Hydroxypropyl-beta-cyclodextrin

M. Ressing, W. Jiskoot, H. Talsma, C. van Ingen, E. Beuvery, and D. Crommelin, The influence of sucrose, dextran, and hydroxypropyl-beta-cyclodextrin as lyoprotectants for freeze-dried mouse IgG2a monoclonal antibosy (MN12), Pharm. Res., 9, 266... 

Hora et al. [3.19] described the complexity of protein stabilization by the example of recombinant, human Interleukin-2 (rhIL-2). Formulations with amino acids and mannitol/ sucrose are sensitive to mechanical stress e. g. by pumping. Hydroxypropyl-beta-cyclodextrin (HPcD) provides stability, but increases the sensitivity to oxygen. Polysor-bate 80 forms a mechanically stable product, but results in oxidation. In both cases contamination in the HPcD or traces of H202 in the Polysorbate may have been the starter for the oxidation. Brewster [3.20] reports, that HPcD stabilizes interleukin without forming aggregations and this results in 100 % biopotency. 

SG Penn, DM Goodall, JS Loran. Differential binding of tioconazole enantiomers to hydroxypropyl-beta-cyclodextrin studied by capillary electrophoresis. J Chromatogr 636 149-152, 1993. 

Z. Zuo, G. Kwon, B. Stevenson, J. Diakur, L.l. Wiebe, Flutamide—Hydroxypropyl-beta-cyclodextrin complex Formulation, physical characterization, and absorption studies using the Caco-2 in vitro model, J. Pharm. Pharm. Scl. 3 (2000) 220-227. 

Miyake, K. et al., Improvement of solubility and oral bioavailability of rutin by complexation with 2-hydroxypropyl-beta-cyclodextrin, Pharm. Dev. Technol, 5, 399, 2000. 

Van de Velde VJ, Van Peer AP, Heykants JJ, V foestenborghs RJ, Van Rooy P, De Beule KL, Cauwenbergh GF. Effect of food on the pharmacokinetics of a new hydroxypropyl-beta-cyclodextrin formulation of itraconazolePharmacotherapy, 1996 16 424-428. 

Jug, M., and M. Becirevic-Lacan. 2004. Influence of hydroxypropyl-beta-cyclodextrin complex-ation on piroxicam release from buccoadhesive tablets. Eur J Pharm Sci 21 251. 

Tirucherai, G.S., and A.K. Mitra. 2003. Effect of hydroxypropyl beta cyclodextrin complexation on aqueous solubility, stability, and corneal permeation of acyl ester prodrugs of gancyclovir. AAPS Pharm Sci Tech 4 E45. 

Aktas, Y. 2003. Influence of hydroxypropyl beta-cyclodextrin on the corneal permeation of pilocarpine. Drug Dev Ind Pharm 29 223. 

Brewster, M.E. Use of 2-hydroxypropyl-beta-cyclodextrin (HPCD) as a solubilizing and stabilizing excipient for protein drugs. Pharrn. Res. 8, 792-795,1991... 

Menges, R.A., Armstrong, D.W. (1991) Use of a three-phase model with hydroxypropyl-beta-cyclodextrin for the direct determination of large octanol-water and cyclodextrin-water partition coefficients. Anal Chim. Acta 255, 157-162. 

Boudad, H., Legrand, P., I.cBas, G., Cheron, M., Duchene D., and Ponchel, G. (2001), Combined hydroxypropyl-beta-cyclodextrin and poly(alkylcyanoacrylate) nanoparticles intended for oral administration of saquinavir, Int. J. Pharm., 218,113-124. 

Kimura, K., Hirayama, F, Arima, H. and Uekama, K. (2000). Effects of ageing on crystallization, dissolution, and absorption characteristics of amorphous tolbutamide-2-hydroxypropyl-beta-cyclodextrin complex. Chem. Pharm. Bull, 48, 646-50. [254]... 

Uekama, K. Ikegami, K. Wang, Z. Horiuchi, Y. Hirayama, F. Inhibitory effect of 2-hydroxypropyl-beta-cyclodextrin on crystal growth of nifedipine during storage superior dissolution and oral bioavailability compared with polyvinylpyrrolidone K-30. J. Pharm. Pharmacol. 1992, 44 (2), 73-78. 

Barone JA, Moskovitz BL, Guamieri J, Hassell AE, Colaizzi JL, Bierman RH, lessen L. Enhanced bioavailability of itraconazole in hydroxypropyl-beta-cyclodextrin solution versus capsules in healthy volunteers. Antimicrob Agents Chemother 1998 42(7) 1862-5. 

Glasmacher A, Hahn C, Molitor E, Marklein G, Sauerbruch T, Schmidt-Wolf IG. Itraconazole through concentrations in antifungal prophylaxis with six different dosing regimens using hydroxypropyl-beta-cyclodextrin oral solution or coated-pellet capsules. Mycoses 1999 42(ll-12) 591-600. 

Cyclodextrins have been used for enhancing the solubility of poorly water-soluble small molecules (Shimpi et ah, 2005). The mechanism of solubilization is formation of reversible complexes between the hydrophobic moiety of the drug molecule and the hydrophilic cyclodextrin that is highly water soluble. A similar observation has been made with some proteins and peptides (Brewster et ah, 1991 Johnson et ah, 1994 Flores et ah, 2001). Sulfated cyclodextrins and 2-hydroxypropyl-beta-cyclodextrins are approved excipients for parenteral administration, however, use of these compounds should take into consideration the cost involved. 

Lin, H.S., Chan, S.Y., Ng, Y.Y., and Ho, P.C. (2000) 2-Hydroxypropyl-beta-cyclodextrin increases aqueous solubility and photostability of all-trans retinoic acid, J. Clin. Pharm. Then, 25, 265-269. 

O. Reer and B. W. Muller, Investigation of the influence of cosolvents and surfactants on the complexation of dexamethasone with hydroxypropyl-beta-cyclodextrin by use of a simplex lattice design. Eur. J. Pharm. Biopharm., 39, 105-111 (1993). 

The effects of complexation and stabilization of 2, 3 -dideoxy-adenosine (I) with 2-hydroxypropyl-beta-cyclodextrin (II) were studied, and the results of kinetic studies and pKa determinations are reported. Although hydrolysis is 100% suppressed in both the protonated and neutral complexes, due to the small binding constants, the maximum stabilization attainable in a 0.1 M solution of II at 25 °C was approximately 5-fold at pH 5 and 2-fold at pH 2. Possible inclusion geometries are considered in an attempt to account for the kinetic data. 

Bizzigotti GO, Reynolds DA, Kueper BH. (1997). Enhanced solubilization and destruction of tetrachloroethylene by hydroxypropyl-beta-cyclodextrin and iron. Environmental... 

Ko SO, Schlautman MA, Carraway ER. (1999). Partitioning of hydrophobic organic compounds to hydroxypropyl-beta-cyclodextrin Experimental studies and model predictions for surfactant-enhanced remediation applications. Environmental Science and Technology 33 2765-2770. 

Rodriguez-Perez, A.I., Rodriguez-Tenreiro, C., Alvarez-Lorenzo, C. et al. 2006. Sertaconazole/hydroxypropyl-beta-cyclodextrin complexation Isothermal titration calorimetry and solubihty approaches. 7 Pharm Sci. 95 1751-1762. 

Yuan, C and ZY Jin (2008). Preparation and stabihty of the inclusion complex of astaxanthin with hydroxypropyl-beta-cyclodextrin. Pood Chemistry, 109(2), 264-268. 

Bai, YX, B Yu, XM Xu, ZY Jin and YQ Tian (2010). Comparison of encapsulation properties of major garlic oil components by hydroxypropyl beta-cyclodextrin. European Food Research and Technology, 231,519-524. 

Agueros et al. have reported the effect of the combination between 2-hydroxypropyl-beta-cyclodextrin and bioadhesive polyanhydride nanoparticles on the encapsulation and intestinal permeability of paclitaxel. A solid inclusion complex between dmg and cyclodextrin was prepared by an evaporation method. The complex was incorporated into polyanhydride nanoparticles. The association between these three components induces a positive effect over the intestinal permeability of paclitaxel (Agueros et al., 2009). 

Agueros, M., Ruiz-Gaton, L., Vauthier, C., Bouchemal, K., Espuelas, S., Ponchef G., Irache, J.M., 2009. Combined hydroxypropyl-beta-cyclodextrin and poly(anhydride) nanoparticles improve the oral permeability of paclitaxel. European Journal of Pharmaceutical Sciences 38, 405—413. 

Brewster ME, Vandecruys R, Peeters J, Neeskens P, Verreck G, Loftsson T (2008) Comparative interaction of 2-hydroxypropyl-beta-cyclodextrin and sulfobutylether-beta-cyclodextrin with itraconazole phase-solubility behavior and stabilization of supersaturated drug solutions. Eur J Pharm Sci 34 94-103... 

Mura P, Maestrelli F, Cirri M (2003) Ternary systems of naproxen with hydroxypropyl-p-cyclodextrin and aminoacids. Int J Pharm 260 293-302 Mura P, Bettinetti GP, Cirri M, Maestrelli F, Sorrenti M, Catenacci L (2(X)5) Solid-state chtirac-terization and dissolution properties of Naproxen-Arginine-Hydroxypropyl-[beta]-cyclodextrin ternary system. Eur J Pharm Biopharm 59 99-106 Newman A, Knipp G, Zografi G (2012) Assessing the performance of amorphous solid dispersions. J Pharm Sci 101 1355-1377... 

B. Cappello, C. Carmignani, M. lervohno, M.L La Rotonda, and M.F. Saettone, Solubilization of tropicamide by hydroxypropyl-beta-cyclodextrin and water-soluble polymers In vitro/in vivo studies, Int. J. Pharm., 213 (1-2), 75-81,2001. 

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