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Progress in Chemistry 2021, Vol. 33 Issue (11): 2116-2127 DOI: 10.7536/PC200943 Previous Articles   Next Articles

• Review •

Crystallization of Amorphous Drugs and Inhibiting Strategies

Minqian Luo1, Weili Heng2, Juan Dai1, Yuanfeng Wei2, Yuan Gao2, 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: Revised: Online: Published:
  • Contact: Jianjun Zhang
  • Supported by:
    National Natural Science Foundation of China(81703712); National Natural Science Foundation of China(81773675); National Natural Science Foundation of China(81873012); “Double First-Class”University Project(CPU2018GY11); “Double First-Class”University Project(CPU2018GY27)
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In comparison to the crystalline forms, amorphous drugs exhibit higher surface free energy, higher apparent solubility and faster dissolution rate. However, since the amorphous state is thermodynamically unstable, amorphous solids tend to transform into their stable crystalline forms, resulting in the decreased dissolution and hence low bioavailability. This paper reviews the fundamental introduction of amorphous drugs, the crystallization theory, the influence factors on the physical stability and strategies for their crystallization inhibition, in order to provide a theoretical guidance for the rational design of amorphous drug products and efficient development of amorphous formulations. All of these could contribute to more applications of amorphous drugs in overcoming the poor water solubility issues.

Contents:

1 Introduction

2 Overview of amorphous drugs

3 Crystallization of amorphous drugs

3.1 Crystallization behaviors of amorphous drugs

3.2 Crystallization tendency of amorphous drugs

3.3 Crystallization theory

4 Influence factors on crystallization of amorphous drugs

4.1 Thermodynamic factors

4.2 Kinetic factors

4.3 Intermolecular interactions

4.4 Water vapor sorption

4.5 Formulation preparation

5 Strategies to inhibit crystallization of amorphous drugs

5.1 To store under low temperatures

5.2 To form amorphous solid dispersions

5.3 To form coamorphous formulations

5.4 To optimize formulation preparation

5.5 Others

6 Conclusion and outlook

Key words: amorphous, dissolution, crystallization, influence factors, crystallization inhibition
Table 1 Comparison for physicochemical properties of amorphous and crystalline solids
Physicochemical properties Amorphous solids Crystalline solids
Birefringence No birefringence Birefringence phenomenon
X-ray pattern A broad diffraction halo Characteristic diffraction peaks
Thermal behavior A glass transition temperature A melting temperature
Surface free energy High Low
Apparent solubility High Low
Dissolution rate Fast Slow
Moisture absorption High Low
Physical stability Poor Great
Compressibility Great Poor
Fig. 1 Enthalpy-temperature diagram of solid drugs(Tm is the melting point and Tg is the glass transition temperature. Below Tg, the “virtual state” defined by the continuation of the supercooled liquid line is the “equilibrium glassy state”, representing the glassy state that is in structural equilibrium.)
Fig. 2 Schematic diagram of several common dissolution behaviors of amorphous drugs and crystalline drugs[24]
Fig. 3 Schematic representation of the classification system of the crystallization tendency determined from heat/cool cycles of the DSC measurement[26]
Fig. 4 Schematic representation of energetics associated with nucleation and crystal growth from the amorphous state
Fig. 5 Schematic representation of time dependence of nucleation I(jc, t):(1) steady state nucleation rate;(2) transient nucleation rate(as per Eq.(5))[11]
Fig. 6 Schematic representation of crystal nucleation and growth rates as a function of temperature[14]
Fig. 7 Schematic plot showing the effect of heat of fusion on the predictions of the Hoffmann equation.(Squares, diamonds, and triangles represent the calculated free energy values for compounds with 55 J/gm, 110 J/gm, and 220 J/gm as heat of fusion, respectively. The melting point used in the above calculations was 433 K.)[11]
Fig. 8 Variation of the relaxation time parameter, τ, with scaled temperature Tg - T. ▲ Sucrose, ■ Indomethacin, ● PVP. Lines indicate the range of values observed.[78]
Fig. 9 Schematic representation of energy of amorphous drugs, crystalline drugs and amorphous solid dispersions
Fig. 10 Schematic representation of stabilization mechanisms of coamorphous systems
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