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Original: publisher page

Hitesh S. Purohit, Lynne S. Taylor* · Pharmaceutical Research (Pharm Res), published online 27 September 2017; volume and page numbers not printed in this version (2017)

Phase Behavior of Ritonavir Amorphous Solid Dispersions during Hydration and Dissolution

Water splits ritonavir dispersions in PVP or PVPVA into drug-rich and polymer-rich phases, and once split they release drug slowly and form no nanodroplets, whereas HPMCAS dispersions stay mixed and release drug with the polymer fast enough to exceed the amorphous solubility at every loading tested.

Abbreviations

AAPS amorphous-amorphous phase separation; AFM atomic force microscopy; ASD amorphous solid dispersion; DL drug loading (wt% RTV in the dry ASD; a ratio such as 10:90 is RTV:polymer by weight); DSC differential scanning calorimetry; HPMCAS hydroxypropyl methylcellulose acetate succinate (MF grade); I/III ratio of the first to the third vibronic emission peak of pyrene (higher = more polar surroundings); LLPS liquid-liquid phase separation; NTA nanoparticle tracking analysis; PLM polarized light microscopy; PVP polyvinylpyrrolidone K-90; PVPVA polyvinylpyrrolidone vinyl acetate; RH relative humidity; RTV ritonavir; SEM scanning electron microscopy; Tg glass transition temperature; pdf p. = page of the PDF (the article prints no page numbers).

Story. Why they did it → how → what they found → how it fits together → what is left. Each part opens with the short version; "More detail" under it gives the full account. Grey ids open the evidence behind a sentence.

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Question

How do drug loading and polymer type change what happens inside a ritonavir ASD when it meets water, and how does that change dissolution, supersaturation and nanodroplet formation?

Short answer

Humidity split PVP and PVPVA dispersions at all loadings but no HPMCAS dispersion, and in buffer the 50% DL PVP and PVPVA films split within 10 s. ····· Only dispersions that stayed mixed exceeded the amorphous solubility (about 27–28 µg/mL) and formed nanodroplets: fresh PVP at 10–20% DL, fresh PVPVA at 10% DL and HPMCAS at every loading, fresh or humidity-exposed. ····

Conclusion

For ritonavir dispersions in PVP, PVPVA or HPMCAS at 10–50% DL, dissolved as films in pH 6.8 buffer at 25 °C, the authors conclude that dissolution "appears to depend" on a race between dissolution and phase separation in the wet matrix (abstract: "is governed"). · A matrix that has phase separated, through humidity or within seconds of water contact at high loading with PVP or PVPVA, loses its polymer quickly and releases drug under drug control at or below the amorphous solubility, so no nanodroplets form. ·· Only matrices that remain miscible during early dissolution release drug with the polymer and undergo LLPS; HPMCAS dispersions did so at every loading, also after humidity storage. ·· The resistance of HPMCAS to phase separation is "expected" from its lower hygroscopicity and its hydrogen-bond donors, but water uptake, hydrogen bonding and interaction parameters were not measured. · The nanodroplets are "likely" formed by LLPS from the supersaturated solution rather than released from matrix domains, an argument that rests on uniform low-loading films after 10 s in buffer and on matrix domains being far larger than the droplets. · The two rates in the proposed race were not measured during dissolution, and the authors recommend dispersions that resist phase separation and dissolve under polymer control. ·

01Why this study

Known 1Water can split an ASD

Absorbed water can separate drug and polymer into amorphous drug-rich and drug-lean domains (AAPS), which can speed crystallization; its effect on dissolution was unknown.

Rumondor 2009, ref 6; Rumondor 2011, ref 7

Known 2Supersaturation has a ceiling

Above the amorphous solubility the drug undergoes LLPS into drug-rich droplets of about 200–500 nm, and the solution stays at the amorphous solubility.

Ilevbare 2013, ref 9 ·

Known 3Low loading gives polymer-controlled release

At about 10% DL the dissolving polymer carries the drug out; at about 50% DL a drug-rich surface layer controls slower release.

Simonelli 1969, ref 36 ·

Known 4A rival origin for nanodroplets

Harmon et al. proposed that nanodroplets form inside the matrix by AAPS and are then released.

Harmon 2016, ref 29

Known 5High-loading ritonavir ASDs split in seconds

50% DL ritonavir dispersions in PVP or PVPVA phase separate within 10 s in water.

Purohit 2015, ref 14

Gap → this paperHow does AAPS in the wet matrix change dissolution and supersaturation, and do the nanodroplets come from the matrix or from the solution?
More detail

What was already known. The introduction and discussion build on these points:

  • The amorphous advantage and its cost. The amorphous form has a higher free energy and solubility than the crystal but a driving force to crystallize; compatible hydrophilic polymers can prevent crystallization and improve dissolution. (Hancock 1997, ref 3; Murdande 2010, ref 4; Vasconcelos 2007, ref 5)
  • Water-induced AAPS. In a hydrated ASD the drug can separate into amorphous drug-rich and drug-lean domains; AAPS can lead to crystallization because the polymer's inhibition is lost, while crystallization can also occur without AAPS through water-enhanced mobility. Sorbed water raises mobility and lowers Tg and viscosity, and AAPS has been suggested to precede crystallization; the impact of AAPS on dissolution was unknown. (Rumondor 2009, ref 6; Rumondor 2011, ref 7; Rumondor 2009, ref 8; Andronis 1997, ref 26; Shamblin 1999, ref 27; Marsac 2010, ref 28) ·
  • Why water splits an ASD. In the Flory–Huggins picture a hydrophobic drug interacts unfavourably with water (large χWD) while the polymer interacts favourably (small χWP); a large difference Δχ drives phase separation (the Δχ effect), and hygroscopic polymers have been seen to favour moisture-induced AAPS with other hydrophobic drugs. (Zhang 2001, ref 30; Robard 1977, ref 31; Purohit 2015, ref 14; Rumondor 2010, ref 33) ·
  • The amorphous solubility caps supersaturation. Above the amorphous solubility the drug undergoes LLPS into disordered drug-rich droplets, typically 200–500 nm, in metastable equilibrium with the solution, which stays at the amorphous solubility; for ritonavir LLPS occurs at a similar concentration whether induced by solvent shift, pH change, cooling or ASD dissolution, and the droplets can act as a reservoir that keeps membrane flux at its maximum. (Ilevbare 2013, ref 9; Raina 2014, ref 10; Taylor 2016, ref 34; Indulkar 2016, ref 35) ·····
  • Environment-sensitive probes. The pyrene I/III ratio and nile red fluorescence report the polarity around the probe and have been used to detect LLPS in solution and phase separation in ASD films. (Raina 2015, ref 18; Purohit 2015, ref 14; Purohit 2015, ref 21; Greenspan 1985, ref 22) ··
  • Loading and polymer set the release mode. Polymer type changes ASD dissolution and supersaturation; at low DL release follows polymer dissolution because there is too little drug to form a drug-rich surface, as in sulfathiazole–PVP (polymer control at about 10%, a drug-rich surface layer at about 50%) and β-carotene–PVP dispersions, and LLPS is generally seen at low DL. (Konno 2008, ref 11; Alonzo 2011, ref 12; Alonzo 2010, ref 13; Simonelli 1969, ref 36; Simonelli 1976, ref 37; Chen 2016, ref 38; Corrigan 1985, ref 39; Tachibana 1965, ref 40; Jackson 2015, ref 41) ···
  • Two candidate origins of the nanodroplets. Either the dissolved drug exceeds the amorphous solubility and undergoes LLPS in solution, or, as Harmon et al. proposed for a copovidone ASD, drug-rich nanodomains form in the matrix by AAPS, are stabilised by the polymer and are then released. (Ilevbare 2013, ref 9; Harmon 2016, ref 29) ·
  • Ritonavir dispersions split fast. Earlier work showed that 50% DL ritonavir dispersions in PVP or PVPVA undergo AAPS within 10 s of contact with bulk water, and that the Tg of amorphous ritonavir is about 45 °C. (Purohit 2015, ref 14) ·

What the paper set out to do. Find out how drug loading and polymer type affect phase transformations inside the ASD matrix and how these in turn affect dissolution, using ritonavir with PVP, PVPVA and HPMCAS, fluorescence and confocal methods beside DSC, AFM and UV, and NTA to follow the nanodroplets formed on dissolution. ···

02How they approached it

One drug, three polymers, five loadings: the state of the solid under humidity and in buffer is set beside drug and polymer release from the same kind of film, fresh and after humidity storage, at a fixed non-sink dose of 60 µg/mL. ···

RTV–PVPpolyvinylpyrrolidone K-90Hydrophilic and hygroscopic polymer with hydrogen-bond acceptors only; 10–50% DL; measured.
RTV–PVPVApolyvinylpyrrolidone vinyl acetateHydrophilic and hygroscopic, acceptors only; 10–50% DL; measured.
RTV–HPMCASMF gradeLess hygroscopic, hydrogen-bond donors and acceptors; 10–50% DL; measured.
Pure amorphous RTV and pure polymer filmsreferencesEnd points for the pyrene I/III ratio; measured.

What was done

Experiment

RTV added to buffer with or without 512 µg/mL polymer→UV extinction, pyrene fluorescence, ultracentrifugation→amorphous solubility.···

↓
Experiment

Films at 97% RH→pyrene I/III to 96 h, confocal, AFM→phase separation or not.·····

Experiment

Powders 24 h at 97% RH, then dried→DSC glass transitions.·

Experiment

Films 10 s in buffer, then dried→confocal and SEM.···

↓
Experiment

Fresh and humidity-exposed films in buffer, 25 °C→RTV by UV, polymer by colorimetry.····

Experiment

End of dissolution→free RTV, pyrene I/III in solution, NTA, PLM→LLPS or not.·······

↓
Comparison

Matrix state set beside dissolution outcome, polymer by polymer and loading by loading.··

More detail

What was done

  1. Amorphous solubility. Ritonavir in methanol (5 mg/mL) was pumped at 20 µL/min into 100 mM pH 6.8 phosphate buffer stirred at 300 rpm, and the extinction at 400 nm was logged every 10 s; the onset of scattering marks the amorphous solubility. The same was done with pyrene (0.4 ppm, I/III from emission at 360–500 nm), and solutions made cloudy at about 40 µg/mL were ultracentrifuged (35000 rpm, 30 min) and the supernatant measured. Buffer contained no polymer or 512 µg/mL PVP, PVPVA or HPMCAS; all at 25 °C. ··
  2. Dispersions. Bulk ASDs at 10, 20, 30, 40 and 50% DL were made by rotary evaporation from methanol at 45 °C, vacuum-dried at least 24 h and sieved to 150–250 µm; dissolution films were made the same way on the inner wall of 20 mL vials; spin-coated films on quartz (with 0.2% w/w pyrene or nile red) or ZnS (for AFM) served for fluorescence, confocal and AFM. ··
  3. Humidity. Films and powders were stored at 97% RH over saturated K2SO4: pyrene spectra at 0–96 h, AFM before and after 4 days, DSC after 24 h followed by 12 h of vacuum drying (modulated DSC, 2 °C/min, ±1 °C every 60 s), NTA dissolution after 4 days. The storage time before confocal imaging and before the dissolution runs of Fig. 9 is not stated. ·····
  4. Contact with buffer. 10:90 and 50:50 films were dipped in buffer for 10 s, blown dry, vacuum-dried overnight and imaged by confocal microscopy (nile red, 561 nm excitation) and by SEM. ·
  5. Dissolution. 18 mL of 100 mM pH 6.8 phosphate buffer at 25 °C was added to each film vial, giving 60 µg/mL RTV at complete release (and 540 or 60 µg/mL polymer for 10:90 or 50:50). RTV was followed in situ by UV at 240 nm minus the 400 nm baseline for about 4 h; polymer was assayed in filtered aliquots by phenol–sulfuric acid (HPMCAS, 490 nm) or potassium triiodide (PVP, PVPVA, 500 nm). ··
  6. Which solutions underwent LLPS. After 4 h, free RTV was measured in ultracentrifuged supernatants of fresh-film solutions; pyrene (0.4 ppm) was added to 1 µm-filtered solutions; NTA imaged and sized the particles; PLM checked for crystals in solution and residue. ···

Key equations

Flory–Huggins free energy of mixing (Eq. 2)
ΔGmixRT=nwlnϕw+nDlnϕD+nplnϕp+nwϕDχWD+nwϕpχWP+nDϕpχDP

The first three terms are the entropy gained by mixing water, drug and polymer; the last three are pairwise interactions. The authors use it, without numbers, to argue that water drives phase separation when it likes the polymer much more than the drug.·

Δχ effect (stated in words)
Δχ=|χWD−χWP|

The larger the gap between the water–drug and water–polymer interaction parameters, the stronger the tendency to phase separate; the authors expect a larger gap for PVP and PVPVA than for HPMCAS.·

Noyes–Whitney equation (Eq. 3, printed with the label 2)
dxdt=C(S−x)

The dissolution rate falls to zero as the concentration x approaches the solubility S of the amorphous drug; the authors use it to argue that a drug-controlled matrix cannot push the solution above the amorphous solubility, so it cannot undergo LLPS.··

Terms used on this page
  • AAPS (amorphous–amorphous phase separation): an amorphous dispersion splitting into drug-rich and polymer-rich amorphous phases, here driven by water.
  • LLPS (liquid–liquid phase separation): a solution that exceeds the amorphous solubility separating into drug-rich nanodroplets and a water-rich phase held at the amorphous solubility.
  • Amorphous solubility: the highest concentration of free drug a solution can hold before LLPS; for ritonavir about 27–28 µg/mL here.
  • Pyrene I/III: the ratio of two emission peaks of pyrene; high in polar (water- or polymer-rich) surroundings, low in hydrophobic (drug-rich) surroundings.
  • Polymer-controlled versus drug-controlled release: in the first, the dissolving polymer carries the drug out at its own rate; in the second, the drug dissolves on its own from a drug-rich matrix.
  • Congruent release: drug and polymer released at the same fractional rate.
  • Apparent concentration: UV reading of a solution containing nanodroplets, which absorb and scatter light, so it is not the free-drug concentration.
Fig. 1: Structures of ritonavir, the three polymers and the two probes
Fig. 1 · p.3 · Structures of ritonavir, the three polymers and the two probesShows. ritonavir; PVP and PVPVA with pyrrolidone acceptors only; HPMCAS with hydroxyl and succinate donors; pyrene; nile red.

03Main findings

1

Ritonavir's amorphous solubility is about 27–28 µg/mL, and the polymers do not change it

Three methods gave 26.8–28.5 µg/mL in buffer, with or without 512 µg/mL PVP, PVPVA or HPMCAS. ·

More detail

UV extinction rose sharply from 27 µg/mL upward (Table I: 27.2 µg/mL in buffer; 28.5, 27.5 and 27.5 µg/mL with PVP, PVPVA and HPMCAS); ultracentrifuged supernatants held 27.0, 27.0, 26.8 and 27.5 µg/mL; the pyrene I/III ratio changed suddenly at about 28 µg/mL (28.5 in Table I, buffer only). The standard deviation was 0.5–2 µg/mL. ·· The authors take the ultracentrifugation value as closest to equilibrium, since dynamic addition can overshoot before LLPS is detected, and call the methods "in excellent agreement"; none of the polymers had a solubility-enhancing effect at this concentration ("It is evident"). · The polymer level, 512 µg/mL, is described as the most a 10:90 ASD can release, although the fixed dose gives 540 µg/mL, and no fluorescence value with polymer is reported although the method describes one. ··

Table I: Amorphous solubility of ritonavir by three methods
Table I · p.6 · Amorphous solubility of ritonavir by three methodsShows. 26.8–28.5 µg/mL in buffer and with 512 µg/mL of each polymer.Also supports K7
2

Humidity splits the PVP and PVPVA dispersions but not the HPMCAS ones

Under 97% RH, pyrene I/III in 20–50% DL PVP and PVPVA films fell to ≈1.27–1.34 by 96 h, close to pure amorphous RTV (≈1.27–1.30); 10% DL films fell less. HPMCAS films stayed at ≈1.39–1.47. Confocal, AFM and DSC found drug-rich domains or an RTV-rich glass transition only with PVP and PVPVA. ····

Fig. 2: Pyrene I/III in films at 97% RH over 96 h
Fig. 2 · p.7 · Pyrene I/III in films at 97% RH over 96 hShows. PVP (a) and PVPVA (b) films fall toward pure ritonavir; HPMCAS films (c) stay flat.Read it as. lower I/III = pyrene in a drug-rich environment; the x-axis breaks after 6 h.Also supports K1
Fig. 3: Confocal images after 97% RH
Fig. 3 · p.8 · Confocal images after 97% RHShows. bright drug-rich domains in PVP (a, b) and PVPVA (c, d) films; uniform HPMCAS films (e, f).Also supports K1
More detail

Pyrene in the films (Fig. 2). Before exposure the I/III ratio rose with polymer content, from ≈1.50 (50:50) to ≈1.61 (PVP) or ≈1.67 (PVPVA) at 10:90, between the values of pure RTV (≈1.27–1.30) and pure polymer (PVP ≈1.83, PVPVA ≈1.75, HPMCAS ≈1.52), as expected for miscible dispersions. · At 97% RH the PVP and PVPVA ratios fell: 50:50 PVP from ≈1.50 to ≈1.30 within 1 h, the 30:70 to 50:50 PVP films to ≈1.30 by the first point after 6 h, and all 20–50% DL PVP and PVPVA films to ≈1.25–1.35 by 72–96 h. The 10:90 films changed slowly, to ≈1.35 (PVP) and ≈1.45 (PVPVA) at 96 h. HPMCAS ratios stayed within ≈1.39–1.47 at every loading for 96 h. ·· The authors read the fall as pyrene moving into drug-rich AAPS domains ("can be interpreted as follows"), with extensive AAPS by day 3 except at 10% DL and an onset "as early as 1 h", and the flat HPMCAS ratios as resistance to phase separation ("suggesting"). The 1 h onset holds for 20–50% DL, not for 10% DL. ··

Images. After 97% RH, confocal images (nile red, brighter in drug-rich regions) showed dense bright domains about 1 µm across in 10:90 PVP, interconnected domains in 50:50 PVP and PVPVA, discrete 1–3 µm domains in 10:90 PVPVA, and uniform fluorescence in both HPMCAS films; fresh films were uniform. ·· AFM of 10:90 films after 4 days showed raised domains (height scale ±150 nm, 20 µm scans; discrete domains of 5–10 µm) for PVP and PVPVA against smooth surfaces before exposure (±7.5–10 nm), while HPMCAS films showed no domains (height scale ±50 nm before, ±7.5 nm after). · AFM cannot tell which phase is drug-rich, and fluorescence and DSC say nothing about microstructure.

Glass transitions (Fig. 6). After 24 h at 97% RH and drying, every PVP and PVPVA trace showed a step at ≈47–50 °C, near the Tg of amorphous ritonavir (about 45 °C), and the PVPVA traces a second step at ≈99–108 °C; in the PVP traces a second step was distinct only at 20:80 (≈120 °C). HPMCAS dispersions showed a single step that rose from ≈63 °C (50:50) to ≈97 °C (10:90) and, by the text, did not change on exposure; all fresh dispersions had a single Tg (SI, not supplied). ·· The authors read two Tgs as moisture-induced AAPS ("consistent with"; "appears to have occurred") and the single HPMCAS Tg as miscibility "at least within the resolution" of DSC.

Fig. 5: AFM topography of 10:90 films before and after 4 days at 97% RH
Fig. 5 · p.9 · AFM topography of 10:90 films before and after 4 days at 97% RHShows. raised micron-scale domains appear on PVP (b) and PVPVA (d); HPMCAS (f) stays flat.Read it as. note the larger scan size (20 µm) and height scale (±150 nm) of b and d.Also supports K1
Fig. 6: Glass transitions after 24 h at 97% RH
Fig. 6 · p.10 · Glass transitions after 24 h at 97% RHShows. an RTV-rich step (arrows, ≈47–50 °C) in PVP (a) and PVPVA (b) dispersions; one step in HPMCAS (c).Also supports K1
3

In buffer, high-loading PVP and PVPVA films split within seconds

After 10 s in buffer, the 50% DL PVP and PVPVA films showed micron-scale phase separation, while the 10% DL films and both HPMCAS films stayed uniform. ···

Fig. 8: SEM of films after 10 s in buffer
Fig. 8 · p.12 · SEM of films after 10 s in bufferShows. rough or granular surfaces on 50:50 PVP (a) and PVPVA (c); smooth 10:90 films (b, d, f) and 50:50 HPMCAS (e).Also supports K2, K5
More detail

Confocal images after 10 s in buffer and drying showed a uniform 10:90 PVP film and a 50:50 PVP film with many dark domains of about 1–3 µm in a bright drug-rich phase; the text reports the same for PVPVA and uniform 10% and 50% DL HPMCAS films (images not shown). · SEM after the same treatment showed a rough porous network on 50:50 PVP and a granular surface on 50:50 PVPVA, and smooth surfaces on all 10:90 films and on 50:50 HPMCAS. · This matches the group's earlier finding that 50% DL ritonavir–PVP and –PVPVA dispersions phase separate within 10 s of contact with water. The results paragraph describes the SEM samples as humidity-exposed, but the caption, methods and discussion give 10 s in buffer. The 20–40% DL films were not imaged after buffer contact.

Fig. 4: Confocal images of PVP films after 10 s in buffer
Fig. 4 · p.9 · Confocal images of PVP films after 10 s in bufferShows. 10:90 uniform (a); 50:50 split into domains (b).Also supports K2
4

Only some fresh dispersions exceed the amorphous solubility and form nanodroplets

Fresh HPMCAS dispersions at every loading, PVP at 10–20% DL and PVPVA at 10% DL underwent LLPS: pyrene I/III 1.50–1.66 in solution against 1.90 in buffer, free ritonavir 27–30 µg/mL. The other PVP and PVPVA dispersions stayed at 10–25 µg/mL with I/III 1.88–1.90. ···

See also Fig. 9

Table III: Pyrene I/III in the final dissolution solutions
Table III · p.12 · Pyrene I/III in the final dissolution solutionsShows. values below the buffer's 1.90 mark LLPS: all HPMCAS, 10:90 and 20:80 PVP, 10:90 PVPVA.Also supports K3
More detail

Three read-outs agree. Pyrene I/III in the final solutions (Table III) was 1.50–1.61 for all HPMCAS dispersions, 1.63 and 1.66 for 10:90 and 20:80 PVP and 1.53 for 10:90 PVPVA, but 1.88–1.90 for the others, the buffer value being 1.90. Free ritonavir after 4 h (Table II) was 27–30 µg/mL for every HPMCAS dispersion and 28 µg/mL for 10:90 and 20:80 PVP and 10:90 PVPVA, all at the amorphous solubility; the non-LLPS dispersions held 18, 18 and 25 µg/mL (PVP 50:50 to 30:70) and 10, 12, 16 and 22 µg/mL (PVPVA 50:50 to 20:80). NTA found nanodroplets in the same LLPS group, with mean sizes of 200 nm (PVPVA), 250 nm (HPMCAS) and 315 nm (PVP) for fresh 10:90 films. ·· The authors read the I/III decrease as pyrene entering ritonavir-rich nanodroplets ("indicates") and assume no LLPS without a significant decrease.

Dissolution profiles (Fig. 9). Apparent concentrations of LLPS-forming films spiked within minutes: ≈130 µg/mL (line maximum; 10:90 PVP), ≈80 (20:80 PVP), ≈116 (10:90 PVPVA), and ≈119, ≈67 and ≈49 µg/mL for 10:90, 20:80 and 30:70 HPMCAS; 40:60 and 50:50 HPMCAS stayed at ≈30–33 µg/mL. Non-LLPS PVP and PVPVA films rose slowly to ≈9–26 µg/mL at 240 min. ·· The spikes decayed (10:90 PVP to ≈17, 10:90 HPMCAS to ≈21 µg/mL at 240 min) while free drug stayed at about 28 µg/mL; no crystals were found by PLM, and the authors ascribe the fall to nanodroplets scattering light and coalescing, not to crystallization. ····

Table II: Free ritonavir after 4 h (fresh films)
Table II · p.12 · Free ritonavir after 4 h (fresh films)Shows. 27–30 µg/mL for LLPS-forming dispersions; 10–25 µg/mL for the others.Also supports K3
Fig. 7: NTA images of solutions after dissolution
Fig. 7 · p.11 · NTA images of solutions after dissolutionShows. many scattering particles from fresh PVP, PVPVA and HPMCAS films and from exposed HPMCAS; almost none from exposed PVP (b) and PVPVA (d).Also supports F6, K3
5

The polymer dissolves fast; the drug keeps pace only where LLPS occurs

From 10:90 films polymer and ritonavir both came out within minutes (ritonavir ≈83–116 µg/mL at about 5 min). From 50:50 films the polymer still dissolved, but ritonavir reached only ≈18 µg/mL with PVP and ≈9 µg/mL with PVPVA; with HPMCAS it rose with the polymer to ≈33 µg/mL. ···

Fig. 10: Drug and polymer release from 10:90 and 50:50 films
Fig. 10 · p.14 · Drug and polymer release from 10:90 and 50:50 filmsShows. polymer dissolves early in every case; ritonavir follows from 10:90 films and from 50:50 HPMCAS, but lags from 50:50 PVP and PVPVA.Read it as. polymer on the right axis; 540 and 60 µg/mL are the polymer amounts at full release.Also supports K4
More detail

For 10:90 films, polymer reached ≈500 of 540 µg/mL PVP by 10 min, ≈565 µg/mL PVPVA and ≈550 µg/mL HPMCAS by about 5 min, and ritonavir rose at the same time to ≈83 (PVP; line maximum ≈130), ≈116 (PVPVA) and ≈113 µg/mL (HPMCAS). ····· For 50:50 films, PVP reached ≈57 of 60 µg/mL within 5 min and HPMCAS ≈53 by 20 min, but PVPVA only ≈22 at 5 min, ≈45 at 60 min and ≈65 near 120 min; ritonavir reached ≈18 (PVP) and ≈9 µg/mL (PVPVA) by 240 min, but ≈32–34 µg/mL within 5 min with HPMCAS. ····· The authors read this as congruent release where colloids form and drug lagging far behind the polymer where they do not, and state that the polymer dissolves "almost completely in less than 10 min" in all cases; 50:50 PVPVA took about 2 h. ··· Polymer release was shown only for fresh 10:90 and 50:50 films; for the other loadings the text states that all polymer dissolved early. ··

6

Humidity storage removes LLPS from PVP and PVPVA dispersions but not from HPMCAS

After 97% RH, 10:90 PVP and PVPVA films no longer spiked and crept to ≈30 and ≈25 µg/mL, and NTA found no nanodroplets from any PVP or PVPVA film. HPMCAS films still peaked at ≈90–131 µg/mL at 10–30% DL and still formed nanodroplets. ·····

See also Fig. 7

Fig. 9: Dissolution of fresh and humidity-exposed films, 10–50% DL
Fig. 9 · p.13 · Dissolution of fresh and humidity-exposed films, 10–50% DLShows. spikes above the amorphous solubility (dashed line) for fresh low-loading PVP and PVPVA and for HPMCAS; the PVP and PVPVA spikes vanish after humidity (b, d), the HPMCAS ones remain (f).Also supports F4, K3
More detail

With PVP, humidity storage slowed release most at 10% and 20% DL: the 10:90 film reached ≈25 µg/mL after ≈25 min and ≈30 at 240 min instead of a ≈130 µg/mL spike, and all exposed PVP films stayed at or below the amorphous solubility (≈14–30 µg/mL at 240 min); higher loadings changed little. · With PVPVA only the 10% DL profile changed, from a ≈116 µg/mL spike to ≈25–26 µg/mL; the others stayed at ≈10–21 µg/mL. · HPMCAS films after exposure still spiked (≈131, ≈124 and ≈90 µg/mL for 10:90, 20:80 and 30:70) and stayed higher at 240 min (≈65, ≈45, ≈42 µg/mL) than fresh films; the authors state that exposure "did not impact" the dissolution kinetics, which holds for the fast rise and the LLPS but not for the height of the profiles. ·· NTA showed no nanodroplets from exposed PVP or PVPVA films and nanodroplets from all exposed HPMCAS films. · The authors conclude, "very clearly", that a phase-separated matrix dissolves more slowly and no longer reaches LLPS. How long the dissolution films had been stored at 97% RH is not stated.

04Further observations

  • No crystals formed in any solution or residue during the tests.
  • The fall in apparent concentration after the spike is ascribed to nanodroplets scattering light and coalescing.
  • Mean nanodroplet size: 200 nm (PVPVA), 250 nm (HPMCAS), 315 nm (PVP).
  • Powders behaved like films, with different rates. ·
  • Humidity-exposed HPMCAS films gave higher apparent concentrations than fresh ones. ·
More detail
  • No crystallization. Polarized light microscopy found no crystals in solution or in the undissolved ASD at the end of any dissolution run, so the authors attribute the decay of the apparent concentration after the spike to nanodroplets that absorb and scatter UV light and aggregate or coalesce over time (UV at 240 nm, corrected at 400 nm), while the free drug stays at about 28 µg/mL. ···
  • Nanodroplet size. Fresh 10:90 films gave mean sizes of 200 nm (PVPVA), 250 nm (HPMCAS) and 315 nm (PVP), an order of magnitude below the 1–10 µm domains seen in phase-separated films. ···
  • Powders. Powdered dispersions (150–250 µm, 100 mL buffer) showed LLPS for the same combinations as films; data are not shown and rate differences are attributed to surface area. ··
  • HPMCAS after humidity. Exposed HPMCAS films reached higher apparent peaks than fresh films at 20:80 (≈124 against ≈67 µg/mL) and 30:70 (≈90 against ≈49 µg/mL) and stayed higher at 240 min; the 50:50 film plateaued at ≈33–34 µg/mL in both states. ·
  • Highest-loading HPMCAS. The 50:50 HPMCAS film gave an apparent plateau of ≈33 µg/mL, free ritonavir 27 µg/mL and pyrene I/III 1.61, the authors' evidence that even 50% DL HPMCAS reaches LLPS. ···

05How the authors connect the findings

1Water entering a dispersion of a hydrophobic drug makes the polymer and water a co-solvent in which the drug's miscibility is exceeded, so the matrix splits (the Δχ effect). ·
↓
2PVP and PVPVA, more hygroscopic and without hydrogen-bond donors, are expected to split more readily than HPMCAS. ·
↓
3On contact with buffer, dissolution of the matrix races against its phase separation.
↓
Matrix stays miscible(all HPMCAS; fresh PVP and PVPVA at low loading)↓the dissolving polymer carries the drug out congruently↓concentration exceeds the amorphous solubility↓LLPS forms nanodroplets.···
Matrix has split(PVP and PVPVA at high loading within seconds; any loading after humidity)↓the polymer dissolves away and leaves amorphous drug↓drug-controlled release stops at the amorphous solubility↓no nanodroplets.···
What sets the switch point. How fast the matrix phase separates compared with how fast it dissolves, set by drug loading and by the polymer's affinity for water ("appears to depend"). ·
Conclusion drawn. The nanodroplets "likely" come from LLPS in solution, not from matrix domains, and dispersions should be designed to resist AAPS. ··
Fig. 11: Possible phase transformations of a dissolving ASD
Fig. 11 · p.17 · Possible phase transformations of a dissolving ASDShows. miscible or phase-separated matrix, LLPS or not in solution, and crystallization routes.
More detail
  1. Sorbed water turns the binary dispersion into a ternary system. In Flory–Huggins terms water likes the polymer (small χWP) and dislikes the hydrophobic drug (large χWD); when the difference Δχ is large the system phase separates. The authors describe AAPS as "a classic case of solvent-induced immiscibility": the drug, dissolved in the polymer, loses miscibility as water and polymer become a co-solvent, provided the matrix is mobile enough. ···
  2. PVP and PVPVA are more hydrophilic and hygroscopic than HPMCAS and carry only hydrogen-bond acceptors, whereas HPMCAS has donors and acceptors that can interact more variously with ritonavir; the authors expect ("can be expected", "are expected") a larger Δχ and so more AAPS for PVP and PVPVA, which the humidity data then show. ····
  3. During dissolution the outcome "appears to depend" on which is faster: dissolution of the miscible matrix, or its phase separation on contact with water.

Dissolution wins. The polymer dissolves and carries the molecularly dispersed drug with it at the same rate, as for low-loading dispersions in earlier work; the solution passes the amorphous solubility and the excess drug separates as amorphous nanodroplets. HPMCAS dispersions resist AAPS, so this happens even at 50% DL ("can explain"). ····

Phase separation wins. At 50% DL with PVP or PVPVA the matrix splits within seconds of water contact; after humidity storage it is split before dissolution starts. The polymer then dissolves quickly and leaves a matrix of mainly amorphous ritonavir, release becomes drug-controlled, and by Noyes–Whitney the dissolution rate falls to zero at the amorphous solubility, so the solution cannot undergo LLPS ("We attribute this to"; "can be readily explained"). ····

What sets the switch point. The relative rates of matrix dissolution and matrix phase separation; drug loading and the polymer's hygroscopicity and hydrogen bonding set how fast the matrix splits. Neither rate was measured during dissolution. ··

Conclusion drawn. "we find no evidence" that the colloids come from matrix phase separation: low-loading films show no domains after 10 s in buffer, and matrix domains are micron-sized while the droplets are an order of magnitude smaller. Nanodroplet formation "is likely caused by" rapid dissolution of miscible dispersions followed by LLPS, and formulators should design dispersions that resist AAPS and dissolve under polymer control. ··

06What it means for formulation

Stated by the authors
  • Design ASDs that resist AAPS and dissolve under polymer control.
  • A dispersion that has phase separated, for example after humid storage, dissolves more slowly and no longer reaches LLPS.
AI reading, not stated in the paper
  • For a hydrophobic drug such as ritonavir in PVP or PVPVA, humid storage threatens release, not only physical stability.
  • The polymer sets how much drug can be loaded before release fails: here 10–20% DL with PVP, 10% with PVPVA, at least 50% with HPMCAS.
More detail
Stated by the authors
  • To achieve superior dissolution, formulators should design dispersions that are resistant to AAPS and show polymer-controlled dissolution ("based on our observations").
  • Matrix phase separation, here induced by high humidity, slows dissolution and removes the nanodroplets; dispersions that resist it dissolve faster and reach higher supersaturation.
  • Understanding how formulation components, drug loading and water govern phase behaviour "will enable" rational design.
AI reading, not stated in the paper
  • For PVP- and PVPVA-based dispersions of a hydrophobic drug, moisture protection matters for performance as well as for crystallization: the 10:90 dispersions lost their nanodroplets after humid storage without crystallizing.
  • A brief water-contact test (seconds in buffer, then imaging) separated good from poor performers here and could serve as a quick screen of polymer and loading.
  • The loading threshold seen here, between 20% and 30% DL for PVP and between 10% and 20% for PVPVA, is the behaviour later work calls a limit of congruency; this paper does not use that term.
  • All tests were at 25 °C in phosphate buffer; the ranking of the polymers at 37 °C or in biorelevant media is not shown here.

07Open questions

Raised by the authors
  • How formulation components, drug loading and water together set the phase behaviour, which they see as the basis for rational design.
Not covered by this paper (AI reading)
  • The rates of dissolution and of phase separation were not measured during dissolution.
  • Nanoscale domains below about 300 nm in low-loading films were not excluded.
More detail
Raised by the authors
  • The conclusions call for understanding the relationships between formulation components, drug loading, water and ASD phase behaviour as the basis for rational design.
Not covered by this paper (AI reading)
  • The race between dissolution and phase separation is inferred from end points; neither rate was measured on dissolving films.
  • Low-loading films were imaged after 10 s and drying at a confocal resolution of about 300 nm, comparable with the 200–315 nm droplets, so a matrix origin of the nanodroplets is not excluded at that scale. ·
  • Polymer release was shown only for fresh 10:90 and 50:50 films; the 20–40% DL films and all humidity-exposed films were not followed.
  • Water uptake of the films, drug–polymer hydrogen bonding and interaction parameters, on which the HPMCAS explanation rests, were not measured.
  • One drug, 25 °C, one buffer; replicate numbers and the storage time before the dissolution runs are not stated. ·

08How solid

AI assessment, not a statement made in the paper
Moderate

Humidity-induced phase separation is shown by four independent methods, and the LLPS classification by three read-outs that agree. ······ The mechanism linking the two, and the origin of the nanodroplets, are inferred rather than measured, and several statements go beyond the data shown. ····

More detail
What holds
  • Pyrene fluorescence, confocal imaging, AFM and DSC agree that PVP and PVPVA dispersions phase separate at 97% RH and HPMCAS dispersions do not. ···
  • Pyrene in solution, free drug after ultracentrifugation and NTA identify the same LLPS-forming dispersions. ··
  • The full design (three polymers, five loadings, fresh and humidity-exposed) gives a consistent pattern: LLPS appears only where the matrix stays mixed. ··
  • Amorphous solubility agrees across three methods within 2 µg/mL.
What weakens it
  • The race between dissolution and phase separation is a reading of end points; the rates were not measured.
  • The case against a matrix origin of the nanodroplets rests on imaging at about the droplets' size.
  • Congruent release is shown only at 10% DL (and initially at 50% DL HPMCAS).
  • Some statements are stronger than the data: AAPS "as early as 1 h" does not hold for 10% DL, polymer dissolution "in less than 10 min" not for 50:50 PVPVA, "no impact" of humidity not for the HPMCAS profiles, two Tgs not for most PVP traces. ···
  • Key conditions are unstated or inconsistent: storage time before dissolution and confocal imaging, the state of the Table III solutions, the exposure used for SEM. ··
  • The explanation for HPMCAS (hygroscopicity, hydrogen bonding, Δχ) was not tested.

09Figure guide

Every figure and table of the paper, what it is there for, and what to check on the original. Key figures are shown with the story.

FigureWhat it does in the paperSupportsCheck (AI note)
Fig. 1 (p.3)key figureDefines ritonavir, the three polymers and the two fluorescent probes.·····0.2Pyrene drawn with two saturated ring positions.
Table I (p.6)key figureSets the amorphous solubility at 26.8–28.5 µg/mL and shows no polymer effect.F1, K7Polymer at 512, not 540 µg/mL; fluorescence only in buffer.·
Fig. 2 (p.7)key figureTracks phase separation in films at 97% RH by pyrene I/III.F2, K110% DL films change slowly; legend symbols swap between panels.·
Fig. 3 (p.8)key figureShows drug-rich domains after humidity in PVP and PVPVA films, none in HPMCAS.F2, K1Storage time not stated.
Fig. 4 (p.9)key figureShows that 50:50 PVP films split within 10 s in buffer and 10:90 films do not.F3, K2
Fig. 5 (p.9)key figureShows micron-scale domains on PVP and PVPVA films after 4 days at 97% RH.F2, K1
Fig. 6 (p.10)key figureShows an RTV-rich Tg after humidity in PVP and PVPVA dispersions, one Tg in HPMCAS.F2, K1Second Tg distinct in only one PVP trace.
Fig. 7 (p.11)key figureShows which dissolution solutions contain nanodroplets, fresh and after humidity.F4, F6, K3Loading of the images not stated.
Fig. 8 (p.12)key figureShows surface phase separation of 50:50 PVP and PVPVA films after 10 s in buffer.F3, K2, K5Results text names 97% RH instead of 10 s in buffer.
Table II (p.12)key figureGives free ritonavir after 4 h: at the amorphous solubility only for LLPS-forming dispersions.F4, K3
Table III (p.12)key figureIdentifies LLPS by pyrene I/III in the final solutions.F4, K3Fresh or exposed films not stated.
Fig. 9 (p.13)key figureThe central comparison: dissolution of all 30 film types, fresh and after humidity.··F6, F4, K3Storage time not stated; HPMCAS profiles change after humidity.·
Fig. 10 (p.14)key figureCompares drug and polymer release for 10:90 and 50:50 films.··F5, K450:50 PVPVA dissolves over about 2 h; 10:90 PVPVA exceeds the theoretical amount.·
Fig. 11 (p.17)key figureSchematic of matrix and solution phase transformations during ASD dissolution.0.5A schematic, not data.