Computation of Solubility parameters using Molecular. dynamics simulation

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1 Appendix I Appendix I Computation of Solubility parameters using Molecular dynamics simulation Computational Methods Molecular dynamics (MD) simulations were carried out using the Accelrys Materials Studio[1] (Version 7.0) [2] for tacrolimus. The crystal structure (Fig. 1 a) was obtained from the Cambridge Structural Database, Ver The space group of the crystal is P (orthorhombic with the unit cell dimensions of a = Å, b = Å, c = Å, and Z = 4). The crystal structure was extended to 3 x 3 x 2 unit cells (72 tacrolimus molecules). The COMPASS [3] (condensed-phase optimized molecular potentials for the atomistic simulation studies) force field was used to model the atomic interactions for tacrolimus molecules. COMPASS force field model gives densities of g/cm 3 for pure tacrolimus. The integration time step used was 1 fs. Ewald summation was used to enable the long range interactions. A cutoff radius of 12.5 Å was used for both non-bonded and electrostatic interactions. Simulation in the NPT (constant number of particle, constant pressure, and constant temperature) ensemble was conducted at 298 K for 2 ns to ensure that tacrolimus system reaches equilibration condition. The equilibrated amorphous cell of tacrolimus is shown in Figure 1b. Equilibration was determined by observing the change in the thermodynamic properties (energies, temperatures, and densities) as a function of time. The system was concluded to have reached equilibration condition if these properties showed sufficiently small variations over time. The required time was less than 100 ps. The Nose/Hoover [4] thermostat and Berendsen barostat [5] were used to control the temperature and pressure, respectively. The production run was done by choosing three different

2 Appendix I trajectories (at time step of 1 ns, 1.5 ns, and 2 ns) from the equilibrated system. Energy minimization was then performed for the three sets of data, followed by MD simulation in NVT (isothermal) ensemble at 298 K for 100 ps. The final 50 ps was used to calculate the Hansen solubility parameter. The three data sets were then averaged to obtain the solubility parameter for tacrolimus.

3 Appendix I Hansen solubility parameter Drug / Polymer Solubility Parameter (δt; MPa 1/2 ) Difference in Solubility Parameter between TAC and polymer (Δδt; MPa 1/2 ) TAC 19.1 PVP-VA Soluplus HPC Table 1: Calculated Solubility Parameters for tacrolimus and polymers The solid-solid miscibility of drug and polymers can be predicted by calculating Hansen solubility parameters (δt) from the chemical structure. The solubility parameter of tacrolimus was calculated using molecular dynamic simulation using the method reported by Gupta and

4 Appendix I coworkers [6]. The difference between the solubility parameters (Δδt) of two materials is known as interaction parameter and is indicative of likely miscibility or immiscibility. Compounds with Δδt value 7.0 MPa 1/2 or less are most likely to be miscible whereas compounds with value 10.0 MPa 1/2 are most likely immiscible [7]. The interaction parameter (Δδt) for tacrolimus and the polymers (PVP VA64, Soluplus) is less than 1, so it is most likely that drug and polymer melt will be miscible during melt extrusion. References 1. Materials Studio Modeling. Accelrys Software Inc. : San Diego, CA. 2. Nassar, T., et al., A novel nanocapsule delivery system to overcome intestinal degradation and drug transport limited absorption of P-glycoprotein substrate drugs. Pharm. Res., (9): p Sun, H., COMPASS: An ab Initio Force-Field Optimized for Condensed-Phase Applications- Overview with Details on Alkane and Benzene Compounds. J. Phys. Chem. B (38): p Frenkel, D. and B. Smit, Understanding Molecular Simulation. second ed. ed. 2002, San Deigo CA: Academic Press. 5. Berendsen, H.J.C., et al., Molecular dynamics with coupling to an external bath. J. Chem. Phys., : p Gupta, J., et al., Prediction of solubility parameters and miscibility of pharmaceutical compounds by molecular dynamics simulations. J. Phys. Chem. B, (9): p Greenhalgh, D.J., et al., Solubility parameters as predictors of miscibility in solid dispersions. J. Pharm. Sci., (11): p

5 Appendix II Appendix II Extrusion of blank films Hydrophilic polymers that had been previously used in extrusion were extruded with a few plasticizers to determine the ideal temperature ranges for extrusion into thin flexible films. The extrusion conditions, the excipients used and the appearance and nature of the extruded film are discussed below. A polyvinyl pyrrolidone polymer (Kollidon 30) and polyethylene glycol 400 (PEG 400) were extruded at a screw speed of 100 rpm and the conditions shown below, and a slightly yellow, translucent, brittle film was obtained. Temperature ( o C) Unused Feed Heating Mixing Conveying Shaping Die Table 1:Extrusion conditions for Kollidon 30 films Combination of poly vinyl pyrrolidone (Kollidon VA64) and polyethylene glycol (400 & 6000) was extruded to observe its film forming ability and the nature of the films on storage. The polyvinyl pyrrolidone used was from BASF under the commercial name Kollidon VA 64. The physical mixture was ground in a mortar and pestle to get a uniform mixture of the components. Another polymer considered to be a film former, a graft co polymer of polyvinyl alcohol and poly ethylene glycol (Kollicoat IR) was extruded to give a thin, slightly yellow coloured, transparent flexible film which became

6 Appendix II sticky on storage at ambient. The extruder conditions required for this polymer to form a film are given below. Temperature ( o C) Unused Feed Heating Mixing Conveying Shaping Die Table 2: Extrusion conditions for Kollicoat IR films High molecular weight acrylic acid polymer crosslinked with divinly glycol (Noveon AA1 Polycarbophil) was known to have good bioadhesive properties which could be an effective way of adhering to a mucous membrane. The pure material did not melt in the barrel of the extruder till 180 o C and started charring on increasing the temperature above that. This showed that poly acrylic acid was not suited for use as a major component in the film at the temperature range used (160 o C o C). The use of poly acrylic acid as a part of the formulation along with other excipients was investigated. HPMC and HPC have been used to prepare films using solvent casting. Their suitability for use in melt extrusion was checked. From the above extrusions the temperature profiles suitable for the extrusion of these polymer and plasticizer combinations into flexible films was observed. The films containing cellulose had a grainy texture while those containing Kollidon VA 64 were glassy in appearance.

7 Appendix II Selected trials with PVP VA64 Run Other Nature of film Carrier / Matrix number Excipients After Extrusion On Storage Film could not be extruded as 1 Kollidon VA 64 the Extruder PEG 400 material formed a pasty lump on (20% w/w) mixing and could not be fed into 2 Kollidon VA 64 The extrudate The flakes that was in the form were extruded of flakes due to PEG 6000 were found to incomplete (20% w/w) become brittle melting of on storage at material in the ambient barrel 3 Kollidon VA 64 Sticky on PEG 400 Transparent, exposure to (10% w/w) brittle film moisture 4 Kollidon VA 64 Transparent, Brittle on PEG 400 slightly flexible storage in <15% (12% w/w) film RH 5 Kollidon VA 64 Transparent, sticky film, Brittle on PEG 400 flexible when storage in <15% (15% w/w) thin, brittle RH when thick. 6 Kollidon VA 64 A glassy brittle Slightly sticky TEC film was on exposure to (2% w/w) obtained moisture 7 Kollidon VA 64 A glassy brittle Slightly sticky (93% w/w) TEC film was on exposure to Carbomer (5% (2% w/w) obtained moisture w/w) Table 3: Films with PVP VA64 as carrier polymer

8 Appendix II Selected trials with HPC and HPMC Run Other Nature of film Carrier / Matrix number Excipients After Extrusion On Storage There was no 1 A translucent observed loss in HPC:HPMC TEC flexible film was flexibility or (4:1) (2% w/w) obtained visible change in the film The product remained in powder form in Product 2 HPMC TEC the barrel and remained (2% w/w) was stuck in the unchanged on die. Hence storage extrusion was not done HPC:HPMC An opaque Product 3 (1:1) TEC slight brown remained Carbomer (5% (2% w/w) flexible film was unchanged on w/w) obtained. storage An opaque Product 4 HPC:HPMC TEC brown flexible remained (1:1) (2% w/w) film was unchanged on obtained. storage 5 An opaque Product HPC:HPMC: TEC slight brown remained Carbomer (2% w/w) flexible film was unchanged on (6:3:1) obtained. storage Table 4: Films with HPC and HPMC as carrier polymer

9 Appendix III Appendix III Films of HPC containing milled and crystalline Sirolimus Extrusion Films of HPC containing both milled and crystalline Sirolimus with TPGS and TEC as plasticizers were extruded. Experiment no Sirolimus HPC TPGS TEC H1 Milled 5% 75% 5% 5% H2 Crystalline 5% 75% 5% 5% Table 1: Composition of physical mixtures Tape Die Chill rolls o C 75 o C 85 o C 90 o C 90 o C Table 2: Extruder conditions Screw Speed: 100rpm Feed: Manual feeding at 3 Translucent white, flexible and strong films were obtained. They were viewed under polarised light to check for presence of crystalline drug. The extruded film with crystalline sirolimus showed presence of sirolimus crystals (Fig. 1).

10 Intensity (a.u.) Appendix III Figure 1: Films as viewed under polarised light (a) Blank film, (b) film containing crystalline sirolimus, H2 and (c) film containing milled sirolimus, H1 The XRD of the films was done to confirm the physical form of sirolimus in extruded films and diffraction pattern of extruded films with crystalline sirolimus showed the peaks similar to physical mixture in the case of H2 and no re-crystallization of drug during extrusion for formulation H1 (Fig. 2). (a) (b) (c) (d) (e) Sirolimus SRM-HPC PM Milled SRM-HPC PM SRM-HPC film Milled SRM-HPC film (a) (b) (c) (d) (e) Figure 2: XRD results of HPC films (H1, H2) and physical mixtures The dissolution testing of the extruded films show that H1 shows higher rate and percentage of dissolution compared to H2 due to the higher solubility of milled sirolimus. HPC is a slow dissolving polymer and the films exhibit a dissolution profile dependant on the erosion of the polymeric film.

11 Drug content (%) Dissolution (%) Appendix III SRM HPC film MSRM HPC film Time (minute) Figure 3: Dissolution of HPC films (H1 and H2) The films were stored at 40 o C and 75% RH to study their stability. The physical integrity of the HPC films was good as the films remain flexible, intact and firm. The stability of encapsulated sirolimus was significantly enhanced as shown in Fig. 4 below. 120 Initial 1 month 2 month 4 month 6 month SRM HPC film MSRM HPC film BMSRM

12 Appendix III Figure 4: Stability of HPC films containing milled and crystalline sirolimus stored at 40 C / 75% RH % Sample Day 45 Day 75 Degradation H1 83% 72% 28% H2 89% 76% 24% Ball Milled SRM 4.2% 2% 98% Table 3: Extruder conditions The films do not melt or lose their structure when stored at 40 o C and 75% RH in closed bottles.

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