Amorphous azithromycin with improved aqueous solubility and intestinal membrane permeability

Drug Development and Industrial Pharmacy

Volumn 41, Issue 7, 2015, Pages 1100-1108

  Aucamp, Marique ^a   Odendaal, Roelf ^a   Liebenberg, Wilna ^a   Hamman, Josias ^a  

^a NORTH WEST UNIVERSITY   (South Africa)

Author keywords

Amorphous; apparent permeability coefficient; azithromycin; dissolution; solubility; vapor sorption

Indexed keywords

AZITHROMYCIN; HYDROGEN; HYDROXYL GROUP; WATER; ANTIINFECTIVE AGENT;

APPARENT PERMEABILITY; ARTICLE; CRYSTALLIZATION; DRUG PENETRATION; DRUG SOLUBILITY; HYDROGEN BOND; HYSTERESIS; IN VITRO STUDY; INFRARED SPECTROSCOPY; INTESTINAL MEMBRANE PERMEABILITY; MEMBRANE PERMEABILITY; PH; PHYSICAL CHEMISTRY; SCANNING ELECTRON MICROSCOPY; SMALL INTESTINE; THERMOGRAPHY; X RAY POWDER DIFFRACTION; ANIMAL; BIOAVAILABILITY; CHEMISTRY; COMPARATIVE STUDY; INTESTINE; INTESTINE ABSORPTION; MEDICINAL CHEMISTRY; METABOLISM; PERMEABILITY; PIG; PROCEDURES; SOLUBILITY;

ANIMALS; ANTI-BACTERIAL AGENTS; AZITHROMYCIN; BIOLOGICAL AVAILABILITY; CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; HYDROGEN-ION CONCENTRATION; INTESTINAL ABSORPTION; INTESTINES; PERMEABILITY; SOLUBILITY; SWINE;

EID: 84932615507     PISSN: 03639045     EISSN: 15205762     Source Type: Journal    
DOI: 10.3109/03639045.2014.931967     Document Type: Article

References (27)

1. Nakornchai S, Konthiang P. Activity of azithromycin or erythromycin in combination with antimalarial drugs against mulitdrug-resistant Plasmodium falciparum in vitro. Acta Tropica 2006;100:185-91.
2. Ferrara A, Dos Santos C, Cimbro M, Gialdroni Grassi G. Comparative antimicrobial activity and post-antibiotic effect of azithromycin, clarithromycin and roxithromycin against some respiratory pathogens. Int J Antimicrob Agents 1996;7:181-6.
3. Boonleang J, Panrat K, Tantana C, Krittathanmakul S, Jintapakorn W. Bioavailability and pharmacokinetic comparison between generic and branded azithromycin capsule: a randomised, double blind, 2-way cross-over in healthy male Thai volunteers. Clin Ther 2007;29:703-10.
4. th edn NF.
5. Adrjanowicz K, Zakowiecki D, Kaminski K, et al. Molecular dynamics in supercooled liquid and glassy states of antibiotics: azithromycin, clarithromycin and roxithromycin studied by dielectric spectroscopy. Advantages given by the amorphous state. Mol Pharm 2012;9:1748-63.
6. Montejo-Bernardo J, Garcia-Granda S, Bayod-Jasanada M, et al. An easy and general method for quantifying Azithromycin dihydrate in a matrix of amorphous Azithromycin. ARKIVOC 2005;(ix):321-31.
7. Arora SC, Sharma PK, Irchhaiya R, et al. Development, characterization and solubility of solid dispersions of azithromycin dihydrate by solvent evaporation method. J Adv Pharm Technol Res 2010;1:221-8.
8. Yu L. Amorphous pharmaceutical solids: preparation, characterization and stabilization. Adv Drug Deliv Rev 2007;48:27-42.
9. Ashford M. Assessment of biopharmaceutical properties. In: Aulton ME, ed. Pharmaceutics. The design and manufacture of medicines. New York (NY): Churchill Livingstone; 2007:304-23.
10. Berggren S, Hoogstraate J, Fagerholm U, Lennernäs H. Characterization of jejunal absorption and apical efflux of ropivacaine, lidocaine and bupivacaine in the rat using in situ and in vitro absorption models. Eur J Pharm Sci 2004;21:553-60.
11. Balimane PV, Chong S, Morrison RA. Current methodologies used for evaluation of intestinal permeability and absorption. J Pharmacol Toxicol Meth 2000;44:301-12.
12. Hunter J, Hirst BH. Intestinal secretion of drugs. The role of P-glycoprotein and related drug efflux systems in limiting oral drug absorption. Adv Drug Deliv Rev 1997;25:129-57.
13. Kerns EH, Di L. Drug-like properties, concepts, structure design and methods: from ADME to toxicity optimization. San Diego (CA): Academic Press; 2008:526.
14. Nožinć D, Milić A, Mikac L, et al. Assessment of macrolide transport using PAMPA, Caco-2 and MDCKII-hMDR1 assays. Croat Chem Acta 2010;83:323-31.
15. Neirinckx E, Vervaet C, Michiels J, et al. Feasibility of the Ussing chamber technique for the determination of in vitro jejunal permeability of passively absorbed compounds in different animal species. J Vet Pharmacol Ther 2010;34:290-7.
16. Odendaal RW, Aucamp ME, Liebenberg W. A novel reversed-phase LC method for quantitative detection of azithromycin in bulk drug and tablet formulations in various aqueous media. Pharmazie 2012;67:984-6.
17. Tukker JJ. In vitro methods for the assessment of permeability. In: Dressman JB, Lennernäs H, eds. Oral drug absorption, prediction and assessment. New York (NY): Marcel Dekker Inc.; 2000:51-72.
18. Hansen TS, Nilsen OG. Echinacea purpurea and P-Glycoprotein drug transport in Caco-2 cells. Phytother Res 2009;23:86-91.
19. Brittain HG. Methods for the characterization of polymorphs and solvates. In: Brittain HG, ed. Polymorphism in pharmaceutical solids. New York (NY): Marcel Dekker Inc.; 1999:227-78.
20. nd ed. New York (NY): Wiley & Sons LTD; 1999:480.
21. Gandhi R, Pillai O, Thilagavathi R, et al. Characterization of azithromycin hydrates. Eur J Pharm Sci 2002;16:175-84.
22. Yu L, Reutzel SM, Stephenson GA. Physical characterization of polymorphic drugs: an integrated characterization strategy. Pharm Sci Technol Today 1998;1:118-27.
23. Chieng N, Rades T, Aaltonen J. An overview of recent studies on the analysis of pharmaceutical polymorphs. J Pharm Biomed Anal 2011;55:618-44.
24. Wolf M, Walker JE, Kapsalis JG. Water vapor sorption hysteresis in dehydrated food. J Agr Food Chem 1972;20:1073-7.
25. Burnett D, Thielmann F, Booth J. Determining the critical humidity for moisture-induced phase transitions. Int J Pharm 2004;287:123-33.
26. Greco K, Bogner R. Solution-mediated phase transformation: significance during dissolution and implications for bioavailability. J Pharm Sci 2012;101:2996-3018.
27. Aucamp M, Stieger N, Barnard N, Liebenberg W. Solution-mediated phase transformation of different roxithromycin solid-state forms: implications on dissolution and solubility. Int J Pharm 2013;449:18-27.