Pharmacokinetics of raloxifene in male Wistar-Hannover rats: Influence of complexation with hydroxybutenyl-beta-cyclodextrin

International Journal of Pharmaceutics

Volumn 346, Issue 1-2, 2008, Pages 25-37

  Wempe, Michael F ^a,b   Wacher, Vincent J ^c   Ruble, Karen M ^a   Ramsey, Michael G ^a   Edgar, Kevin J ^d   Buchanan, Norma L ^a   Buchanan, Charles M ^a  

^a EASTMAN CHEMICAL COMPANY   (United States)

^b EAST TENNESSEE STATE UNIVERSITY   (United States)

^c Virginia Tech ^*  (United States)

^d VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

Bioavailability; Dissolution; Hydroxybutenyl beta cyclodextrin; Liquid chromatography mass spectrometry mass spectrometry; Pharmacokinetic studies; Raloxifene

Indexed keywords

CYCLODEXTRIN DERIVATIVE; DRUG METABOLITE; HYDROXYBUTENYL BETA CYCLODEXTRIN; MICROCRYSTALLINE CELLULOSE; RALOXIFENE; SAQUINAVIR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG CAPSULE; DRUG DETERMINATION; DRUG FORMULATION; DRUG METABOLISM; DRUG SOLUBILITY; HUMAN; HUMAN TISSUE; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; WISTAR RAT;

ANIMALS; BETA-CYCLODEXTRINS; BIOLOGICAL AVAILABILITY; DOGS; FEMALE; HUMANS; INTESTINES; LIVER; MACACA FASCICULARIS; MALE; MICE; MICE, INBRED STRAINS; MICROSOMES; MICROSOMES, LIVER; RALOXIFENE; RATS; RATS, INBRED STRAINS; SELECTIVE ESTROGEN RECEPTOR MODULATORS; SOLUBILITY;

EID: 36148994703     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2007.06.002     Document Type: Article

References (38)

1. Barone J.A., Moskivitz B.L., Guarnieri J., Hassell A.E., Colaizzi J.L., Bierman R.H., and Jessen L. Enhanced bioavailability of itraconazole in hydroxypropyl-beta-cyclodextrin solution versus capsules in healthy volunteers. Antimicrob. Agents Chemother. 42 (1998) 1862-1865
2. Buchanan C.M., Alderson S.R., Cleven C.D., Dixon D.W., Ivanyi R., Lambert J.L., Lowman D.W., Offerman R.J., Szejtli J., and Szente L. Synthesis and characterization of water-soluble hydroxybutenyl cyclodextrins. Carbohydr. Res. 327 (2002) 493-507
3. Buchanan C.M., Buchanan N.L., Edgar K.J., Lambert J.L., Posey-Dowty J.D., Ramsey M.G., and Wempe M.F. Solubilization and dissolution of tamoxifen-hydroxybutenyl cyclodextrin complexes. J. Pharm. Sci. 95 (2006) 2246-2255
4. Buchanan C.M., Buchanan N.L., Edgar K.J., Little J.L., Malcolm M.O., Ruble K.M., Wacher V.J., and Wempe M.F. Pharmacokinetics of tamoxifen after intravenous and oral dosing of tamoxifen-hydroxybutenyl-beta-cyclodextrin formulations. J. Pharm. Sci. 96 (2007) 644-660
5. Buchanan C.M., Buchanan N.L., Edgar K.J., and Ramsey M.G. Solubility and dissolution studies of antifungal drug:hydroxybutenyl-beta-cyclodextrin complexes. Cellulose 14 (2007) 35-47
6. Buchanan, C.M., Buchanan, N.L., Edgar, K.J., Klein, S., Little, J.L., Ruble, K.M., Wacher, V.J., Wempe, M.F., 2007c. Pharmacokinetics of itraconazole after intravenous and oral dosing of itraconazole-cyclodextrin formulations. J Pharm. Sci., in press.
7. Chen Q., Ngui J.S., Doss G.A., Wang R.W., Cai X., DiNinno F.P., Blizzard T.A., Hammond M.L., Stearns R.A., Evans D.C., Baillie T.A., and Tang W. Cytochrome p450 3a4-mediated bioactivation of raloxifene: irreversible enzyme inhibition and thiol adduct formation. Chem. Res. Toxicol. 15 (2002) 907-914
8. Connors K.A. The stability of cyclodextrin complexes in solution. Chem. Rev. 97 (1997) 1325-1357
9. Czock D., Keller F., Heringa M., and Rasche F.M. Raloxifene pharmacokinetics in males with normal and impaired renal function. Br. J. Clin. Pharm. 59 (2004) 479-482
10. Dodge J.A., Lugar C.W., Cho S., Short L.L., Sato M., Yang N.N., Spangle L.A., Martin M.J., Phillips D.L., Glasebrook A.L., Osborne J.J., Frolik C.A., and Bryant H.U. Evaluation of the major metabolites of raloxifene as modulators of tissue selectivity. J. Steroid Biochem. Molec. Biol. 61 (1997) 97-106
11. Harada A., and Kamachi M. Complex formation between poly(ethylene glycol) and α-cyclodextrin. Macromolecules 23 (1990) 2821-2823
12. Hirayama F., and Uekama K. Cyclodextrin-based controlled drug release system. Adv. Drug Del. Rev. 36 (1999) 125-141
13. Hochner-Celnikier D. Pharmacokinetics of raloxifene and its clinical application. Eur. J. Obstet. Gynecol. Reprod. Biol. 85 (1999) 23-29
14. Jeong E.J., Lin H., and Hu M. Disposition mechanisms of raloxifene in the human intestinal. Caco-2 Model. JPET 310 (2004) 376-385
15. Jeong E.J., Liu Y., Lin H., and Hu M. Species- and disposition model-dependent metabolism of raloxifene in gut and liver: role of UGT1A10. Drug Metab. Dispos. 33 (2005) 785-794
16. Kemp D.C., Fan P.W., and Stevens J.C. Characterization of raloxifene glucuronidation in vitro: contribution of intestinal metabolism to presystemic clearance. Drug Metab. Dispos. 30 (2002) 694-700
17. Little J.A., Lehman P.A., Nowell S., Samokyszyn V., and Radominska A. Glucuronidation of all-trans-retinoic acid and 5,6-epoxy-all-trans-retinoic acid: activation of rat liver microsomal UDP-glucuronosyltransferase activity by alamethicin. Drug Metab Dispos 25 (1997) 5-11
18. Little J.L., Wempe M.F., and Buchanan C.M. Liquid chromatography-mass spectrometry/mass spectrometry method development for drug metabolism studies: examining lipid matrix ionization effects in plasma. J. Chrom. B. 833 (2006) 219-230
19. Loftsson T., Fridriksdottir H., Olafsdottir B.J., and Gudmundsson O. Solubilization and stabilization of drugs through cyclodextrin complexation. Acta Pharmaceutica Nordica 3 (1991) 215-217
20. Loftsson T., Sigurdsson H.H., Masson M., and Schipper N. Preparation of solid drug/cyclodextrin complexes of acidic and basic drugs. Pharmazie 59 (2004) 25-29
21. Malmsten M. Surfactants and Polymers in Drug Delivery (2002), Marcel Dekker Inc.
22. Morello K.C., Wurz G.T., and DeGregorio M.W. Pharmacokinetics of selective estrogen receptor modulators. Clin. Pharmacokinet. 42 (2003) 361-372
23. Naseem A., Olliff C.J., Martini L.G., and Lloyd A.W. Effects of plasma irradiation on the wettability and dissolution of compacts of griseofulvin. Int. J. Pharm. 269 (2004) 443-450
24. Redenti E., Szente L., and Szejtli J. Drug/cyclodextrin/hydroxy acid multicomponent systems: properties and pharmaceutical applications. J. Pharm. Sci. 89 (2000) 1-8
25. Rideout D.C., and Breslow R. Hydrophobic acceleration of diels-alder reactions. J Am. Chem. Soc. 102 (1980) 7816-7817
26. Rowland M., and Tozer T.N. Clinical Pharmacokinetics Concepts and Applications. third edition (1994), Lippincott Williams and Wilkins
27. In: Stahl P.H., and Wermuth C.G. (Eds). Handbook of Pharmaceutical Salts Properties Selection and Use (2002), Wiley-VCH
28. Sternbach D.S., and Rossana D.M. Cyclodextrin catalysis in the intramolecular diels-alder reaction with the furan diene. J. Am. Chem. Soc. 104 (1982) 5853-5854
29. Szejtli J. Cyclodextrins in drug formulations: Part II. Pharmaceut. Technol. 15 (1991) 24-38
30. Szejtli J. Selectivity/structure correlation in cyclodextrin chemistry. Supramolecular Chem. 6 (1995) 217-223
31. Tukey R.H., and Strassburg C.P. Human udp-glucuronosyltransferases: metabolism, expression, and disease. Annu. Rev. Pharmacol. Toxiol. 40 (2000) 581-616
32. Uekama K., Hirayama F., and Irie T. Cyclodextrin drug carrier systems. Chem. Rev. 98 (1998) 2045-2076
33. Valero M., Carrillo C., and Rodriguez L.J. Ternary naproxen:β-cyclodextrin:polyethylene glycol complex formation. Int. J. Pharm. 265 (2003) 141-149
34. Walton K., Dorne J.L., and Renwick A.G. Uncertainty factors for chemical risk assessment: interspecies differences in glucuronidation. Food Chem. Toxicol. 39 (2001) 1175-1190
35. Wempe M.F., Buchanan C.M., Buchanan N.L., Edgar K.J., Hanley G.A., Ramsey M.G., Skotty J.S., and Rice P.J. Pharmacokinetics of letrozole in male and female rats: influence of complexation with hydroxybutenyl-beta-cyclodextrin. JPP 59 (2007) 795-802
36. Wong S.M., Kellaway I.W., and Murdan S. Enhancement of the dissolution rate and oral absorption of a poorly water soluble drug by formation of surfactant-containing microparticles. Int. J. Pharm. 317 (2006) 61-68
37. Yu L., Liu H., Li W., Zhang F., Luckie C., van Breemen R.B., Thatcher R.J., and Bolton J.L. Oxidation of raloxifene to quinoids: potential toxic pathways via a diquinone methide and o-quinones. Chem. Res. Toxicol. 17 (2004) 879-888
38. Zweigenbaum J., and Henion J. Bioanalytical high-throughput selected reaction monitoring-LC/MS determination of selected estrogen receptor modulators in human plasma: 2000 samples/day. Anal. Chem. 72 (2000) 2446-2454