Benefits and Limitations of Using Cyclodextrins in Drug Formulations
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1 Benefits and Limitations of Using Cyclodextrins in Drug Formulations István Puskás, Milo Malanga CycloLab Ltd., Hungary Session 1-2: Enhancing Bioavailability with New Technologies and Strategies 1
2 Outline Cyclodextrins (CDs) as effective solubilizers in drug formulations Cyclodextrins facilitating enhancement of pharmacokinetic properties Cyclodextrins for targeted drug delivery Application in colloidal structures 2
3 Cyclodextrins Cyclic glucopyranose oligosaccharides 6-8 a-d-glucose units (a, b, g-cyclodextrin) 3
4 Cyclodextrins Lipophylic region Doughnut or truncated cone shape molecules Inclusion complexation Molecular self-assemby Hydrophilic region 4
5 Cyclodextrin derivatives R = H, or -CH 3 -CH 2 CH(OH)CH 3 -CH 2 CH 2 CH 2 CH 2 SO 3 Na 5
6 CDs suitably used in pharmaceuticals Parent Native Unsubstituted a-cd (Alfadex) EP, USP Derivatives Substituted 2-hydroxypropyl b-cd (HP-b-CD) EP, USP 2-hydroxypropyl g-cd b-cd (Betadex) EP, USP g-cd USP, JPC sulfobutylether b-cd (SBE-b-CD) USP random metylated b-cd (RM-b-CD) (rare: nasal/ocular) 6
7 Chemistry Nobel Prize 2016: Sir Fraser Stoddart (UK) "för design och syntes av molekylära maskiner" Switchable rotaxanes may act as drug-release nanovalves in an attempt to develop controllable drug delivery systems for use in the fight against cancer. 7
8 Cyclodextrin complex formation CD + G CD G 8
9 The association with cyclodextrin may be versatile 9
10 Chemical stability increases: - Dihydro prostaglandin E1 hn, O 2, OH -, H + - Doxorubicin (g-cd), daunorubicin (methyl-b-cd) - Acetylsalicylic acid (b-cd) - O 6 -Benzylguanine (SBE-b-CD) Chemical stabiliy decreases: Penicillin derivatives are sensitized in the presence of cyclodextrins 10
11 Effect of CDs on the bioavailability of drug substances Class III Highly soluble Poorly permeable Class I Highly soluble Highly permeable low Class IV Poorly soluble Poorly permeable Class II Poorly soluble Highly permeable low high Permeability Amidon et al 1995, Pharm. Res. 12: ; T. Loftsson 2002, J.Incl.Phenom. 44:
12 Consequences of CD complexation Cyclodextrins may increase: Wetting, dissolution rate Drug solubility Absorbed quantity Cyclodextrins may decrease: Taste Irritation Drug stability Smell Side effects 12
13 CDs suitably used in pharmaceuticals European Medicinal Agency EMA/CHMP/333892/2013, Committee for Human Medicinal Products (CHMP)Background review for cyclodextrins used as excipients ~49 pharma products on the market containing CD 13
14 Solubility enhancement of drugs using 10 m/m% SBE-b-CD vs. purified water Piroxicam Carbamazipine Amiodarone Voriconazole Delafloxacin Ziprasidone.HCl hydrate Aripiprazole Posaconazole ph 6 Posaconazole ph 3 20 x 36 x 50 x 85 x 340 x 470 x 3350 x 20 x 120 x Aqueous solubilities: Pubmed database ( solubility in SBECD solutions: Cyclolab results 14
15 Succesful formulations using SBE-b-CD for dissolving APIs of poor solubility 15 15
16 SBE-b-CD in veterinary formulation Canine Anti-Nausea 16
17 Purpose of using CDs other than solubilizing Fast onset Taste masking Thiomersal free, reduced irritation 17
18 Purpose of using CDs other than solubilizing Ulgut (benexate): masking bitter taste Chemical stabilization Masking bitter taste 18 18
19 Sugammadex: Revolution in anaesthesiology! 19
20 Sugammadex: Revolution in anaesthesiology! The muscle relaxant is bound irreversibly 20
21 Folate appended cyclodextrins a, b or g Targeting moiety Drug delivery or active moiety R. Onodera, K. Motoyama, A. Okamatsu, T. Higashi, H. Arima, Scientific Reports, 2013, 3, J. Szemán, K. Csabai, E. Varga, M. Malanga, K. Ludányi, L. Szente: HPLC Analysis of Folate Appended Cyclodextrins, HPLC 2017, Prague, June,
22 Cyclodextrins in colloidal drug delivery: Liposomes in combination with host-guest chemistry Cyclodextrin Polymer I. Puskás, F. Csempesz: Colloids and Surfaces B: Biointerfaces 58(2), (2007) 22
23 Thermosensitive liquid crystalline drug/cyclodextrin assemblies: Amiodarone / gamma-cd construct DSC Heat flow (W/g) 2 1,5 1 0,5 0 T m T / Celsius endo Room temperature: Liquid crystal Elevated temperature: Sol 23
24 g-cd / surfactant / hyaluronic acid supra-colloidal construct Szente, L., Puskás, I., Csabai, K., Fenyvesi, É.: Chemistry an Asian Journal, 9(5), (2014) 24
25 In vitro disassembly of non-covalent polymer matrix containing fluorescent bovine serum albumin purified water in isotonic 0.9 % NaCl time 0 24 hours 36 hours 48 hours 25
26 Supra-colloidal assembly for sustained release of antiretroviral drugs NH 2 O N H 3 C NH HO O N O HO O N O S lamivudine N 3 zidovudine Polylysine Hyaluronic acid SBE-b-CD B. Song, I. Puskás, L. Szente, J. E. K. Hildreth: J. Pharm. Sci. 105(9), 2760,
27 Conclusions Major benefits of using CDs in drug formulations: - Enhancing bioavailability - Succesful injectable formulations of poorly soluble drugs - Stabilization (physical / chemical) Limitations: - Administration routes of some CDs are limited - Supergeneric strategy was not a success Opportunities: - CD complexes of special tunable colloidal forms - Designed (smart) CD-derivatives for drug delivery 27
28 Acknowledgements Lajos Szente (Cyclolab Ltd) Éva Fenyvesi (Cyclolab Ltd) Zsuzsa Simon (Cyclolab Ltd) This work was sponsored by FP7-PEOPLE-ITN
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