Determination of Solubility Parameters of Ibuprofen and Ibuprofen Lysinate

In recent years there has been a growing interest in formulating solid dispersions, which purposes mainly include solubility enhancement, sustained drug release and taste masking. The most notable problem by these dispersions is drug-carrier (in)solubility. Here we focus on solubility parameters as a tool for predicting the solubility of a drug in certain carriers. Solubility parameters were determined in two different ways: solely by using calculation methods, and by experimental approaches. Six different calculation methods were applied in order to calculate the solubility parameters of the drug ibuprofen and several excipients. However, we were not able to do so in the case of ibuprofen lysinate, as calculation models for salts are still not defined. Therefore, the extended Hansen’s approach and inverse gas chromatography (IGC) were used for evaluating of solubility parameters for ibuprofen lysinate. The obtained values of the total solubility parameter did not differ much between the two methods: by the extended Hansen’s approach it was δt = 31.15 MPa0.5 and with IGC it was δt = 35.17 MPa0.5. However, the values of partial solubility parameters, i.e., δd, δp and δh, did differ from each other, what might be due to the complex behaviour of a salt in the presence of various solvents.

[1]  C. Hansen,et al.  The three-dimensional solubility parameter - key to paint component affinities: solvents, plasticizers, polymers, and resins. II. Dyes, emulsifiers, mutual solubility and compatibility, and pigments. III. Independent cal-culation of the parameter components , 1967 .

[2]  E. B. Bagley,et al.  Three-dimensional solubility parameters and their relationship to internal pressure measurements in polar and hydrogen bonding solvents , 1971 .

[3]  A. Voelkel,et al.  New procedure for the determination of Hansen solubility parameters by means of inverse gas chromatography. , 2008, Journal of chromatography. A.

[4]  许旱峤,et al.  Kirk-Othmer Encyclopedia of Chemical Technology数据库介绍及实例 , 2007 .

[5]  Xing Tang,et al.  In vitro and in vivo evaluation of fenofibrate solid dispersion prepared by hot-melt extrusion , 2010, Drug development and industrial pharmacy.

[6]  C. Hansen,et al.  The Universality of the Solubility Parameter , 1969 .

[7]  M. Chaudhury,et al.  Monopolar surfaces. , 1987, Advances in colloid and interface science.

[8]  A. Voelkel,et al.  Characterization of the interactions in polymer-filler systems by inverse gas chromatography. , 2001, Journal of Chromatography A.

[9]  Emmanuel Stefanis,et al.  Prediction of Hansen Solubility Parameters with a New Group-Contribution Method , 2008 .

[10]  A. Voelkel,et al.  Inverse gas chromatography in the examination of organic compounds: Polarity and solubility parameters of isoquinoline derivatives , 1998 .

[11]  A. V. Kiselev,et al.  Gas-adsorption chromatography , 1969 .

[12]  J. Breitkreutz,et al.  Improved group contribution parameter set for the application of solubility parameters to melt extrusion. , 2013, European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V.

[13]  R. F. Fedors,et al.  A method for estimating both the solubility parameters and molar volumes of liquids , 1974 .

[14]  K. Héberger,et al.  Selection of solubility parameters for characterization of pharmaceutical excipients. , 2007, Journal of chromatography. A.

[15]  R. Manavalan,et al.  Extended Hansen's solubility approach: meloxicam in individual solvents. , 2007, Pakistan journal of pharmaceutical sciences.

[16]  C. Hansen,et al.  The Three Dimensional Solubility Parameter-Key to Paint Component Affinities : II. Dies, Emulsifiers, Mutual Solubility and Compatibility, and Pigments , 1967 .

[17]  Peter York,et al.  The use of solubility parameters in pharmaceutical dosage form design , 1997 .

[18]  P York,et al.  Solubility parameters as predictors of miscibility in solid dispersions. , 1999, Journal of pharmaceutical sciences.

[19]  A. Voelkel,et al.  Solubility parameters of broad and narrow distributed oxyethylates of fatty alcohols , 1993 .

[20]  A. Güner The algorithmic calculations of solubility parameter for the determination of interactions in dextran/certain polar solvent systems , 2004 .

[21]  A. Beerbower,et al.  Expanded solubility parameter approach. I: Naphthalene and benzoic acid in individual solvents. , 1984, Journal of pharmaceutical sciences.

[22]  F. Fowkes Dispersion Force Contributions to Surface and Interfacial Tensions, Contact Angles, and Heats of Immersion , 1964 .

[23]  Van Krevelen Properties of Polymers: Their Correlation with Chemical Structure; their Numerical Estimation and Prediction from Additive Group Contributions , 2009 .

[24]  C. Hansen Hansen Solubility Parameters: A User's Handbook , 1999 .

[25]  Chandra Vemavarapu,et al.  Use of surfactants as plasticizers in preparing solid dispersions of poorly soluble API: selection of polymer-surfactant combinations using solubility parameters and testing the processability. , 2007, International journal of pharmaceutics.

[26]  T. Rades,et al.  Selection of excipients for melt extrusion with two poorly water-soluble drugs by solubility parameter calculation and thermal analysis. , 2001, International journal of pharmaceutics.

[27]  Xing Tang,et al.  Part I: Characterization of Solid Dispersions of Nimodipine Prepared by Hot-melt Extrusion , 2007, Drug development and industrial pharmacy.

[28]  Christine Allen,et al.  Polymer-drug compatibility: a guide to the development of delivery systems for the anticancer agent, ellipticine. , 2004, Journal of pharmaceutical sciences.

[29]  B. Strzemięcka,et al.  Determination of Hansen solubility parameters of solid materials by inverse gas-solid chromatography , 2008 .

[30]  The modified extended Hansen method to determine partial solubility parameters of drugs containing a single hydrogen bonding group and their sodium derivatives: benzoic acid/Na and ibuprofen/Na. , 2000, International journal of pharmaceutics.

[31]  S. Hoag,et al.  Influence of various drugs on the glass transition temperature of poly(vinylpyrrolidone): a thermodynamic and spectroscopic investigation. , 2001, International journal of pharmaceutics.

[32]  Jessica Albers Hot-melt extrusion with poorly soluble drugs , 2008 .

[33]  R. Chokshi,et al.  Characterization of physico-mechanical properties of indomethacin and polymers to assess their suitability for hot-melt extrusion processs as a means to manufacture solid dispersion/solution. , 2005, Journal of pharmaceutical sciences.

[34]  Joel H. Hildebrand,et al.  The solubility of nonelectrolytes , 1964 .

[35]  S. Velaga,et al.  Hansen solubility parameter as a tool to predict cocrystal formation. , 2011, International journal of pharmaceutics.

[36]  A. Voelkel,et al.  Inverse gas chromatographic determination of solubility parameters of excipients. , 2005, International journal of pharmaceutics.

[37]  C. Hansen,et al.  The three dimensional solubility parameter - key to paint component affinities: I. Solvents, plasticizers, polymers, and resins , 1967 .