Effect of para-sulfonato-calix[n]arenes on the solubility, chemical stability, and bioavailability of a water insoluble drug nifedipine

Current Drug Discovery Technologies

Volumn 5, Issue 2, 2008, Pages 129-139

  Yang, Wenzhan ^a   Otto, Daniel P ^b   Liebenberg, Wilna ^c   De Villiers, Melgardt M ^b  

^a ASTRAZENECA   (United Kingdom)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

^c NORTH WEST UNIVERSITY   (South Africa)

Author keywords

Nifedipine; Para sulphonato calix n arenes; Pharmacokinetics; Solubility; Stability

Indexed keywords

CALCIUM CHANNEL BLOCKING AGENT; CALIXARENE; CYTOCHROME P450 3A; NIFEDIPINE; PYRIDINE DERIVATIVE; SULFONIC ACID DERIVATIVE;

ANIMAL EXPERIMENT; ARTICLE; BIOEQUIVALENCE; COMPLEX FORMATION; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG DEGRADATION; DRUG FORMULATION; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; ENZYME ACTIVITY; MALE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; RAT; THERMAL ANALYSIS;

ADMINISTRATION, ORAL; ANIMALS; BIOLOGICAL AVAILABILITY; CALCIUM CHANNEL BLOCKERS; CALIXARENES; CALORIMETRY, DIFFERENTIAL SCANNING; CHEMISTRY, PHARMACEUTICAL; CYTOCHROME P-450 CYP3A; DRUG CARRIERS; DRUG STABILITY; HYDROGEN-ION CONCENTRATION; INJECTIONS, INTRAVENOUS; LIVER; MALE; METHYLCELLULOSE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NIFEDIPINE; POLYETHYLENE GLYCOLS; RATS; RATS, SPRAGUE-DAWLEY; SOLUBILITY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TECHNOLOGY, PHARMACEUTICAL; THERAPEUTIC EQUIVALENCY; THERMOGRAVIMETRY;

EID: 45849126734     PISSN: 15701638     EISSN: None     Source Type: Journal    
DOI: 10.2174/157016308784746265     Document Type: Article

References (38)

1. Yang W., De Villiers M.M.: Aqueous solubilization of furosemide by supramolecular complexation with 4-sulphonic calix[n]arenes. J. Pharm. Pharmacol. 56, 703-708, (2004).
2. Yang W., De Villiers M.M.: The solubilization of the poorly water soluble drug nifedipine by water soluble 4-sulphonic calix[n]arenes. Eur. J. Pharm. Biopharm. 58, 629-636, (2004).
3. Yang W., De Villiers M.M.: Effect of 4-sulphonato-calix[n]arenes and cyclodextrins on the solubilization of niclosamide a poorly water soluble anthelmintic. AAPS J. 7(1), E241-E248, (2005).
4. Da Silva E., Lazar A.N., Coleman A.W.: Biopharmaceutical applications of calixarenes. J. Drug Deliv. Sci. Technol. 14(1), 3-20, (2004).
5. Perret F., Lazar A.N., Coleman A.W.: Biochemistry of the para-sulfonatocalix[n]arenes. Chem. Commun. (23), 2425-2438, (2006).
6. Paclet M-H., Rousseau C.F., Yannick C., Morel F., Coleman A.W.: An absence of non-specific immune response towards para-sulphonato-calix[n]arenes. J. Incl. Phenom. Macrocyclic Chem. 55(3-4), 353-357, (2006).
7. Gutsche C.D. In: Calixarenes Revisited. Monographs in Supramolecular Chemistry No. 1; Stoddart J.F. (Ed.), The Royal Society of Chemistry: Hertfordshire, SG (1998).
8. Da Silva E., Shahgaldian P., Coleman A.W.: Hemolytic properties of some water-soluble para-sulfonato-calix-[n]-arenes. Int. J. Pharm. 273(1-2), 57-62, (2004).
9. Da Silva E., Rousseau C.F., Zanella-Cleon I., Becchi M., Coleman A.W.: Mass Spectrometric Determination of Association Constants of Bovine Serum Albumin (BSA) with para-Sulfonato-Calix[n]arene Derivatives. J. Incl. Phenom. Macrocyclic Chem. 54(1-2), 53-59, (2006).
10. Ali S.L.: Analytical Profile of Nifedipine. In: Analytical Profiles of Drug Substances. Florey K. (Ed.), Academic Press, Inc.: New York, Vol 18, pp. 223-288, (1988).
11. Helin-Tanninen M., Naaranlahti T., Kontra K., Ojanen T.: Enteral suspension of nifedipine for neonates. Part 2. Stability of an extemporaneously compounded nifedipine suspension. J. Clin. Pharm. Ther. 26, 59-66, (2001).
12. Misik V., Tong M.I., Weglicki W.B.: Formation of superoxide in the reaction of photolytically altered nifedipine - a nitroso compound - with unsaturated membrane lipids. Chemico-Biol. Inter. 83, 97-105, (1992).
13. Thoma K., Klimek R.: The photoinstability of nifedipine. Part 3. Photostabilization of nifedipine in pharmaceutical formulations. Pharm. Ind. 53, 388-396, (1991).
14. Mielcarek J., Sadaj A.: Inclusion compounds of nifedipine and other 1,4-dihydropyridine derivatives with β-cyclodextrins. II. Photochemical stability of the inclusion compounds formed by nifedipine with β -cyclodextrins. Acta Pol. Pharm. 51, 21-24, (1994).
15. Karakhanov E.E., Maksimov A.L., Runova E.A., Kardasheva Y.S., Terenina M.V., Buchneva T.S., Guchkova A.Y.: Supramolecular catalytic systems based on calixarenes and cyclodextrins. Macromolecular Symposia, 204 IUPAC 10th Int. Symp. Macromol. Metal Comp. 159-173, (2003).
16. Gutsche C.D., Alam I.: Calixarenes. 23. The complexation and catalytic properties of water soluble calixarenes. Tetrahedron 44, 4689-4694, (1988).
17. Nomura E., Taniguchi H., Otsuji Y.: Calixarene-catalyzed permanganate oxidation of organic compounds. Bull. Chem. Soc. Jpn. 67, 309-311, (1994).
18. Shinkai S., Koreishi H., Ueda K., Arimura T., Manabe O.: Influence of hexasulfonated calix[6]arenes on the reactivities of arenediazonium ions in an aqueous system. Bull. Chem. Soc. Jpn. 60, 3679-3685, (1987).
19. Shinkai S., Shirahama Y., Tsubaki T., Manabe O.: Calixarene-catalyzed basic hydrolysis of p-nitrophenyl dodecanoate: a possible change in the mechanism from deshielding to host-guest. J. Am. Chem. Soc. 111, 5477-5478, (1989).
20. Shinkai S., Shirahama Y., Tsubaki T., Manabe O.: Cationic water-soluble calixarenes: new host molecules which catalyze basic hydrolysis of a phosphate ester. J. Chem. Soc. Perkin Trans.1. 10, 1859-1860, (1989).
21. Maksimov A.L., Buchneva T.S., Karakhanov E.A.: Supramolecular calixarene-based catalytic systems in the Wacker-oxidation of higher alkenes. J. Mol. Cat. A: Chem. 217, 59-67, (2004).
22. Shahriyar S.M., Lau-Cam C.A.: A simple HPLC method with spectrophotometric detection for the simultaneous assay of nifedipine and verapamil in rat plasma. J. Liq. Chrom. Rel. Technol. 23(8), 1253-1265, (2000).
23. Devarakonda B., De Villiers M.M.: Development and validation of an HPLC method involving solid-phase extraction for the analysis of hydrophobic drugs in the presence of polyamidoamine (PAMAM) dendrimers. J. Liq. Chrom. Rel. Technol. 28, 2325-2338, (2005).
24. [24 Upton R.A: Simple and reliable method for serial sampling of blood from rats. J. Pharm. Sci. 65, 112-114, (1987).
25. Caira M.R., Robbertse Y., Bergh J.J., De Villiers M.M.: Structural characterization, physicochemical properties, and thermal stability of three crystal forms of nifedipine. J. Pharm. Sci. 92(12), 2519-2533, (2003).
26. Yang W., Manek R.V., Kolling W.M., Brits M., Liebenberg W., De Villiers M.M.: Physiochemical characterization of water-soluble p-sulphonatocalix[n] arenes: Thermal, structural and sorption properties. Supramol. Chem. 17(6), 485-496, (2005).
27. Testa R., Dolfini E., Reschiotto C., Secchi C., Biondi P.A.: GLC determination of nifedipine, a light sensitive drug, in plasma. Il Farmaco 34, 463-473, (1979).
28. Jakobsen P., Lederballe Pederson O., Mikkelson E.J.: Gas chromatographic determination of nifedipine and one of its metabolites using electron capture detection. J. Chromatogr. 162, 81-87, (1979).
29. Pietta P., Rava A., Biondi P.: High-performance liquid chromatography of nifedipine, its metabolites and photochemical degradation products. J. Chromatogr. 210, 516-521, (1981).
30. Squella J.A., Barnafi E., Perna S., Nunez-Vergara L.J.: Nifedipine: differential pulse polarography and photodecomposition. Talanta 36, 363-366, (1989).
31. Hayase N., Itagaki Y.-I, Ogawa S., Akutsu S., Inagaki S.-I., Abiko Y.: Newly discovered photodegradation products of nifedipine in hospital prescriptions. J. Pharm. Sci. 83, 532-538, (1994).
32. Grundy J.S., Eliot L.A., Foster E.R.: Extrahepatic first-pass metabolism of nifedipine in the rat. Biopharm. Drug Dispos. 18, 509-522, (1997).
33. Iwao T., Inoue K., Hayashi Y., Yuasa H., Watanabe J.: Metabolic extraction of nifedipine during absorption from rat small intestine. Drug Metab. Pharmacokinet. 17, 546-553, (2002).
34. Kondo S., Sugimoto I.: Moment analysis of intravenous, intraduodenal, buccal, rectal and percutaneous nifedipine in rats. J. Pharmacobio-Dynam. 10, 462-469, (1987).
35. Bailey D.G., Spence J.D., Munoz C., Arnold J.M.O.: Interaction of citrus juices with felodipine and nifedipine. Lancet 337, 268-269, (1991).
36. Cummins C.L., Wu C.Y., Benet L.Z.: Sex-related differences in the clearance of cytochrome P450 3A4 substrates may be caused by P-glycoprotein. Clin. Pharmacol. Ther. 72, 474-489, (2002).
37. Zhang Y., Benet L.Z.: The gut as a barrier to drug absorption - Combined role of cytochrome P450 3A and P-glycoprotein. Clin. Pharmacokinet. 40, 159-168, (2001).
38. Emara L.H., Badr R.M., Elbary A.A: Improving the dissolution and bioavailability of nifedipine using solid dispersions and solubilizers. Drug Dev. Ind. Pharm. 28(7), 795-807, (2002).