Lipid based DDS for oral delivery of macromolecule JULIEN MEISSONNIER DIRECTOR, R&D PLATFORM
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1 Lipid based DDS for oral delivery of macromolecule JULIEN MEISSONNIER DIRECTOR, R&D PLATFORM
2 Plan Challenges Considerations for oral forms development Permeations enhancers Oral delivery of macromolecules an example
3 Current challenge Most pharmaceutical macromolecules are formulated as solution or suspensions and delivered by invasive route (e.g. IM, IV, SC )
4 Consideration for oral forms development Requirement for high potency and wide therapeutic windows (low and variable exposure) Selection of a predictive animal model Anticipation of local safety issues associated to the drug delivery system
5 Factors influencing oral absorption: Molecular size and flexibility versus charge and molecular weight 26.6 kda Random coil secondary structure: R H =36 ±1 Å 99% COOH side chains α-helix secondary structure: R H =30 ±1 Å 33% COOH side chains The permeantgeometry, structural rigidity are more important than its charge, Mw and hydrodynamic radius Data from Salamat-Miller N et al., Pharmaceutical Research, 2005, 22(2):
6 Factors influencing oral absorption: Lipophilicity Improved permeability of lipophilicpeptides is potentially related to displacement of paracellular to transcellular route Data from Knipp GT et al., Pharmaceutical Research, 1997, 14:
7 There are numerous barriers to overcome Proteolytic enzymes in the stomach and intestine Acidic conditions in the stomach Mucus Layer Gel Barrier Limited and random transcellular pathway Tight Junction fence and gate function
8 Paracellular Transport Tight Junctions are formed by the combination of integral TJ proteins, TJ plaque proteins and cytosolic nuclear proteins
9 Permeation Enhancers Catalent Confidential: Internal Use Only.
10 Permeation Enhancers Enhancer Mechanism Company/Tech Product(s) SNAC, 5-CNAC Non covalent complexation. Increase lipophilicity. Transcellular. Emisphere (Eligen ) CT (OP, OA) PTH Heparin Bile salts Non covalent complexation. Increase lipophilicity. Transcellular. Unigene - CT (piii), PTH Octreotide Medium chain fatty acids salts Tight junction modulators. Paracellular Merrion(GIPET ) Chiasma (TPE ) ISIS Zolendronicacid, Insulin, GLP-1 Oligonucleotides EDTA/EGTA Calcium chelation. Paracellular. Oramed Exenatide, Insulin Alkylglucoside Weak enhancer. Tight junction activation. Aegis(Intravail ) Octreotide, GLP- 1 Hydrophilic aromatic alcohols Weak enhancers. Proxima Concepts (Axess ) Insulin, CT Ionic Surfactants Partition in lipid layer at high concentrations. Trancellular. - - Wide variety of permeation enhancers and enhancement mechanisms
11 Bile Salts Derivative Bile salts increase membrane fluidity Chenodeoxycholate(CDCA) has a higher effect compared to Urodeoxycholate(UDCA) Bile salts improve absorption potentially through affecting membrane fluidity (PL solubilization) Data from Fricker G et al., Br J Pharmacology, 1996, 117(1):
12 N-Acetylated Amino Acids SNAC (sodium N-[8-(2- hydroxybenzoyl)amino]caprylate) Non covalent complexation GLP-1, PTH, sct, Heparin evaluated 5-CNAC evaluated for sct (failed OA) and PTH (failed several end points) Permeability enhancement through trancellular route Data from Hess S et al., Eur J of Pharm Sci, 2005, 25:
13 Sodium Caprate Sodium caprate cause a redistribution of TJ proteins from lipid rafts Data from Sugibayashi K et al., Eur J of Pharm Sci, 2009, 36:
14 Sodium Caprate Sodium capratecause claudinand occludinto translocateas granular structures in the cytoplasm Data from Kurasawa M et al., Biochemical and Biophysical Research Communications, 2009, 381:
15 Paracellular permeation enhancers: Sodium Caprate Data from Maher S et al., Advanced Drug Delivery Review, 2009, 61:
16 Sodium Caprate Cause dilatation of TJ Affect F-actinreorganization by mobilizing intracellular calcium Displacement of claudin and occludin Deterioration of TJ strands Permeation effect modulated in sequence through PLC, Calmodulin and MLKC activation Reduction in intracellular ATP Sodium caprateprovides permeability enhancement through multiple actions on the TJ
17 Oral delivery of macromolecules an example Catalent Confidential: Internal Use Only.
18 The Drug Substance Mw > 2,500 Da Freely soluble in water Limited molecular flexibility Strongly negatively charged Poor permeability Not subject to enzymatic degradation sc injection shows complete absorption Catalent Pharma Solutions data
19 Lipid-based Drug Delivery Systems Dispersion Digestion Consider the fate of lipid based DDS while investigating their potential Fig from Porter CJH et al., Nature Reviews Drug Discovery, 2007, 6:
20 In-vitro digestion tests Digestion media : ph 6.5 buffer, 1.5 mmpl / 7.5 mmbs Pancreatic lipase solution: 4,000 TBU/mL Formulation concentration: 10 to 20 mg/ml Catalent Pharma Solutions data
21 Direct Intra Duodenal Injection Fasted female WistarHan rats ( gr) 2 mg/kg bwand 500 µl WFI flexible catheter inserted upper the bile duct upper part of the duodenum closed Catalent Pharma Solutions data
22 Formulation screening Formulation # API MCT MDC Surfactant (transcellular) Hydrophilic solvent Percentage digested (%) mmol C 10 release / g nm Bioavailability (%) 27 ± 23 0 ± 0 31 ± 19 2 ± 2 Sodium caprate 50 mg/kg bw provides a bioavailability of 23 % ± 9 Lipid digestion products provide enhancement Catalent Pharma Solutions data
23 Formulation screening (ct d) 2 Plasma Concentration (µg/ml) 1,5 1 0,5 Sodium Salt Organic Salt 0 0 0,5 1 1,5 2 2,5 Time (h) Salt conversion to increase lipophilicity& transcellular uptake failed Catalent Pharma Solutions data
24 Formulation screening (ct d) Worked to improve formulation digestibility Lipophilic cluster covalently bound to the API Formulation # A B C D API Native Native Native Lipophilic cluster added Formulation approach Initial Lipolysis improvement Increase C 10 release Lipolysis improvement Bioavailability (%) 31 ± ± ± ± 18 Sodium caprate 50 mg/kg bw provides a bioavailability of 23 % ± 9 Chemical compatibility Chemical modification not opted. Formulation B selected for further animal studies Catalent Pharma Solutions data
25 Animal Studies pkstudy in dogs (n=6) fasted state Formulation F (%) versus sc injection sc injection - API solution 16 ± 4 API + Na caprate 50 mg/kg bw 20 ± 13 Formulation B SGC 10 ± 5 Formulation B EC SGC 39 ± 12 Enteric coating required to materialize the benefits Catalent Pharma Solutions data
26 Formulation development Enteric coating achieved using IMA 10 L coater Typical enteric coating formulation ranges Ingredient Function Composition (% w/w) Methacrylic Acid Ethyl Acrylate Copolymer(1:1) 30 % Dispersion Coating material Macrogol 400 / Triethyl Citrate Plasticizer Talc / Glyceryl Monostearate Lubricant Simeticone Emulsion Anti-foaming agent Purified water Solvent Catalent Pharma Solutions data
27 Formulation development Coating homogeneity confirmed by MEB Catalent Pharma Solutions data
28 Formulation development All formulations comply with EP disintegration test specifications Catalent Pharma Solutions data
29 Formulation development Capsule content marked with an iodine derivative Capsule administered to anesthetized beagle dogs Parallel blood sampling and imaging Catalent Pharma Solutions data
30 Formulation development time 1,00 (µg/ml plasma) 0,75 0,50 0,25 0, Time (h) Capsule batches retained in the stomach show limited oral absorption Catalent Pharma Solutions data
31 Formulation development time (µg/ml plasma) 2,00 1,75 1,50 1,25 1,00 0,75 0,50 0,25 0, Time (h) Capsules batches reaching the duodenum deliver proper absorption Catalent Pharma Solutions data
32 Summary Oral delivery can be achieved through transcellularand/or paracellular route enhancement Several approaches are progressing to humans When chemical modification of the API is not an option, lipid permeation enhancers are the major and safest option Catalent has established basis of applying Softgellipid DDS for oral delivery of macromolecules and will validate those in humans
33 more products. better treatments. reliably supplied. CATALENT PHARMA SOLUTIONS 14 SCHOOLHOUSE ROAD, SOMERSET, NJ Call: Visit:
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