Table 3.
An overview of ternary drug/CD complexes prepared by grinding using high-energy vibrational mills.
| Drug | CD/Ternary Compound 1 | Drug/CD/Ternary Compound Ratio 2 | Grinding Conditions | Properties of the Obtained Product | Reference |
|---|---|---|---|---|---|
| Dehydroepiandrosterone (mp 150.9 °C) | αCD + glycine | 1:1:2 or 1:2:3 | 60 min at 24 Hz, ambient conditions | Partially crystalline product at 1:1:2 and amorphous at 1:2:3 molar ratio. Superior performance of 1:2:3 complex confirmed in vivo | [94] |
| Econazol (mp 89.0 °C) | αCD + malic acid | 1:1:1 | 60 min at 24 Hz ambient conditions, batch size 1 g | Partially crystalline ternary product prepared by GR; FD was amorphous with superior dissolution properties | [75] |
| Econazol nitrate (mp 123.12 °C) | SBEβCD + citric acid | 1:1:1 | 60 min at 24 Hz and ambient conditions | Amorphous product with superior dissolution profile, without supersaturation phenomenon, as instead observed for binary GR complex | [80] |
| Ketoprofen (mp 96.5 °C) | βCD or RAMEB + EPC | 20:76:4 (w/w) | 15 or 30 min at 24 Hz and ambient conditions | Partially crystalline ternary complexes prepared by GR, amorphous when prepared by MWI that showed superior dissolution profile | [33] |
| Naproxen (155.9 °C) | HPβCD + L-arginine | 1:1:1 | 60 min at 24 Hz and ambient conditions; batch size 500 mg | Enhanced dissolution of ternary complex prepared by GR, further dissolution increase of ternary complex prepared by COE | [62] |
| Naproxen (155.9 °C) | HPβCD + PVP | 1:1 + 15% (w/w) | 60 min at 24 Hz and ambient conditions | Amorphous binary and ternary GR systems; ternary showed 100% higher drug dissolution efficiency than the binary ones | [78] |
| Oxaprozin (mp 161.3 °C) | RAMEB + bile acids/salts + chitosan | 1:1:1 + 0.0625% (w/w) | 30 min at 24 Hz and ambient conditions | Amorphous ternary and quaternary products with enhanced dissolution and permeability. GR products showed superior performance than those prepared by COE and SH | [23] |
| Oxaprozin (mp 161.3 °C) | RAMEB + L-arginin | 1:1:1 | 30 min at 24 Hz and ambient conditions | Amorphous products both in binary and ternary complexes; ternary with 10 times higher relative dissolution rate than binary complexes | [95] |
| Praziquantel (mp 142.28 °C) | HPβCD or RAMEB + malic acid | 1:1:1 | 10 mL SS jars containing two 7 mm SS balls for 30 min at 25 HZ and ambient conditions; batch size 200 mg | Amorphous ternary complexes with solubility lower than corresponding binary ones. Ternary complex formation led to pronounced chemical degradation of the drug | [36] |
1 The full name of CDs is given in the Introduction; 2 molar ratio if not otherwise stated; mp, melting point; SS, stainless steel.