AU - Pietilä, Lars-Olof

AU - Haarala, Jorma

AU - Salmia, Jukka

AU - Sinervo, Kai

AU - Mirza, Sabiruddin

AU - van Veen, Bert

AU - Kolehmainen, Erkki

AU - Nonappa, Nonappa

AU - Yliruusi, Jouko

PY - 2013/11

Y1 - 2013/11

N2 - The cocrystal formation potential of itraconazole, a potent antifungal drug, with C2-C10 aliphatic dicarboxylic acids has been investigated. Using two experimental screening techniques (solvent-assisted grinding and evaporation-based crystallization), the cocrystals of itraconazole with C2-C7 dicarboxylic acids have been successfully synthesized and characterized by powder X-ray diffraction, solid state nuclear magnetic resonance, Raman spectroscopy, and thermal analysis. The characterized multicomponent compounds include anhydrous cocrystals (malonic, succinic, glutaric, and pimelic acids), a cocrystal hydrate (adipic acid), and cocrystal solvates with acetone and tetrahydrofuran (oxalic acid). This study is the first to demonstrate the diversity in itraconazole cocrystals with a range of aliphatic dicarboxylic acids of variable carbon chain lengths.

AB - The cocrystal formation potential of itraconazole, a potent antifungal drug, with C2-C10 aliphatic dicarboxylic acids has been investigated. Using two experimental screening techniques (solvent-assisted grinding and evaporation-based crystallization), the cocrystals of itraconazole with C2-C7 dicarboxylic acids have been successfully synthesized and characterized by powder X-ray diffraction, solid state nuclear magnetic resonance, Raman spectroscopy, and thermal analysis. The characterized multicomponent compounds include anhydrous cocrystals (malonic, succinic, glutaric, and pimelic acids), a cocrystal hydrate (adipic acid), and cocrystal solvates with acetone and tetrahydrofuran (oxalic acid). This study is the first to demonstrate the diversity in itraconazole cocrystals with a range of aliphatic dicarboxylic acids of variable carbon chain lengths.

KW - SOLID-STATE PROPERTIES

KW - PHARMACEUTICAL COCRYSTALS

KW - CO-CRYSTAL

KW - SOLUBILITY ADVANTAGE

KW - CARBOXYLIC-ACIDS

KW - HYDROGEN-BONDS

KW - DRUG

KW - DISSOLUTION

KW - IMPROVE

KW - PHARMACOKINETICS

U2 - 10.1021/cg401061t

DO - 10.1021/cg401061t

M3 - Article

VL - 13

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EP - 4884

JO - Crystal Growth and Design

JF - Crystal Growth and Design

SN - 1528-7483

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ER -