The influence of co-solvents on the stability and bioavailability of rapamycin formulated in self-microemulsifying drug delivery systems

References

• Sehgal SN. (2003). Sirolimus: its discovery, biological properties, and mechanism of action. Transplant Proc, 35:7S–14S.
   PubMed Web of Science ®Google Scholar
• Sehgal SN. (1998). Rapamune (RAPA, rapamycin, sirolimus): mechanism of action immunosuppressive effect results from blockade of signal transduction and inhibition of cell cycle progression. Clin Biochem, 31:335–340.
   PubMed Web of Science ®Google Scholar
• Soliman GA. (2005). The mammalian target of rapamycin signaling network and gene regulation. Curr Opin Lipidol, 16:317–323.
   PubMed Web of Science ®Google Scholar
• Castroagudín JF, Molina E, Tomé S, Otero E, Rodríguez M, Varo E. (2009). Safety of an immunosuppressant protocol based on sirolimus in liver transplant recipients with malignancies or high risk of tumor recurrence. Transplant Proc, 41:1003–1004.
   PubMed Web of Science ®Google Scholar
• Eng CP, Sehgal SN, Vézina C. (1984). Activity of rapamycin (AY-22,989) against transplanted tumors. J Antibiot, 37:1231–1237.
   PubMed Web of Science ®Google Scholar
• Seeliger H, Guba M, Koehl GE, Doenecke A, Steinbauer M, Bruns CJ et al. (2004). Blockage of 2-deoxy-d-ribose-induced angiogenesis with rapamycin counteracts a thymidine phosphorylase-based escape mechanism available for colon cancer under 5-fluorouracil therapy. Clin Cancer Res, 10:1843–1852.
   PubMed Web of Science ®Google Scholar
• Vignot S, Faivre S, Aguirre D, Raymond E. (2005). mTOR-targeted therapy of cancer with rapamycin derivatives. Ann Oncol, 16:525–537.
   PubMed Web of Science ®Google Scholar
• Yu K, Toral-Barza L, Discafani C, Zhang WG, Skotnicki J, Frost P et al. (2001). mTOR, a novel target in breast cancer: the effect of CCI-779, an mTOR inhibitor, in preclinical models of breast cancer. Endocr Relat Cancer, 8:249–258.
   PubMed Web of Science ®Google Scholar
• Trepanier DJ, Gallant H, Legatt DF, Yatscoff RW. (1998). Rapamycin: distribution, pharmacokinetics and therapeutic range investigations: an update. Clin Biochem, 31:345–351.
   PubMed Web of Science ®Google Scholar
• Yatscoff RW, Wang P, Chan K, Hicks D, Zimmerman J. (1995). Rapamycin: distribution, pharmacokinetics, and therapeutic range investigations. Ther Drug Monit, 17:666–671.
   PubMed Web of Science ®Google Scholar
• Kahan BD. (2002). Update on pharmacokinetic/pharmacodynamic studies with FTY720 and sirolimus. Ther Drug Monit, 24:47–52.
   PubMed Web of Science ®Google Scholar
• Laplante A, Demeule M, Murphy GF, Béliveau R. (2002). Interaction of immunosuppressive agents rapamycin and its analogue SDZ-RAD with endothelial P-gp. Transplant Proc, 34:3393–3395.
   PubMed Web of Science ®Google Scholar
• Sattler M, Guengerich FP, Yun CH, Christians U, Sewing KF. (1992). Cytochrome P-450 3A enzymes are responsible for biotransformation of FK506 and rapamycin in man and rat. Drug Metab Dispos, 20:753–761.
   PubMed Web of Science ®Google Scholar
• Simamora P, Alvarez JM, Yalkowsky SH. (2001). Solubilization of rapamycin. Int J Pharm, 213:25–29.
   PubMed Web of Science ®Google Scholar
• Wacher VJ, Wu CY, Benet LZ. (1995). Overlapping substrate specificities and tissue distribution of cytochrome P450 3A and P-glycoprotein: implications for drug delivery and activity in cancer chemotherapy. Mol Carcinog, 13:129–134.
   PubMed Web of Science ®Google Scholar
• Kang BK, Lee JS, Chon SK, Jeong SY, Yuk SH, Khang G et al. (2004). Development of self-microemulsifying drug delivery systems (SMEDDS) for oral bioavailability enhancement of simvastatin in beagle dogs. Int J Pharm, 274:65–73.
   PubMed Web of Science ®Google Scholar
• Kim HJ, Yoon KA, Hahn M, Park ES, Chi SC. (2000). Preparation and in vitro evaluation of self-microemulsifying drug delivery systems containing idebenone. Drug Dev Ind Pharm, 26:523–529.
   PubMed Web of Science ®Google Scholar
• Patel D, Sawant KK. (2007). Oral bioavailability enhancement of acyclovir by self-microemulsifying drug delivery systems (SMEDDS). Drug Dev Ind Pharm, 33:1318–1326.
   PubMed Web of Science ®Google Scholar
• Shen H, Zhong M. (2006). Preparation and evaluation of self-microemulsifying drug delivery systems (SMEDDS) containing atorvastatin. J Pharm Pharmacol, 58:1183–1191.
   PubMed Web of Science ®Google Scholar
• Venkatesh G, Majid MI, Mansor SM, Nair NK, Croft SL, Navaratnam V. (2010). In vitro and in vivo evaluation of self-microemulsifying drug delivery system of buparvaquone. Drug Dev Ind Pharm, 36:735–745.
   PubMed Web of Science ®Google Scholar
• Wu W, Wang Y, Que L. (2006). Enhanced bioavailability of silymarin by self-microemulsifying drug delivery system. Eur J Pharm Biopharm, 63:288–294.
   PubMed Web of Science ®Google Scholar
• Wu X, Xu J, Huang X, Wen C. (2011). Self-microemulsifying drug delivery system improves curcumin dissolution and bioavailability. Drug Dev Ind Pharm, 37:15–23.
   PubMed Web of Science ®Google Scholar
• Zhang P, Liu Y, Feng N, Xu J. (2008). Preparation and evaluation of self-microemulsifying drug delivery system of oridonin. Int J Pharm, 355:269–276.
   PubMed Web of Science ®Google Scholar
• Sun MH, Zhai XZ, Si LQ, Li G., Yang XL. (2010). Formulation design and evaluation of self-microemulsifying drug delivery system of rapamycin. Clin Pharm J, 45:193–198.
   Google Scholar
• Luengo JI, Konialian AL, Holt DA, Luengo JI. (1993). Studies on the chemistry of rapamycin: novel transformations under Lewis-acid catalysis. Tetrahedron Lett, 34:991–994.
   Web of Science ®Google Scholar
• Steffan RJ, Kearney RM, Hu DC, Failli AA, Skotnicki JS, Schiksnis RA, Mattes JF, Chan KW, Caufield CE. (1993). Base catalyzed degradations of rapamycin. Tetrahedron Lett, 34:3699–3702.
   Web of Science ®Google Scholar
• Yohannes D, Myers CD, Danishefsky SJ. (1993). Degradation of rapamycin: synthesis of a rapamycin derived fragment containing the tricarbonyl and triene sectors. Tetrahedron Lett, 34:2075–2078.
   Web of Science ®Google Scholar
• Caufield CE. (1995). Structure–activity relationships involving modifications to the macrolides FK-506 and rapamycin. Curr Pharm Des, 1:145–160.
   Google Scholar
• Sedrani R, Jones LH, Jutzi-Eme AM, Schuler W, Cottens S. (1999). Cleavage of the cyclohexyl-subunit of rapamycin results in loss of immunosuppressive activity. Bioorg Med Chem Lett, 9:459–462.
   PubMed Web of Science ®Google Scholar
• Rouf MA, Bilensoy E, Vural I, Hıncal AA. (2007). Determination of stability of rapamycin following exposure to different conditions. Eur J Pharm Sci, 32S:S22–S50.
   Google Scholar
• Il’ichev YV, Alquier L, Maryanoff CA. (2007). Degradation of rapamycin and its ring-opened isomer: role of base catalysis. ARKIVOC (Gainesville, FL, United States), 12:110–131.
   Google Scholar
• Fluttert M, Dalm S, Oitzl MS. (2000). A refined method for sequential blood sampling by tail incision in rats. Lab Anim, 34:372–378.
   PubMed Web of Science ®Google Scholar
• Custodio JM, Wu CY, Benet LZ. (2008). Predicting drug disposition, absorption/elimination/transporter interplay and the role of food on drug absorption. Adv Drug Deliv Rev, 60:717–733.
   PubMed Web of Science ®Google Scholar
• Porter CJ, Pouton CW, Cuine JF, Charman WN. (2008). Enhancing intestinal drug solubilisation using lipid-based delivery systems. Adv Drug Deliv Rev, 60:673–691.
   PubMed Web of Science ®Google Scholar
• Chakraborty S, Shukla D, Mishra B, Singh S. (2009). Lipid—an emerging platform for oral delivery of drugs with poor bioavailability. Eur j Pharm Biopharm, 73:1–15.
   PubMed Web of Science ®Google Scholar
• Bogman K, Zysset Y, Degen L, Hopfgartner G, Gutmann H, Alsenz J et al. (2005). P-glycoprotein and surfactants: effect on intestinal talinolol absorption. Clin Pharmacol Ther, 77:24–32.
   PubMed Web of Science ®Google Scholar
• Constantinides PP, Wasan KM. (2007). Lipid formulation strategies for enhancing intestinal transport and absorption of P-glycoprotein (P-gp) substrate drugs: in vitro/in vivo case studies. J Pharm Sci, 96:235–248.
   PubMed Web of Science ®Google Scholar
• Cui SX, Nie SF, Li L, Wang CG, Pan WS, Sun JP. (2009). Preparation and evaluation of self-microemulsifying drug delivery system containing vinpocetine. Drug Dev Ind Pharm, 35:603–611.
   PubMed Web of Science ®Google Scholar
• Martin-Facklam M, Burhenne J, Ding R, Fricker R, Mikus G, Walter-Sack I et al. (2002). Dose-dependent increase of saquinavir bioavailability by the pharmaceutic aid cremophor EL. Br J Clin Pharmacol, 53:576–581.
   PubMed Web of Science ®Google Scholar
• Tayrouz Y, Ding R, Burhenne J, Riedel KD, Weiss J, Hoppe-Tichy T et al. (2003). Pharmacokinetic and pharmaceutic interaction between digoxin and Cremophor RH40. Clin Pharmacol Ther, 73:397–405.
   PubMed Web of Science ®Google Scholar
• Chen ML. (2008). Lipid excipients and delivery systems for pharmaceutical development: a regulatory perspective. Adv Drug Deliv Rev, 60:768–777.
   PubMed Web of Science ®Google Scholar
• Wu CY, Benet LZ. (2005). Predicting drug disposition via application of BCS: transport/absorption/elimination interplay and development of a biopharmaceutics drug disposition classification system. Pharm Res, 22:11–23.
   PubMed Web of Science ®Google Scholar
• Van Duyne GD, Standaert RF, Karplus PA, Schreiber SL, Clardy J. (1993). Atomic structures of the human immunophilin FKBP-12 complexes with FK506 and rapamycin. J Mol Biol, 229:105–124.
   PubMed Web of Science ®Google Scholar
• Wandless TJ, Michnick SW, Rosen MK, Karplus M, Schreiber SL. (1991). FK506 and rapamycin binding to FKBP: common elements in immunophilin–ligand complexation. J Am Chem Soc, 113:2339–2341.
   Web of Science ®Google Scholar
• Nelson FC, Stachel SJ, Eng CP, Sehgal SN. (1999). Manipulation of the C(22)–C(27) region of rapamycin: stability issues and biological implications. Bioorg Med Chem Lett, 9:295–300.
   PubMed Web of Science ®Google Scholar