Improving the solubility of dexlansoprazole by cocrystallization with isonicotinamide

被引：21

作者：

Li, Jianhui ^{[1
,2
]}

Wang, Lianyan ^{[2
]}

Ye, Yue Qi ^{[3
]}

Fu, Xue ^{[2
]}

Ren, Qinghua ^{[1
]}

Zhang, Hailu ^{[2
]}

Deng, Zongwu ^{[2
]}

机构：

[1] Shanghai Univ, Coll Sci, Shanghai 200444, Peoples R China

[2] Chinese Acad Sci, Lab Magnet Resonance Spect & Imaging, Suzhou Inst Nanotech & Nanobion, Suzhou 215123, Peoples R China

[3] JEOL Beijing Co Ltd, Beijing 100190, Peoples R China

来源：

EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES | 2016年 / 85卷

关键词：

Pharmaceutical cocrystal; Proton-pump inhibitor; Dexlansoprazole; Intermolecular interaction; Solubilization; PHARMACEUTICAL COCRYSTALS; SOLID-STATE; LANSOPRAZOLE; STABILITY; FORMS; ACIDS; OMEPRAZOLE; CONTINUUM; SALTS;

D O I：

10.1016/j.ejps.2016.01.029

中图分类号：

R9 [药学];

学科分类号：

1007 ;

摘要：

Cocrystallization of an active pharmaceutical ingredient (API) with a cocrystal former (co-former) is widely used to tailor the physicochemical properties of parent APIs. For proton-pump inhibitors (PPIs), the isolation of cocrystals has not been widely investigated. Here, a 1:1 cocrystal of a PPI molecule, dexlansoprazole (DLS), was obtained by solvent crystallization with isonicotinamide (INM). The product was characterized by X-ray powder diffraction (XRPD), differential scanning calorimetry (DSC), solid-state and liquid NMR, as well as Fourier transform infrared spectroscopy (FTIR) techniques. A two-point R-2(2) (9) hetero-synthon was proposed to exist in the cocrystal, where intermolecular hydrogen bonding occurs between NH, SO groups of DLS and amide of INM. The dissolution profiles of DLS and DLS-INM in water were also collected, and the results demonstrate the cocrystal exhibits superior apparent maximum solubility relative to the pure drug. (C) 2016 Elsevier B.V. All rights reserved.

引用

页码：47 / 52

页数：6

共 47 条

[1] Do polymorphic compounds make good cocrystallizing agents?: A structural case study that demonstrates the importance of synthon flexibility [J].

Aakeröy, CB ;

Beatty, AM ;

Helfrich, BA ;

Nieuwenhuyzen, M .

CRYSTAL GROWTH & DESIGN, 2003, 3 (02) :159-165

[2] Solubility Advantage of Amorphous Drugs and Pharmaceutical Cocrystals [J].

Babu, N. Jagadeesh ;

Nangia, Ashwini .

CRYSTAL GROWTH & DESIGN, 2011, 11 (07) :2662-2679

[3] Pharmaceutical cocrystal and salts of norfloxacin [J].

Basavoju, Srinivas ;

Bostrom, Dan ;

Velaga, Sitaram P. .

CRYSTAL GROWTH & DESIGN, 2006, 6 (12) :2699-2708

[4]

Behm BW, 2011, EXPERT REV GASTROENT, V5, P439, DOI [10.1586/egh.11.37, 10.1586/EGH.11.37]

[5] Tape and layer structures in cocrystals of some di- and tricarboxylic acids with 4,4′-bipyridines and isonicotinamide.: From binary to ternary cocrystals [J].

Bhogala, BR ;

Basavoju, S ;

Nangia, A .

CRYSTENGCOMM, 2005, 7 :551-562

[6]

Braga D., 2011, Patent US, Patent No. [2011009637 A1, 2011009637]

[7] Pharmaceutical Cocrystals: A Novel Approach for Oral Bioavailability Enhancement of Drugs [J].

Chadha, Renu ;

Saini, Anupam ;

Arora, Poonam ;

Bhandari, Swati .

CRITICAL REVIEWS IN THERAPEUTIC DRUG CARRIER SYSTEMS, 2012, 29 (03) :183-218

[8] The salt-cocrystal continuum: The influence of crystal structure on ionization state [J].

Childs, Scott L. ;

Stahly, G. Patrick ;

Park, Aeri .

MOLECULAR PHARMACEUTICS, 2007, 4 (03) :323-338

[9]

Das S, 2009, ORIENT J CHEM, V25, P1129

[10] Degradation of lansoprazole and omeprazole in the aquatic environment [J].

DellaGreca, M. ;

Iesce, M. R. ;

Previtera, L. ;

Rubino, M. ;

Temussi, F. ;

Brigante, M. .

CHEMOSPHERE, 2006, 63 (07) :1087-1093

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