Manufacture and performance evaluation of a stable amorphous complex of an acidic drug molecule and Neusilin.

In this paper, we explore the use of Neusilin, an inorganic magnesium aluminometasilicate, to stabilize the amorphous form of an acidic drug Sulindac. Both cryomilling and ball milling of the drug with Neusilin were found to produce the amorphous phase. However, the ball-milled (BM) material exhibited superior physical stability when compared with the cryomilled material at 40°C/75% relative humidity. (13) C solid-state nuclear magnetic resonance investigation of the BM material revealed an acid-base reaction between Sulindac and Neusilin. Optimal milling conditions and the kinetics of salt formation were also established. As benchtop milling is a laboratory-scale process, a scalable process was developed to make Sulindac-Neusilin amorphous drug complex using hot-melt extrusion (HME). The dissolution properties of the resulting HME material was found to have been improved over the material made by benchtop milling while maintaining similar physical stability. The HME material was used to make tablets using a direct compression method. The HME tablets were found to have better dissolution properties than tablets made from crystalline Sulindac. For the broad class of acidic drugs containing the carboxyl moiety, inorganic silicates such as Neusilin would offer a better choice than organic polymers to stabilize the amorphous phase.

[1]  N Kaneniwa,et al.  Effect of environmental temperature on polymorphic solid-state transformation of indomethacin during grinding. , 1986, Chemical & pharmaceutical bulletin.

[2]  R. Glen,et al.  A new method for the reproducible generation of polymorphs: two forms of sulindac with very different solubilities , 2007 .

[3]  A. Van Schepdael,et al.  Characterization of ternary solid dispersions of Itraconazole in polyethylene glycol 6000/polyvidone-vinylacetate 64 blends. , 2008, European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V.

[4]  Shigeo Kojima,et al.  Ability of polyvinylpyrrolidone and polyacrylic acid to inhibit the crystallization of amorphous acetaminophen. , 2004, Journal of pharmaceutical sciences.

[5]  A. Saha,et al.  Formation of physically stable amorphous phase of ibuprofen by solid state milling with kaolin. , 2008, European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V.

[6]  L Yu,et al.  Amorphous pharmaceutical solids: preparation, characterization and stabilization. , 2001, Advanced drug delivery reviews.

[7]  M. Senna,et al.  Prediction of apparent equilibrium solubility of indomethacin compounded with silica by 13C solid state NMR. , 2002, International journal of pharmaceutics.

[8]  R. Bogner,et al.  Amorphization Alone Does Not Account for the Enhancement of Solubility of Drug Co-ground with Silicate: The Case of Indomethacin , 2008, AAPS PharmSciTech.

[9]  K. Johnston,et al.  Dissolution Rates and Supersaturation Behavior of Amorphous Repaglinide Particles Produced by Controlled Precipitation , 2007 .

[10]  L. S. Taylor,et al.  Phase behavior of poly(vinylpyrrolidone) containing amorphous solid dispersions in the presence of moisture. , 2009, Molecular pharmaceutics.

[11]  M. C. Martínez‐Ohárriz,et al.  Polymorphism of sulindac: isolation and characterization of a new polymorph and three new solvates. , 1997, Journal of pharmaceutical sciences.

[12]  Lynne S Taylor,et al.  Effect of polymer type on the dissolution profile of amorphous solid dispersions containing felodipine. , 2008, European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V.

[13]  M. Senna,et al.  Solid State Radical Recombination and Charge Transfer across the Boundary between Indomethacin and Silica under Mechanical Stress , 2002 .

[14]  Y. Guo,et al.  Physical characteristics and chemical degradation of amorphous quinapril hydrochloride. , 2000, Journal of pharmaceutical sciences.

[15]  V. Caron,et al.  Transformation of pharmaceutical compounds upon milling and comilling: the role of T(g). , 2007, Journal of pharmaceutical sciences.

[16]  D. Law,et al.  Ritonavir-PEG 8000 amorphous solid dispersions: in vitro and in vivo evaluations. , 2004, Journal of pharmaceutical sciences.

[17]  Karthik Nagapudi,et al.  Amorphous Active Pharmaceutical Ingredients in Preclinical Studies: Preparation, Characterization, and Formulation , 2008 .

[18]  A. Serajuddin,et al.  Solid dispersion of poorly water-soluble drugs: early promises, subsequent problems, and recent breakthroughs. , 1999, Journal of pharmaceutical sciences.

[19]  Ping Gao,et al.  Enhanced bioavailability of a poorly soluble VR1 antagonist using an amorphous solid dispersion approach: a case study. , 2008, Molecular pharmaceutics.

[20]  Jan Van Humbeeck,et al.  Influence of Preparation Methods on Solid State Supersaturation of Amorphous Solid Dispersions: A Case Study with Itraconazole and Eudragit E100 , 2010, Pharmaceutical Research.

[21]  G. Zografi,et al.  Cryogenic grinding of indomethacin polymorphs and solvates: assessment of amorphous phase formation and amorphous phase physical stability. , 2002, Journal of pharmaceutical sciences.

[22]  Ping Gao,et al.  Characterization and optimization of AMG 517 supersaturatable self-emulsifying drug delivery system (S-SEDDS) for improved oral absorption. , 2009, Journal of pharmaceutical sciences.

[23]  Ping Gao,et al.  Enhanced Oral Bioavailability of a Poorly Water Soluble Drug PNU‐91325 by Supersaturatable Formulations , 2004, Drug development and industrial pharmacy.

[24]  P. Gao,et al.  Development of a supersaturable SEDDS (S-SEDDS) formulation of paclitaxel with improved oral bioavailability. , 2003, Journal of pharmaceutical sciences.

[25]  J. Parikh,et al.  Preparation and Characterization of Co-Grinded Mixtures of Aceclofenac and Neusilin US2 for Dissolution Enhancement of Aceclofenac , 2009, AAPS PharmSciTech.

[26]  M. Kinoshita,et al.  Improvement of solubility and oral bioavailability of a poorly water-soluble drug, TAS-301, by its melt-adsorption on a porous calcium silicate. , 2002, Journal of pharmaceutical sciences.

[27]  Deepak Bahl,et al.  Amorphization of Indomethacin by Co-Grinding with Neusilin US2: Amorphization Kinetics, Physical Stability and Mechanism , 2006, Pharmaceutical Research.

[28]  M Ikeda,et al.  Stability of amorphous indomethacin compounded with silica. , 2001, International journal of pharmaceutics.

[29]  R. Bogner,et al.  Formation of physically stable amorphous drugs by milling with Neusilin. , 2003, Journal of pharmaceutical sciences.