Parenteral formulation of an antileishmanial drug candidate - Tackling poor solubility, chemical instability, and polymorphism

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 85, Issue 3 PART A, 2013, Pages 511-520

  Kupetz, Eva ^a   Preu, Lutz ^a   Kunick, Conrad ^a   Bunjes, Heike ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Cubic phase nanoparticles; Formulation screening; Lipid nanocarriers; Liposomes; Mixed micelles; Passive loading; Photoisomerization; Supercooled smectic cholesterol myristate nanoparticles; Triglyceride emulsion

Indexed keywords

ANTILEISHMANIAL AGENT; BILE SALT; KUREI 300; LIPOSOME; NANOCARRIER; NANOPARTICLE; NITROGEN; PHOSPHATIDYLCHOLINE; TRIACYLGLYCEROL; UNCLASSIFIED DRUG;

ARTICLE; DECOMPOSITION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG FORMULATION; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; EMULSION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; ISOMERIZATION; LEISHMANIA DONOVANI; LIPOPHILICITY; MICELLE; NONHUMAN; PARTICLE SIZE; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; ULTRAVIOLET SPECTROSCOPY; WETTABILITY; X RAY POWDER DIFFRACTION;

CUBIC PHASE NANOPARTICLES; FORMULATION SCREENING; LIPID NANOCARRIERS; LIPOSOMES; MIXED MICELLES; PASSIVE LOADING; PHOTOISOMERIZATION; SUPERCOOLED SMECTIC CHOLESTEROL MYRISTATE NANOPARTICLES; TRIGLYCERIDE EMULSION;

ANTIPROTOZOAL AGENTS; BENZAZEPINES; CHEMISTRY, PHARMACEUTICAL; CHOLESTEROL ESTERS; DRUG CARRIERS; DRUG COMPOUNDING; DRUG STABILITY; DRUG STORAGE; EMULSIONS; INDOLES; INJECTIONS; LIPIDS; LIPOSOMES; MICELLES; NANOPARTICLES; SOLUBILITY; TRIGLYCERIDES;

EID: 84888367043     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2013.02.001     Document Type: Article

References (31)

1. World Health Organization, < http://www.who.int/leishmaniasis/burden/ magnitude/burden-magnitude/en/index.html > (accessed 2012).
2. C. Reichwald, O. Shimony, U. Dunkel, N. Sacerdoti-Sierra, C.L. Jaffe, and C. Kunick 2-(3-Aryl-3-oxopropen-1-yl)-9-tert-butyl-paullones: a new antileishmanial chemotype J. Med. Chem. 51 2008 659 665
3. C. Lipinski Drug-like properties and the causes of poor solubility and poor permeability J. Pharm. Sci. 44 2000 235 249
4. V.J. Stella, and K.W. Nti-Addae Prodrug strategies to overcome poor water solubility Adv. Drug Deliv. Rev. 59 2007 677 694
5. S.L. Morissette, Ö. Almarsson, M.L. Peterson, J.F. Remenar, M.J. Read, A.V. Lemmo, S. Ellis, M.J. Cima, and C.R. Gardner High-throughput crystallization: polymorphs, salts, co-crystals and solvates of pharmaceutical solids Adv. Drug Deliv. Rev. 56 2003 275 300
6. H. Gelderblom, J. Verweij, K. Nooter, and A. Sparreboom Cremophor EL: the drawbacks and advantages of vehicle selection for drug formulation Eur. J. Cancer 37 2001 1590 1598
7. E.L.G. Merisko-Liversidge Nanosizing for oral and parenteral drug delivery: a perspective on formulating poorly-water soluble compounds using wet media milling technology Adv. Drug Deliv. Rev. 63 2011 427 440
8. S. van Janssens, and G. van den Mooter Review: physical chemistry of solid dispersions J. Pharm. Pharmacol. 61 2009 1571 1586
9. H. Bunjes Lipid nanoparticles for the delivery of poorly water-soluble drugs J. Pharm. Pharmacol. 62 2010 1637 1645
10. T.M. Allen Liposomal drug formulations: rationale for development and what we can expect for the future Drugs 56 1998 747 756
11. J.R. Soedirman, E.A. de Bruijn, R.A. Maes, A. Hanck, and J. Grüter Pharmacokinetics and tolerance of intravenous and intramuscular phylloquinone (vitamin K1) mixed micelles formulation Br. J. Clin. Pharmacol. 41 1996 517 523
12. G. Wörle, B. Siekmann, M.H. Koch, and H. Bunjes Transformation of vesicular into cubic nanoparticles by autoclaving of aqueous monoolein/poloxamer dispersions Eur. J. Pharm. Sci. 27 2006 44 53
13. J. Kuntsche, K. Westesen, M. Drechsler, M.H.J. Koch, and H. Bunjes Supercooled smectic nanoparticles: a potential novel carrier system for poorly water soluble drugs Pharm. Res. 21 2004 1834 1843
14. K. Rosenblatt, H. Bunjes, A screening approach to determine the solubilization capacity of lipid nanoparticles for poorly water soluble drugs, poster abstract # 126. In: 6th World Meeting on Pharmaceutics, Biopharmaceutics and Pharmaceutical Technology, Barcelona, 2008, < http://www.pharmtech.tu-bs. de/cms/files/poster/2008/Rosenblatt-Abstract-PBPWorldMeetingBarcelona-2008.pdf >.
15. P.P. Constantinides, A. Tustian, and D.R. Kessler Tocol emulsions for drug solubilization and parenteral delivery Adv. Drug Deliv. Rev. 56 2004 1243 1255
16. K.J. Box, and J.E.A. Comer Using measured pKa, log P and solubility to investigate supersaturation and predict BCS class Curr. Drug Metab. 9 2008 869 878
17. K.A. Chu, and S.H. Yalkowsky Predicting aqueous solubility: the role of crystallinity Curr. Drug Metab. 10 2009 1184 1191
18. Y. Yamaoka, R.D. Roberts, and V.J. Stella Low-melting phenytoin prodrugs as alternative oral delivery modes for phenytoin: a model for other high-melting sparingly water-soluble drugs J. Pharm. Sci. 72 1983 400 405
19. C.J. Reichwald, Eine neue Variante der Heck-Reaktion zur Darstellung antileishmanieller Paullone. Dissertation, Braunschweig, 2008.
20. S. Kohfeld, Untersuchungen zur Synthese, biologischen Aktivität und Stabilität von Paullonen und verwandten d-annellierten [1]Benzazepinen. Dissertation, Braunschweig, 2006.
21. S. Iwata, T. Nishino, H. Inoue, N. Nagata, Y. Satomi, H. Nishino, and S. Shibata Antitumorigenic activities of chalcones (II). Photo-isomerization of chalcones and the correlation with their biological activities Biol. Pharm. Bull. 20 1997 1266 1270
22. A. Kanstrup, and O. Buchardt Photochemical cis-trans isomerization of furylacryloylpeptides and their different kinetic behavior as substrates for carboxypeptidase Y Anal. Biochem. 194 1991 41 44
23. E. Kupetz, H. Bunjes, Passive loading of lipid nanoparticles with poorly water soluble drugs, poster # 420. In: 25th European Colloid and Interface Society Meeting Berlin, 2011, < http://www.pharmtech.tu-bs.de/cms/files/ poster/2011/Kupetz-ECIS-2011.pdf >.
24. R. New, M. Chance, and S. Heath Antileishmanial activity of amphotericin and other antifungal agents entrapped in liposomes J. Antimicrob. Chemoth. 8 1981 371 381
25. Y. Rahman, E. Cerny, and K. Patel Differential uptake of liposomes varying in size and lipid composition by parenchyma and Kupffer cells of mouse liver Life Sci. 31 1982 2061 2071
26. A. Raz, C. Bucana, and W. Fogler Biochemical, morphological, and ultrastructural studies on the uptake of liposomes by murine macrophages Cancer Res. 41 1981 487 494
27. J. Torrado, R. Espada, M. Ballesteros, and S. Torrado-Santiago Amphotericin B formulations and drug targeting J. Pharm. Sci. 97 2008 2405 2425
28. V. Martena, R. Censi, E. Hoti, L. Malaj, and P. Di Martino A new nanospray drying method for the preparation of nicergoline pure nanoparticles J. Nanopart. Res. 14 2012 Article # 934
29. H. Kala, U. Haack, P. Pollandt, and G. Brezesinski Zur Polymorphie des Carbamazepins Acta Pharm. Technol. 32 1986 72 77
30. F.U. Krahn, and J.B. Mielck Relations between several polymorphic forms and the dihydrate of carbamazepine Pharm. Acta Helv. 62 1987 247 254
31. J. Bauer, S. Spanton, R. Henry, J. Quick, W. Dziki, W. Porter, and J. Morris Ritonavir: an extraordinary example of conformational polymorphism Pharm. Res. 18 2001 859 866