• 综述与评论 •
薛一凡, 孟文卉, 汪润泽, 任俊杰, 衡伟利, 张建军. 过饱和度理论及过饱和药物递送系统[J]. 化学进展, 2020, 32(6): 698-712.
Yifan Xue, Wenhui Meng, Runze Wang, Junjie Ren, Weili Heng, Jianjun Zhang. Supersaturation Theory and Supersaturating Drug Delivery System(SDDS)[J]. Progress in Chemistry, 2020, 32(6): 698-712.
在药物研发领域,如何有效提高难溶性药物的溶解与吸收是一个极具挑战的难题。目前,过饱和药物递送系统(Supersaturating drug delivery systems,SDDS)利用药物溶液处于过饱和态的优势,可同时提高难溶性药物的表观溶解度与渗透性。本文对过饱和度的理论及其在药物研发领域中的实际应用进行了系统的综述,介绍了过饱和度的产生与维持、及其与药物吸收的关系,归纳了常用的SDDS技术,并对无定形固体分散体、共晶、无定形/共无定形产生过饱和进行重点阐述。
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Drug | BCS | Trade Name | Preparation Method | Carrier or Coformer or CCF or Acid/Base | ref |
---|---|---|---|---|---|
Amorphous | |||||
Cefuroxime Axetil | Ⅱ | Ceftin? | |||
Nelfinavir Mesylate | Ⅱ | Viracept? | |||
Rosuvastatin Calcium | Ⅱ | Crestor? | |||
Quinapril Hydrochloride | Ⅱ | Accupril? | |||
Zafirlukast | Ⅱ | Accolate? | 162 | ||
ASD | |||||
Itraconazole | Ⅱ | Sporanox? | Spray-drying | HPMC | |
Lopinavir、Ritonavir | Ⅱ | Kaletra? | Melt-extrusion | PVPVA64 | |
Ritonavir | Ⅱ | Norvir? | Melt-extrusion | PVPVA64 | |
Griseofulvin | Ⅱ | Gris-PEG? | Melt-extrusion | PEG | |
Fenofibrate | Ⅱ | Fenoglide? | Spray-extrusion | PEG | |
Everolimus | Ⅱ | Certican? | Spray-drying | HPMC | |
Etravirine | Ⅳ | Intelence? | Spray-drying | HPMC | |
Celecoxib | Ⅱ | Spray-drying | PVP and SDS | ||
Itraconazole | Ⅱ | Spray-drying | HPMC-AS | ||
Ticagrelor | Ⅳ | Solvent Evaporation | TPGS and Neusilin? US2 | ||
Curcumin | Ⅳ | Co-milling | Chitosan Oligosaccharide | ||
Nobiletin | Ⅱ | Hot-melt Extrusion | Methyl Hesperidin | 166 | |
Co-amorphous | |||||
Docetaxel | Ⅳ | Rotary Vacuum Evaporation | Myricetin | ||
Docetaxel | Ⅳ | Vibrational Ball Milling | Bicalutamide | ||
Carvedilol | Ⅱ | Spray-drying | Aspartic Acid | ||
Lurasidone Hydrochloride | Ⅱ | Rotary Vacuum Evaporation | Saccharin | 50 | |
Indomethacin | Ⅱ | Hot-melt Extrusion and Spray-drying | Arginine and Copovidone | ||
Atorvastatin Calcium | Ⅱ | Solvent Evaporation | Nicotinamide | ||
Lurasidone Hydrochloride | Ⅱ | Solvent Evaporation | Repaglinide | ||
Atorvastatin Calcium | Ⅱ | Solvent Evaporation | Carvedilol | ||
Ritonavir | Ⅱ | Solvent Evaporation | Indomethacin | 135 | |
Co-crystal | |||||
Valsartan | Ⅱ | Entresto? | Sacubitril | ||
Ipragliflozin | Ⅱ | Suglat? | L-proline | ||
Sodium Valproate | Ⅱ | Epilim? | Valproic Acid | ||
Ketoconazole | Ⅱ | Slow Solvent Evaporation | Fumaric Acid | 54 | |
Oxyresveratrol | Ⅱ | Balls Milling | Citric Acid | ||
Acetazolamide | Ⅳ | Grinding and Solvent-Evaporation | Proline | ||
Hydrochlorothiazide | Ⅳ | Grinding | Nicotinamide | 147 | |
Crystal salts | |||||
Lurasidone Hydrochloride | Ⅱ | Latuda? | |||
Fingolimod Hydrochloride | Ⅱ | Gilenya? | |||
Ketoconazole | Ⅱ | Slow Solvent Evaporation | Oxalate Acid | 54 | |
Celecoxib | Ⅱ | Slow Solvent Evaporation | Sodium Hydroxide | 29 | |
Nanocrystal | |||||
Aprepitant | Ⅳ | Emend? | Wet Media Milling | ||
Sirolimus | Ⅱ | Rapamune? | Wet Media Milling | ||
Fenofibrate | Ⅱ | TriCor? | Wet Media Milling | ||
Megestrol Acetate | Ⅱ | Megace ES? | Wet Media Milling | ||
Itraconazole | Ⅱ | Rapid Wet Milling | 163 |
[1] |
Loftsson T, Brewster M E . J. Pharm. Pharmacol., 2010,62(11):1607. https://www.ncbi.nlm.nih.gov/pubmed/21039545
doi: 10.1111/j.2042-7158.2010.01030.x URL pmid: 21039545 |
[2] |
Amidon G L, Lennernas H, Shah V P , Crison J R. Pharm. Res., 1995,12(3):413. https://www.ncbi.nlm.nih.gov/pubmed/7617530
URL pmid: 7617530 |
[3] |
Streubel A, Siepmann J , Bodmeier R. Curr. Opin. Pharmacol., 2006,6(5):501. https://www.ncbi.nlm.nih.gov/pubmed/16890020
URL pmid: 16890020 |
[4] |
Tanaka N, Imai K, Okimoto K, Ueda S, Tokunaga Y, Ibuki R, Higaki K, Kimura T J . Control. Release, 2006,112(1):51. https://linkinghub.elsevier.com/retrieve/pii/S0168365906000411
doi: 10.1016/j.jconrel.2006.01.020 URL |
[5] |
Vippagunta S R, Wang Z R, Hornung S, Krill S L . J. Pharm. Sci., 2007,96(2):294. https://www.ncbi.nlm.nih.gov/pubmed/17051588
doi: 10.1002/jps.20754 URL pmid: 17051588 |
[6] |
Dahan A , Miller J M. AAPS J., 2012,14, 244. https://www.ncbi.nlm.nih.gov/pubmed/22391790
doi: 10.1208/s12248-012-9337-6 URL pmid: 22391790 |
[7] |
Katneni K, Charman S A, Porter C J . J. Pharm. Sci., 2006,95(10):2170. https://www.ncbi.nlm.nih.gov/pubmed/16883557
URL pmid: 16883557 |
[8] |
Katneni K, Charman S A , Porter C J. J. Pharm. Sci., 2007,96(2):280. https://www.ncbi.nlm.nih.gov/pubmed/17051595
doi: 10.1002/jps.20779 URL pmid: 17051595 |
[9] |
Mudra D R, Borchardt R T . J. Pharm. Sci., 2010,99(2):1016. https://www.ncbi.nlm.nih.gov/pubmed/19650119
URL pmid: 19650119 |
[10] |
Mudra D R, Jin J Y, Borchardt R T . J. Pharm. Sci., 2010,99(2):999. https://www.ncbi.nlm.nih.gov/pubmed/19798765
doi: 10.1002/jps.21965 URL pmid: 19798765 |
[11] |
Yano K, Masaoka Y, Kataoka M, Sakuma S, Yamashita S . J. Pharm. Sci., 2010,99(3):1336. https://www.ncbi.nlm.nih.gov/pubmed/19743502
doi: 10.1002/jps.21919 URL pmid: 19743502 |
[12] |
Amidon G E, Higuchi W I, Ho N F . J. Pharm. Sci., 1982,71(1):77. https://www.ncbi.nlm.nih.gov/pubmed/7057387
doi: 10.1002/jps.2600710120 URL pmid: 7057387 |
[13] |
Miller J M, Beig A, Krieg B J, Carr R A, Borchardt T B, Amidon G E, Amidon G L, Dahan A . Mol. Pharm., 2011,8(5):1848. https://www.ncbi.nlm.nih.gov/pubmed/21800883
URL pmid: 21800883 |
[14] |
Nerurkar M M, Ho N F, Burton P S, Vidmar T J, Borchardt R T . J. Pharm. Sci., 1997,86(7):813. https://www.ncbi.nlm.nih.gov/pubmed/9232522
URL pmid: 9232522 |
[15] |
Poelma F G, Breas R, Tukker J J, Crommelin D J . J. Pharm. Pharmacol., 1991,43(5):317. https://www.ncbi.nlm.nih.gov/pubmed/1680173
doi: 10.1111/j.2042-7158.1991.tb06697.x URL pmid: 1680173 |
[16] |
Serajuddin A T M . Adv. Drug Delivery Rev., 2007,59(7):603. https://linkinghub.elsevier.com/retrieve/pii/S0169409X07000816
doi: 10.1016/j.addr.2007.05.010 URL |
[17] |
Thakuria R, Delori A, Jones W, Lipert M P, Roy L , Rodriguez-Hornedo N. Int. J. Pharm., 2013,453(1):101. https://www.ncbi.nlm.nih.gov/pubmed/23207015
URL pmid: 23207015 |
[18] |
Newman A, Knipp G, Zografi G . J. Pharm. Sci., 2012,101(4):1355. https://www.ncbi.nlm.nih.gov/pubmed/22213468
URL pmid: 22213468 |
[19] |
Gursoy R N, Benita S . Biomed. Pharmacother., 2004,58(3):173. https://www.ncbi.nlm.nih.gov/pubmed/15082340
URL pmid: 15082340 |
[20] |
Anby M U, Williams H D , McIntosh M, Benameur H, Edwards G A, Pouton C W, Porter C J H. Mol. Pharm., 2012,9(7):2063. https://www.ncbi.nlm.nih.gov/pubmed/22656917
doi: 10.1021/mp300164u URL pmid: 22656917 |
[21] |
Williams H D, Trevaskis N L, Yeap Y Y, Anby M U, Pouton C W , Porter C J H. Pharm. Res., 2013,30(12):2976. https://www.ncbi.nlm.nih.gov/pubmed/23824582
doi: 10.1007/s11095-013-1126-0 URL pmid: 23824582 |
[22] |
Feeney O M, Crum M F , McEvoy C L, Trevaskis N L, Williams H D, Pouton C W, Charman W N, Bergstrom C A S, Porter C J H. Adv. Drug Delivery Rev., 2016,101: 167. https://linkinghub.elsevier.com/retrieve/pii/S0169409X16301065
doi: 10.1016/j.addr.2016.04.007 URL |
[23] |
Frank K J, Rosenblatt K M, Westedt U, Holig P, Rosenberg J, Magerlein M, Fricker G , Brandl M. Int. J. Pharm., 2012,437(1/2):288. https://linkinghub.elsevier.com/retrieve/pii/S0378517312008095
doi: 10.1016/j.ijpharm.2012.08.014 URL |
[24] |
Higuchi T J. Cosmet. Sci., 1960,11: 12.
|
[25] |
Raina S A , Zhang G G Z, Alonzo D E, Wu J W, Zhu D H, Catron N D, Gao Y, Taylor L S. Pharm. Res., 2015,32(10):3350. https://www.ncbi.nlm.nih.gov/pubmed/26017301
URL pmid: 26017301 |
[26] |
Brouwers J, Brewster M E, Augustijns P . J. Pharm. Sci., 2009,98(8):2549. https://www.ncbi.nlm.nih.gov/pubmed/19373886
doi: 10.1002/jps.21650 URL pmid: 19373886 |
[27] |
Mullin J W . Crystallization. Oxford: Butterworth-Heinemann, 2001. 123.
|
[28] |
Sousa L A E, Reutzel-Edens S M, Stephenson G A, Taylor L S . Cryst. Growth Des. 2016,16(2):737. https://pubs.acs.org/doi/10.1021/acs.cgd.5b01341
doi: 10.1021/acs.cgd.5b01341 URL |
[29] |
Guzman H R, Tawa M, Zhang Z, Ratanabanangkoon P, Shaw P, Gardner C R, Chen H, Moreau J P, Almarsson O, Remenar J F . J. Pharm. Sci., 2007,96(10):2686. https://www.ncbi.nlm.nih.gov/pubmed/17518357
doi: 10.1002/jps.20906 URL pmid: 17518357 |
[30] |
Wouters J, Quéré J. Pharmaceutical Salts and Co-crystals. Cambridge: RSC Publishing, 2012. 249.
|
[31] |
Miyako Y, Tai H, Ikeda K, Kume R , Pinal R. Drug Dev. Ind. Pharm., 2008,34(5):499. https://www.ncbi.nlm.nih.gov/pubmed/18473232
doi: 10.1080/03639040701744020 URL pmid: 18473232 |
[32] |
Miller J M, Beig A, Carr R A, Webster G K, Dahan A . Mol. Pharm., 2012,9(3):581. https://www.ncbi.nlm.nih.gov/pubmed/22280478
doi: 10.1021/mp200460u URL pmid: 22280478 |
[33] |
Gao P, Rush B D, Pfund W P, Huang T H, Bauer J M, Morozowich W, Kuo M S, Hageman M J . J. Pharm. Sci., 2003,92(12):2386. https://www.ncbi.nlm.nih.gov/pubmed/14603484
doi: 10.1002/jps.10511 URL pmid: 14603484 |
[34] |
Wei Y H, Ye X L, Shang X G, Peng X, Bao Q, Liu M C, Guo M M , Li F Z. Colloids Surf. A, 2012,396: 22. https://linkinghub.elsevier.com/retrieve/pii/S0927775711007710
doi: 10.1016/j.colsurfa.2011.12.025 URL |
[35] |
Pudipeddi M, Serajuddin A T . J. Pharm. Sci., 2005,94(5):929. https://www.ncbi.nlm.nih.gov/pubmed/15770643
URL pmid: 15770643 |
[36] |
Yu L . Adv. Drug Delivery Rev., 2001,48(1):27. https://linkinghub.elsevier.com/retrieve/pii/S0169409X01000989
doi: 10.1016/S0169-409X(01)00098-9 URL |
[37] |
Craig D Q, Royall P G, Kett V L , Hopton M L. Int. J. Pharm., 1999,179(2):179. https://www.ncbi.nlm.nih.gov/pubmed/10053213
doi: 10.1016/s0378-5173(98)00338-x URL pmid: 10053213 |
[38] |
Li D X, Oh Y K, Lim S J, Kim J O, Yang H J, Sung J H, Yong C S , Choi H G. Int. J. Pharm., 2008,355(1/2):277. https://linkinghub.elsevier.com/retrieve/pii/S0378517307010629
doi: 10.1016/j.ijpharm.2007.12.020 URL |
[39] |
Kaushal A M, Gupta P , Bansal A K. Crit. Rev. Ther. Drug Carrier Syst., 2004,21(3):133. https://www.ncbi.nlm.nih.gov/pubmed/15248808
URL pmid: 15248808 |
[40] |
Kim J S, Kim M S, Park H J, Jin S J, Lee S, Hwang S . J. Int. J. Pharm., 2008,359(1/2):211. https://linkinghub.elsevier.com/retrieve/pii/S0378517308002809
doi: 10.1016/j.ijpharm.2008.04.006 URL |
[41] |
Vasconcelos T, Sarmento B, Costa P . Drug Discov. Today, 2007,12(23/24):7.
|
[42] |
Zhang J J, Qian S, Gao Y. Theory and Practice of Polymorphic Drug Development. Beijing: Chemical Industry Press, 2019. 207.
|
[43] |
Shamblin S L, Taylor L S, Zografi G . J. Pharm. Sci., 1998,87(6):694. https://www.ncbi.nlm.nih.gov/pubmed/9607945
doi: 10.1021/js9704801 URL pmid: 9607945 |
[44] |
Miller J M, Beig A, Carr R A, Spence J K, Dahan A . Mol. Pharm., 2012,9(7):2009. https://www.ncbi.nlm.nih.gov/pubmed/22632106
doi: 10.1021/mp300104s URL pmid: 22632106 |
[45] |
Wang S, Liu C, Chen Y, Zhu A D, Qian F . Mol. Pharm., 2018,15(10):4643. https://www.ncbi.nlm.nih.gov/pubmed/30130968
doi: 10.1021/acs.molpharmaceut.8b00633 URL pmid: 30130968 |
[46] |
Jackson M J, Kestur U S, Hussain M A , Taylor L S. Mol. Pharm., 2016,13(1):223. https://www.ncbi.nlm.nih.gov/pubmed/26618718
doi: 10.1021/acs.molpharmaceut.5b00652 URL pmid: 26618718 |
[47] |
Kohri N, Yamayoshi Y, Xin H, Iseki K, Sato N, Todo S , Miyazaki K J. Pharm. Pharmacol., 1999,51(2):159. http://doi.wiley.com/10.1111/%28ISSN%292042-7158
doi: 10.1111/(ISSN)2042-7158 URL |
[48] |
Vasconcelos T, Sarmento B, Costa P . Drug Discov Today, 2007,12: 1068. https://www.ncbi.nlm.nih.gov/pubmed/18061887
doi: 10.1016/j.drudis.2007.09.005 URL pmid: 18061887 |
[49] |
Löbmann K, Grohganz H, Laitinen R, Strachan C , Rades T. Eur. J. Pharm. Biopharm., 2013,85: 873. https://www.ncbi.nlm.nih.gov/pubmed/23537574
doi: 10.1016/j.ejpb.2013.03.014 URL pmid: 23537574 |
[50] |
Qian S, Heng W L, Wei Y F, Zhang J J , Gao Y. Cryst. Growth Des., 2015,15(6):2920. https://pubs.acs.org/doi/10.1021/acs.cgd.5b00349
doi: 10.1021/acs.cgd.5b00349 URL |
[51] |
Good D J , Rodriguez-Hornedo N. Cryst. Growth Des., 2009,9(5):2252. https://pubs.acs.org/doi/10.1021/cg801039j
doi: 10.1021/cg801039j URL |
[52] |
Paulekuhn G S, Dressman J B, Saal C . J. Med. Chem., 2007,50(26):6665. https://www.ncbi.nlm.nih.gov/pubmed/18052022
URL pmid: 18052022 |
[53] |
Gao Y, Gao J, Liu Z L, Kan H L, Zu H, Sun W J, Zhang J J , Qian S. Int. J. Pharm., 2012,438(1/2):327. https://linkinghub.elsevier.com/retrieve/pii/S0378517312008927
doi: 10.1016/j.ijpharm.2012.09.027 URL |
[54] |
Martin F A, Pop M M, Borodi G, Filip X , Kacso I. Cryst. Growth Des., 2013,13(10):4295. https://pubs.acs.org/doi/10.1021/cg400638g
doi: 10.1021/cg400638g URL |
[55] |
Shiraki K, Takata N, Takano R, Hayashi Y, Terada K . Pharm. Res., 2008,25(11):2581. https://www.ncbi.nlm.nih.gov/pubmed/18651208
doi: 10.1007/s11095-008-9676-2 URL pmid: 18651208 |
[56] |
Van Eerdenbrugh B, Raina S, Hsieh Y L, Augustijns P , Taylor L S. Pharm. Res., 2014,31(4):969. https://www.ncbi.nlm.nih.gov/pubmed/24271237
doi: 10.1007/s11095-013-1216-z URL pmid: 24271237 |
[57] |
Hsieh Y L, Box K, Taylor L S . J. Pharm. Sci., 2014,103(9):2724. https://www.ncbi.nlm.nih.gov/pubmed/24504566
doi: 10.1002/jps.23890 URL pmid: 24504566 |
[58] |
Hsieh Y L, Ilevbare G A, Van Eerdenbrugh B, Box K J , Sanchez-Felix M V, Taylor L S. Pharm. Res., 2012,29(10):2738. https://www.ncbi.nlm.nih.gov/pubmed/22580905
URL pmid: 22580905 |
[59] |
Bonnett P E, Carpenter K J, Dawson S , Davey R J. Chem. Commun., 2003(6):698.
|
[60] |
Brick M C, Palmer H J, Whitesides T H . Langmuir, 2003,19(16):6367. https://pubs.acs.org/doi/10.1021/la034173o
doi: 10.1021/la034173o URL |
[61] |
Deneau E , Steele G. Org. Process Res. Dev., 2005,9(6):943. https://pubs.acs.org/doi/10.1021/op050107c
doi: 10.1021/op050107c URL |
[62] |
Alonzo D E, Raina S, Zhou D, Gao Y , Zhang G G Z, Taylor L S. Cryst. Growth Des., 2012,12(3):1538. https://pubs.acs.org/doi/10.1021/cg201590j
doi: 10.1021/cg201590j URL |
[63] |
Raina S A , Zhang G G Z, Alonzo D E, Wu J W, Zhu D H, Catron N D, Gao Y, Taylor L S. J. Pharm. Sci., 2014,103(9):2736. https://www.ncbi.nlm.nih.gov/pubmed/24382592
doi: 10.1002/jps.23826 URL pmid: 24382592 |
[64] |
Alonzo D E, Gao Y, Zhou D, Mo H , Zhang G G Z, Taylor L S. J. Pharm. Sci., 2011,100(8):3316. https://www.ncbi.nlm.nih.gov/pubmed/21607951
doi: 10.1002/jps.22579 URL pmid: 21607951 |
[65] |
Konno H, Handa T, Alonzo D E , Taylor L S. Eur. J. Pharm. Biopharm., 2008,70(2):493. https://www.ncbi.nlm.nih.gov/pubmed/18577451
doi: 10.1016/j.ejpb.2008.05.023 URL pmid: 18577451 |
[66] |
Miao L L, Liang Y H, Pan W L, Gou J X, Yin T, Zhang Y, He H B , Tang X. Drug Deliv. Transl. Re., 2019,9(1):344.
|
[67] |
Ilevbare G A, Liu H Y, Pereira J, Edgar K J , Taylor L S. Mol. Pharm., 2013,10(9):3392. https://www.ncbi.nlm.nih.gov/pubmed/23829687
URL pmid: 23829687 |
[68] |
Gao P, Akrami A, Alvarez F, Hu J, Li L, Ma C, Surapaneni S . J. Pharm. Sci., 2009,98(2):516. https://www.ncbi.nlm.nih.gov/pubmed/18543293
URL pmid: 18543293 |
[69] |
Raina S A, Van Eerdenbrugh B, Alonzo D E, Mo HP , Zhang G G Z, Gao Y, Taylor L S. J. Pharm. Sci., 2015,104(6):1981. https://www.ncbi.nlm.nih.gov/pubmed/25808078
doi: 10.1002/jps.24423 URL pmid: 25808078 |
[70] |
Overhoff K A , McConville J T, Yang W, Johnston K P, Peters J I, Williams R O. Pharm. Res., 2008,25(1):167. https://www.ncbi.nlm.nih.gov/pubmed/17968635
doi: 10.1007/s11095-007-9417-y URL pmid: 17968635 |
[71] |
Yeap Y Y, Lock J, Lerkvikarn S, Semin T, Nguyen N, Carrier R L . J. Control. Release, 2019,296: 107. https://www.ncbi.nlm.nih.gov/pubmed/30527813
doi: 10.1016/j.jconrel.2018.11.023 URL pmid: 30527813 |
[72] |
Veesler S, Lafferrere L, Garcia E , Hoff C. Org. Process Res. Dev., 2003,7(6):983. https://pubs.acs.org/doi/10.1021/op034089f
doi: 10.1021/op034089f URL |
[73] |
Groen H, Roberts K J . J. Phys. Chem. B, 2001,105(43):10723.
|
[74] |
Maeda K, Aoyama Y, Fukui K, Hirota S . J. Colloid Interface Sci., 2001,234(1):217. https://www.ncbi.nlm.nih.gov/pubmed/11161508
doi: 10.1006/jcis.2000.7316 URL pmid: 11161508 |
[75] |
Mosquera-Giraldo L I, Taylor L S . Mol. Pharm., 2015,12(2):496.
|
[76] |
Indulkar A S, Box K J, Taylor R, Ruiz R , Taylor L S. Mol. Pharm., 2015,12(7):2365. https://www.ncbi.nlm.nih.gov/pubmed/25984769
URL pmid: 25984769 |
[77] |
Sugihara H , Taylor L S. Mol. Pharm., 2018,15(4):1690. https://www.ncbi.nlm.nih.gov/pubmed/29502424
doi: 10.1021/acs.molpharmaceut.8b00081 URL pmid: 29502424 |
[78] |
Indulkar A S, Gao Y, Raina S A , Zhang G G Z, Taylor L S. Mol. Pharm., 2016,13(6):2059. https://www.ncbi.nlm.nih.gov/pubmed/27138900
URL pmid: 27138900 |
[79] |
Paus R, Ji Y H, Vahle L, Sadowski G . Mol. Pharm., 2015,12(8):2823. https://www.ncbi.nlm.nih.gov/pubmed/26107071
URL pmid: 26107071 |
[80] |
Trasi N S, Taylor L S . J. Pharm. Sci., 2015,104(8):2583.
|
[81] |
Ilevbare G A , Taylor L S. Cryst. Growth Des., 2013,13(4):1497.
|
[82] |
Taylor L S , Zhang G G Z. Adv. Drug Delivery Rev., 2016,101: 122.
|
[83] |
Murdande S B, Pikal M J, Shanker R M, Bogner R H . J. Pharm. Sci., 2010,99(3):1254. https://www.ncbi.nlm.nih.gov/pubmed/19697391
URL pmid: 19697391 |
[84] |
Murdande S B, Pikal M J, Shanker R M , Bogner R H. Pharm. Res., 2010,27(12):2704. https://www.ncbi.nlm.nih.gov/pubmed/20859662
URL pmid: 20859662 |
[85] |
Hoffman J D . J. Chem. Phys., 1958,29(5):1192.
|
[86] |
Lupis C H P . Chemical Thermodynamics of Materials. NY: Elsevier Science Publishing, 1983. 72.
|
[87] |
Lafferrere L, Hoff C , Veesler S. Cryst. Growth Des., 2004,4(6):1175.
|
[88] |
Sakhare S D , Anand V S K, Karan A, Sree K N, Vasantharaju S G, Pai G, Dengale S J. J. Pharm. Innov., 2018. 1.
|
[89] |
Escuder B , Miravet J F. Functional Molecular Gels. Cambridge: Royal Society of Chemistry, 2013. 30.
|
[90] |
Noro A, Hayashi M, Matsushita Y . Soft Matter, 2012,8(24):6416.
|
[91] |
Dudukovic N A, Zukoski C F . Langmuir, 2014,30(15):4493. https://www.ncbi.nlm.nih.gov/pubmed/24684510
doi: 10.1021/la500589f URL pmid: 24684510 |
[92] |
Adams D J, Butler M F, Frith W J, Kirkland M, Mullen L, Sanderson P . Soft Matter, 2009,5(9):1856.
|
[93] |
Tang C, Smith A M, Collins R F, Ulijn R V, Saiani A . Langmuir, 2009,25(16):9447.
|
[94] |
Raeburn J, Cardoso A Z , Adams D J. Chem. Soc. Rev., 2013,42(12):5143.
|
[95] |
Wang Y J, Tang L M , Yu J. Cryst. Growth Des., 2008,8(3):884.
|
[96] |
Estroff L A , Hamilton A D. Chem. Rev., 2004,104(3):1201. https://www.ncbi.nlm.nih.gov/pubmed/15008620
doi: 10.1021/cr0302049 URL pmid: 15008620 |
[97] |
Liu X Y, Sawant P D, Tan W B, Noor I B, Pramesti C, Chen B H . J. Am. Chem. Soc., 2002,124(50):15055. https://www.ncbi.nlm.nih.gov/pubmed/12475350
doi: 10.1021/ja0206137 URL pmid: 12475350 |
[98] |
Liu X Y , Sawant P D. Angew. Chem. Int. Edit. 2002,41(19):3641.
|
[99] |
Roy S, Javid N, Frederix P W, Lamprou D A, Urquhart A J, Hunt N T, Halling P J, Ulijn R V . Chemistry, 2012,18(37):11723. https://www.ncbi.nlm.nih.gov/pubmed/22888053
URL pmid: 22888053 |
[100] |
Liu X Y , Sawant P D. Adv. Mater., 2002,14: 421.
|
[101] |
Lescanne M, Colin A, Mondain-Monval O, Fages F, Pozzo J L . Langmuir, 2003,19: 2013.
|
[102] |
Qiu Y, Park K . Adv. Drug Delivery Rev., 2001,53(3):321.
|
[103] |
Peppas N A, Bures P, Leobandung W , Ichikawa H. Eur. J. Pharm. Biopharm., 2000,50(1):27. https://www.ncbi.nlm.nih.gov/pubmed/10840191
URL pmid: 10840191 |
[104] |
Miyata T, Uragami T, Nakamae K . Adv. Drug Delivery Rev., 2002,54(1):79.
|
[105] |
Pang Z T, Wei Y F, Wang N N, Zhang J J, Gao Y , Qian S. Int. J. Pharm., 2018,548(1):625. https://www.ncbi.nlm.nih.gov/pubmed/30016673
doi: 10.1016/j.ijpharm.2018.07.038 URL pmid: 30016673 |
[106] |
Tsuru K, Ohtsuki C, Osaka A, Iwamoto T, Mackenzie J D . J. Mater. Sci. Mater. Med., 1997,8(3):157. https://www.ncbi.nlm.nih.gov/pubmed/15348769
URL pmid: 15348769 |
[107] |
Xing B, Yu C W, Chow K H, Ho P L, Fu D, Xu B . J. Am. Chem. Soc., 2002,124(50):14846. https://www.ncbi.nlm.nih.gov/pubmed/12475316
doi: 10.1021/ja028539f URL pmid: 12475316 |
[108] |
Nagy Z K, Chew J W, Fujiwara M, Braatz R D . J. Process Control, 2008,18(3/4):399.
|
[109] |
Perepezko J H. Mater. Sci. Eng. A, 1997,226/228: 374.
|
[110] |
Perepezko J H. Mater. Sci. Eng. A, 1994,178(1/2):105. https://linkinghub.elsevier.com/retrieve/pii/0921509394905274
doi: 10.1016/0921-5093(94)90527-4 URL |
[111] |
Bennema P . J. Cryst. Growth, 1967,1(5):278.
|
[112] |
Davey R J, Milisavljevic B , Bourne J R. Phys. Chem., 1988,92(7):2032.
|
[113] |
Bennema P . J. Cryst. Growth, 1967,1(5):287. https://linkinghub.elsevier.com/retrieve/pii/0022024867900358
doi: 10.1016/0022-0248(67)90035-8 URL |
[114] |
Srinivasan K , Sherwood J N. Cryst. Growth Des., 2005,5: 1359.
|
[115] |
Sunagawa I, Sukamoto K, Maiwat K, Onuma K . Prog. Cryst. Growth Charact. Mater., 1995,30: 153.
|
[116] |
Joshi M S, Paul B K . J. Cryst. Growth, 1974,22(4):321. https://linkinghub.elsevier.com/retrieve/pii/0022024874901778
doi: 10.1016/0022-0248(74)90177-8 URL |
[117] |
Liang Z Z, Zhang M, Wu F, Chen J F, Xue C Y , Zhao H. Comput. Chem. Eng., 2017,99: 296. https://linkinghub.elsevier.com/retrieve/pii/S0098135417300108
doi: 10.1016/j.compchemeng.2017.01.010 URL |
[118] |
Kitamura M, Hara T , Takimoto-Kamimura M. Cryst. Growth Des., 2006,6(8):1945. https://pubs.acs.org/doi/10.1021/cg050464e
doi: 10.1021/cg050464e URL |
[119] |
Mattei A, Li T . Pharm. Res., 2012,29(2):460. https://www.ncbi.nlm.nih.gov/pubmed/21879384
doi: 10.1007/s11095-011-0574-7 URL pmid: 21879384 |
[120] |
Dahan A, Miller J M, Hoffman A, Amidon G E, Amidon G L . J. Pharm. Sci., 2010,99(6):2739. https://www.ncbi.nlm.nih.gov/pubmed/20039391
doi: 10.1002/jps.22033 URL pmid: 20039391 |
[121] |
Mellaerts R, Mols R, Kayaert P, Annaert P, Van Humbeeck J , Van den Mooter G, Martens J A, Augustijns P. Int. J. Pharm., 2008,357(1/2):169.
|
[122] |
Kawakami K . Adv. Drug Delivery Rev., 2012,64(6):480.
|
[123] |
Yasuji T, Takeuchi H, Kawashima Y . Adv. Drug Delivery Rev., 2008,60(3):388.
|
[124] |
Li J, Miao X Q, Chen T K, Ouyang D F , Zheng Y. Asian J. Pharm. Sci., 2016,11(4):528.
|
[125] |
Maniruzzaman M, Nair A, Scoutaris N , Bradley M S A, Snowden M J, Douroumis D. Int. J. Pharm., 2015,496(1):42. https://www.ncbi.nlm.nih.gov/pubmed/26403386
URL pmid: 26403386 |
[126] |
Craig D Q M . Int. J. Pharm., 2002,231(2):131. https://www.ncbi.nlm.nih.gov/pubmed/11755266
doi: 10.1016/s0378-5173(01)00891-2 URL pmid: 11755266 |
[127] |
Vasconcelos T, Sarmento B, Costa P . Drug Discov. Today, 2007,12(23/24):1068.
|
[128] |
Angi R, Solymosi T, Erdosi N, Jordan T, Karpati B, Basa-Denes O, Ujhelyi A , McDermott J, Roe C, Mair S, Otvos Z, Molnar L, Glavinas H. AAPS Pharmscitech, 2019,20(2):90. https://www.ncbi.nlm.nih.gov/pubmed/30684094
doi: 10.1208/s12249-018-1270-2 URL pmid: 30684094 |
[129] |
Kim S K, Lee H K, Na Y G, Bang K H, Lee H J, Wang M, Huh H W , Cho C W. Int. J. Pharm., 2019,555: 11. https://www.ncbi.nlm.nih.gov/pubmed/30448313
URL pmid: 30448313 |
[130] |
Huang R, Han J W, Wang R N, Zhao X L, Qiao H Z, Chen L H, Li W, Di L Q, Zhang W , Li J S. Eur. J. Pharm. Sci., 2019,130: 147. https://www.ncbi.nlm.nih.gov/pubmed/30699368
doi: 10.1016/j.ejps.2019.01.031 URL pmid: 30699368 |
[131] |
Lenz E, Lobmann K, Rades T, Knop K, Kleinebudde P . J. Pharm. Sci., 2017,106(1):302. https://www.ncbi.nlm.nih.gov/pubmed/27817830
doi: 10.1016/j.xphs.2016.09.027 URL pmid: 27817830 |
[132] |
Shayanfar A, Ghavimi H, Hamishehkar H, Jouyban A . J. Pharm. Pharm. Sci., 2013,16(4):577. https://www.ncbi.nlm.nih.gov/pubmed/24210065
doi: 10.18433/j3xs4s URL pmid: 24210065 |
[133] |
Shayanfar A, Jouyban A . J. Pharm. Innov., 2013,8(4):218.
|
[134] |
Qian S, Li Z, Heng W L, Liang S J, Ma D, Gao Y, Zhang J J , Wei Y F. RSC Adv., 2016,6(108):106396.
|
[135] |
Dengale S J, Ranjan O P, Hussen S S , Krishna B S M, Musmade P B, Shenoy G G, Bhat K. Eur. J. Pharm. Sci., 2014,62: 57. https://www.ncbi.nlm.nih.gov/pubmed/24878386
doi: 10.1016/j.ejps.2014.05.015 URL pmid: 24878386 |
[136] |
Löbmann K, Laitinen R, Grohganz H, Gordon K C, Strachan C, Rades T . Mol. Pharm., 2011,8(5):1919. https://www.ncbi.nlm.nih.gov/pubmed/21815614
URL pmid: 21815614 |
[137] |
Löbmann K, Strachan C, Grohganz H, Rades T, Korhonen O , Laitinen R. Eur. J. Pharm. Biopharm., 2012,81(1):159. https://www.ncbi.nlm.nih.gov/pubmed/22353489
doi: 10.1016/j.ejpb.2012.02.004 URL pmid: 22353489 |
[138] |
Gniado K, Löbmann K, Rades T , Erxleben A. Int. J. Pharm., 2016,504(1/2):20.
|
[139] |
Lenz E, Jensen K T, Blaabjerg L I, Knop K, Grohganz H, Löbmann K, Rades T , Kleinebudde P. Eur. J. Pharm. Biopharm., 2015,96: 44. https://www.ncbi.nlm.nih.gov/pubmed/26197392
URL pmid: 26197392 |
[140] |
Wei Y F, Zhou S Y, Hao T Y, Zhang J J, Gao Y , Qian S. Eur. J. Pharm., Sci., 2019,129: 21.
|
[141] |
Hirakawa Y, Ueda H, Miyano T, Kamiya N , Goto M. Int. J. Pharm., 2019,569: 118582. https://www.ncbi.nlm.nih.gov/pubmed/31381987
doi: 10.1016/j.ijpharm.2019.118582 URL pmid: 31381987 |
[142] |
Friscic T , Jones W. Cryst. Growth Des., 2009,9(3):1621.
|
[143] |
Padrela L, Rodrigues M A, Velaga S R, Matos H A , De Azevedo E G. Eur. J. Pharm. Sci., 2009,38(1):9. https://www.ncbi.nlm.nih.gov/pubmed/19477273
doi: 10.1016/j.ejps.2009.05.010 URL pmid: 19477273 |
[144] |
Alhalaweh A , Velaga S P. Cryst. Growth Des., 2010,10(8):3302.
|
[145] |
Medina C, Daurio D, Nagapudi K , Alvarez-Nunez F. J. Pharm. Sci., 2010,99(4):1693. https://www.ncbi.nlm.nih.gov/pubmed/19774652
doi: 10.1002/jps.21942 URL pmid: 19774652 |
[146] |
Gao Y, Zu H , Zhang J J. Pharm. Pharmacol., 2011,63(4):483. https://www.ncbi.nlm.nih.gov/pubmed/21401599
doi: 10.1111/j.2042-7158.2010.01246.x URL pmid: 21401599 |
[147] |
Sanphui P, Devi V K, Clara D, Malviya N, Ganguly S , Desiraju G R. Mol. Pharm., 2015,12(5):1615. https://www.ncbi.nlm.nih.gov/pubmed/25800383
doi: 10.1021/acs.molpharmaceut.5b00020 URL pmid: 25800383 |
[148] |
Song Y, Wang L Y, Liu F, Li Y T, Wu Z Y, Yan C W . CrystEngComm, 2019,21(19):3064.
|
[149] |
Seo J W, Hwang K M, Lee S H, Kim D W , Park E S. Pharm. Dev. Technol., 2018,23(9):890. https://www.ncbi.nlm.nih.gov/pubmed/28535125
doi: 10.1080/10837450.2017.1334664 URL pmid: 28535125 |
[150] |
Benjamin E J , Lin L H. Drug Dev. Ind. Pharm., 1985,11(4):771. http://www.tandfonline.com/doi/full/10.3109/03639048509057455
doi: 10.3109/03639048509057455 URL |
[151] |
Morissette S L, Almarsson O, Peterson M L, Remenar J F, Read M J, Lemmo A V, Ellis S, Cima M J, Gardner C R . Adv. Drug Delivery Rev., 2004,56(3):275. https://linkinghub.elsevier.com/retrieve/pii/S0169409X03002187
doi: 10.1016/j.addr.2003.10.020 URL |
[152] |
Kakran M, Shegokar R, Sahoo N G, Shaal L A, Li L , Muller R H. Eur. J. Pharm. Biopharm., 2012,80(1):113. https://www.ncbi.nlm.nih.gov/pubmed/21896330
doi: 10.1016/j.ejpb.2011.08.006 URL pmid: 21896330 |
[153] |
Hintz R J , Johnson K C. Int. J. Pharm., 1989,51: 9. https://linkinghub.elsevier.com/retrieve/pii/0378517389900690
doi: 10.1016/0378-5173(89)90069-0 URL |
[154] |
Muller R H, Keck C M . J. Biotechnol., 2004,113(1/3):151. https://linkinghub.elsevier.com/retrieve/pii/S0168165604003128
doi: 10.1016/j.jbiotec.2004.06.007 URL |
[155] |
Shegokar R , Muller R H. Int. J. Pharm., 2010,399(1/2):129. https://linkinghub.elsevier.com/retrieve/pii/S0378517310005715
doi: 10.1016/j.ijpharm.2010.07.044 URL |
[156] |
Mu H L, Holm R , Mullertz A. Int. J. Pharm., 2013,453(1):215. https://www.ncbi.nlm.nih.gov/pubmed/23578826
doi: 10.1016/j.ijpharm.2013.03.054 URL pmid: 23578826 |
[157] |
Lee D H, Yeom D W, Song Y S, Cho H R, Choi Y S, Kong M J , Choi Y W. Int. J. Pharm., 2015,478(1):341. https://www.ncbi.nlm.nih.gov/pubmed/25437113
doi: 10.1016/j.ijpharm.2014.11.060 URL pmid: 25437113 |
[158] |
Kapoor M , Siegel R A. Mol. Pharm., 2013,10(9):3519. https://www.ncbi.nlm.nih.gov/pubmed/23937162
doi: 10.1021/mp400272m URL pmid: 23937162 |
[159] |
Qian S, Li C R, Zuo Z . Curr. Drug MeTab., 2012,13(4):372. 81c405ce-ea60-4a07-8218-02986eed1c29WOS:000302951700005
|
[160] |
Fong S Y K, Bauer-Brandl A, Brandl M . Expert Opin. Drug Deliv., 2017,14(3):403. https://www.ncbi.nlm.nih.gov/pubmed/27488049
doi: 10.1080/17425247.2016.1218465 URL pmid: 27488049 |
[161] |
Kuentz M . Adv. Drug Delivery Rev., 2018,142: 50. https://linkinghub.elsevier.com/retrieve/pii/S0169409X18302904
doi: 10.1016/j.addr.2018.11.003 URL |
[162] |
Wyttenbach N , Kuentz M. Eur. J. Pharm. Biopharm., 2017,112: 204. https://www.ncbi.nlm.nih.gov/pubmed/27903457
doi: 10.1016/j.ejpb.2016.11.031 URL pmid: 27903457 |
[163] |
Sarnes A, Kovalainen M, Hakkinen M R, Laaksonen T, Laru J, Kiesvaara J, Ilkka J, Oksala O, Ronkko S, Jarvinen K, Hirvonen J, Peltonen L . J. Control Release, 2014,180: 109. https://www.ncbi.nlm.nih.gov/pubmed/24566254
doi: 10.1016/j.jconrel.2014.02.016 URL pmid: 24566254 |
[164] |
Demuth B, Nagy Z K, Balogh A, Vigh T, Marosi G, Verreck G, Van Assche I , Brewster M E. Int. J. Pharm., 2015,486(1/2):268. https://linkinghub.elsevier.com/retrieve/pii/S0378517315002690
doi: 10.1016/j.ijpharm.2015.03.053 URL |
[165] |
Stewart A M, Grass M E, Brodeur T J, Goodwin A K, Morgen M M, Friesen D T , Vodak D T. Mol. Pharm., 2017,14(7):2437. https://www.ncbi.nlm.nih.gov/pubmed/28591516
doi: 10.1021/acs.molpharmaceut.7b00338 URL pmid: 28591516 |
[166] |
Iwashita M, Hashizume K, Umehara M, Ishigami T, Onishi S, Yamamoto M, Higashi K , Moribe K. Int. J. Pharm., 2019,558: 215. https://www.ncbi.nlm.nih.gov/pubmed/30654059
doi: 10.1016/j.ijpharm.2018.12.092 URL pmid: 30654059 |
[167] |
Bohr A, Nascimento T L, Harmankaya N, Weisser J J, Wang Y Y, Grohganz H, Rades T, Löbmann K . Molecules, 2019,24(2):266. http://www.mdpi.com/1420-3049/24/2/266
doi: 10.3390/molecules24020266 URL |
[168] |
Petry I, Löbmann K, Grohganz H, Rades T , Leopold C S. Int. J. Pharm., 2019,558: 357. https://www.ncbi.nlm.nih.gov/pubmed/30641182
doi: 10.1016/j.ijpharm.2018.12.091 URL pmid: 30641182 |
[169] |
Kavanagh O N, Croker D M, Walker G M , Zaworotko M J. Drug Discov. Today, 2019,24(3):796. https://www.ncbi.nlm.nih.gov/pubmed/30521935
doi: 10.1016/j.drudis.2018.11.023 URL pmid: 30521935 |
[170] |
Thakuria R, Sarma B . Crystals, 2018,8(2):101. http://www.mdpi.com/2073-4352/8/2/101
doi: 10.3390/cryst8020101 URL |
[171] |
Suzuki Y, Muangnoi C, Thaweesest W, Teerawonganan P , Ratnatilaka Na Bhuket P, Titapiwatanakun V, Yoshimura-Fujii M, Sritularak B, Likhitwitayawuid K, Rojsitthisak P, Fukami T. Biol. Pharm. Bull., 2019,42(6):1004. https://www.ncbi.nlm.nih.gov/pubmed/31155574
doi: 10.1248/bpb.b19-00048 URL pmid: 31155574 |
[172] |
Nolan S F , Roman M W. Issues Ment. Health Nurs., 2012,33(5):342. https://www.ncbi.nlm.nih.gov/pubmed/22545643
doi: 10.3109/01612840.2012.669025 URL pmid: 22545643 |
[173] |
Valentine W J, Godwin V I, Osborne D A, Liu J, Fujiwara Y, Van Brocklyn J, Bittman R, Parrill A L, Tigyi G . J. Biol. Chem., 2011,286(35):30513. https://www.ncbi.nlm.nih.gov/pubmed/21719706
doi: 10.1074/jbc.M111.263442 URL pmid: 21719706 |
[174] |
Yue P F, Liu Y, Xie J, Chen Y C, Yang M . Acta Pharm. Sin. B, 2018,53: 539.
|
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