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化学进展 2020, Vol. 32 Issue (6): 698-712 DOI: 10.7536/PC190942 前一篇   后一篇

• 综述与评论 •

过饱和度理论及过饱和药物递送系统

薛一凡1, 孟文卉1, 汪润泽2, 任俊杰1, 衡伟利1, 张建军1,**()   

  1. 1. 中国药科大学药学院 南京 211198
    2. 中国药科大学中药学院 南京 211198
  • 收稿日期:2019-10-09 修回日期:2020-01-13 出版日期:2020-06-05 发布日期:2020-07-06
  • 通讯作者: 张建军
  • 作者简介:
    ** Corresponding author e-mail:
  • 基金资助:
    国家自然科学基金项目(81703712, 81773675, 81873012); “双一流”高校建设项目(CPU2018GY11, CPU2018GY27)

Supersaturation Theory and Supersaturating Drug Delivery System(SDDS)

Yifan Xue1, Wenhui Meng1, Runze Wang2, Junjie Ren1, Weili Heng1, Jianjun Zhang1,**()   

  1. 1. School of Pharmacy, China Pharmaceutical University, Nanjing 211198, China
    2. School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 211198, China
  • Received:2019-10-09 Revised:2020-01-13 Online:2020-06-05 Published:2020-07-06
  • Contact: Jianjun Zhang
  • Supported by:
    the National Natural Science Foundation of China(81703712, 81773675, 81873012); the “Double First-Class” University Project(CPU2018GY11, CPU2018GY27)

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。

In drug research and development, it is a big challenge to effectively improve the solubility/dissolution and in vivo absorption of poorly water-soluble drugs. Currently, supersaturating drug delivery system(SDDS), taking advantage of the drug solution in a supersaturated state, can simultaneously improve the apparent solubility and permeability of drugs. The current article systematically reviews the theory of supersaturation and its application, including generation and maintenance of supersaturation, and the relationship with in vivo drug absorption. Commonly used approaches, especially amorphous solid dispersion, co-crystal, amorphous/co-amorphous systems, have been introduced.

Contents

1 Introduction
2 Synopsis of supersaturation 2.1 Generation2.2 Maintenance2.3 Stability2.4 The relationship between supersaturation and in vivo drug absorption
3 Supersaturating drug delivery system(SDDS) 3.1 Amorphous solid dispersion3.2 Co-amorphous3.3 Co-crystal3.4 Salts3.5 Nanocrystal3.6 Others
4 Conclusion and outlook
()
图1 药物过饱和溶液的“弹簧-降落伞”模型示意图
Fig. 1 Schematic drug concentration-time profiles illustrating the spring and parachute approach of supersaturated solutions
图2 结晶抑制剂对过饱和溶液影响的示意图(以聚合物为例)
Fig. 2 Schematic diagram of the influence of crystallization inhibitors on supersaturated solutions(illustrated by the example of polymer)
图3 温度-药物溶液组成相图(L1:药物晶体溶解度;L2:药物无定形溶解度;L3:富药相中药物浓度)[79]
Fig. 3 Schematic temperature-composition phase diagram of an API in water.(L1: solubility of crystalline drug; L2: solubility of amorphous drug; L3: drug concentration in drug-rich phase.) [79]
图4 均相溶液中混合自由能-组分相图[86]
Fig. 4 Free energy of mixing versus composition diagram in a homogeneous solution[86]
图5 两种具有混溶间隙的液体的混合自由能函数[61]
Fig. 5 Free energy function of mixing for two liquids with a miscibility gap[61]
图6 四项变量-时间曲线(图a包括富药相中药物浓度/药物活度/药物膜通量-时间变化曲线;图b为药物吸收百分比-时间变化曲线)[82]
Fig. 6 Four variables-time schematic diagrams(figure a contains drug concentration in drug-rich phase/activity of drug/flux-time curve; figure b is the percentage of drug absorption-time curve)[82]
图7 常用的药物过饱和递送系统类型
Fig. 7 Common types of supersaturating drug delivery system(SDDS)
表1 部分药物过饱和递送系统(SDDS)的例子
Table 1 Part of examples of Supersaturating Drug Delivery Systems(SDDS)
Drug BCS Trade Name Preparation Method Carrier or Coformer or CCF or Acid/Base ref
Amorphous
Cefuroxime Axetil Ceftin? 162
Nelfinavir Mesylate Viracept? 162
Rosuvastatin Calcium Crestor? 162
Quinapril Hydrochloride Accupril? 162
Zafirlukast Accolate? 162
ASD
Itraconazole Sporanox? Spray-drying HPMC 163
Lopinavir、Ritonavir Kaletra? Melt-extrusion PVPVA64 164
Ritonavir Norvir? Melt-extrusion PVPVA64 164
Griseofulvin Gris-PEG? Melt-extrusion PEG 164
Fenofibrate Fenoglide? Spray-extrusion PEG 164
Everolimus Certican? Spray-drying HPMC 164
Etravirine Intelence? Spray-drying HPMC 162
Celecoxib Spray-drying PVP and SDS 128
Itraconazole Spray-drying HPMC-AS 165
Ticagrelor Solvent Evaporation TPGS and Neusilin? US2 129
Curcumin Co-milling Chitosan Oligosaccharide 130
Nobiletin Hot-melt Extrusion Methyl Hesperidin 166
Co-amorphous
Docetaxel Rotary Vacuum Evaporation Myricetin 140
Docetaxel Vibrational Ball Milling Bicalutamide 167
Carvedilol Spray-drying Aspartic Acid 168
Lurasidone Hydrochloride Rotary Vacuum Evaporation Saccharin 50
Indomethacin Hot-melt Extrusion and Spray-drying Arginine and Copovidone 131
Atorvastatin Calcium Solvent Evaporation Nicotinamide 132
Lurasidone Hydrochloride Solvent Evaporation Repaglinide 134
Atorvastatin Calcium Solvent Evaporation Carvedilol 133
Ritonavir Solvent Evaporation Indomethacin 135
Co-crystal
Valsartan Entresto? Sacubitril 169
Ipragliflozin Suglat? L-proline 169
Sodium Valproate Epilim? Valproic Acid 170
Ketoconazole Slow Solvent Evaporation Fumaric Acid 54
Oxyresveratrol Balls Milling Citric Acid 171
Acetazolamide Grinding and Solvent-Evaporation Proline 148
Hydrochlorothiazide Grinding Nicotinamide 147
Crystal salts
Lurasidone Hydrochloride Latuda? 172
Fingolimod Hydrochloride Gilenya? 173
Ketoconazole Slow Solvent Evaporation Oxalate Acid 54
Celecoxib Slow Solvent Evaporation Sodium Hydroxide 29
Nanocrystal
Aprepitant Emend? Wet Media Milling 174
Sirolimus Rapamune? Wet Media Milling 174
Fenofibrate TriCor? Wet Media Milling 174
Megestrol Acetate Megace ES? Wet Media Milling 174
Itraconazole Rapid Wet Milling 163
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