Crystal growth of progesterone metastable and stable polymorphs by polymer induced herteronucleation (PIHn) method

Araya-Sibaja, Andrea Mariela; Soldi, Valdir; Campos, Carlos Eduardo Maduro de; Cardoso, Simone Gonçalves; Cuffini, Silvia Lucía

doi:10.1002/crat.201500145

Cited by 10 publications

(7 citation statements)

References 20 publications

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“…8,9 For many years, it has been relevant to understand and control the behaviour of steroidal derivatives not only in the liquid phase but also in the solid state. [10][11][12][13][14] It is well known that in organic molecular crystals, the structures are governed by weak intermolecular forces forming well-organized and oriented systems. 15 In fact, the crystalline state presents many advantages for the design of functional materials.…”

Section: Introductionmentioning

confidence: 99%

Designed synthesis of “L” shaped 17-halo-aryl-ethynyl steroids

et al. 2016

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Thirteen steroidal derivatives were synthesized through a Sonogashira cross-coupling reaction which has been found to be an excellent synthetic strategy to introduce halo-aromatic groups into C-17-ethynyl substituted steroidal frameworks. The structural modification was performed on ethynylestradiol, mestranol, norethisterone, ethisterone and 3-ethynyl-3-epi-sarsasapogenin. The solid state study by X-ray diffraction showed that most of them belong to the orthorhombic P2 1 2 1 2 1 space group and the whole family has an "L" conformation, regardless of the nature of the steroid A-ring (3-hydroxy-aromatic or 3-oxo). Due to the presence of several moieties which are susceptible to forming secondary interactions, the crystalline packing is governed by O-H⋯O, C-H⋯O, and C-H⋯π interactions, and only 17α-(4′-iodophenylethynyl)-3-methoxy-estra-1,3,5(10)-trien-17-β-ol (mestranol derivative 3) showed an iodine-iodine interaction (d I⋯I = 4.116 Å). The crystalline packing for ethynylestradiol derivatives 1, 2 and 4 showed the formation of holes with diameters greater than 5.2 Å suggesting their potential application in host guest chemistry or as porous materials.

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Section: Introductionmentioning

confidence: 99%

Designed synthesis of “L” shaped 17-halo-aryl-ethynyl steroids

et al. 2016

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“…at higher supersaturation in the presence of polymeric heteronucleants (Araya-Sibaja et al, 2016). The metastable α-polymorph of indomethacin was also found to crystallize selectively on the layered cellulose nanocrystals generated by dip coating (Lu et al, 2016).…”

Section: Cuffini Et Al Elucidated the Crystallization Of Form II Of mentioning

confidence: 91%

“…Form II is metastable one with 2x solubility advantage. Cuffini et al elucidated the crystallization of form II of progesterone at higher supersaturation in the presence of polymeric heteronucleants (Araya‐Sibaja et al, ). The metastable α‐polymorph of indomethacin was also found to crystallize selectively on the layered cellulose nanocrystals generated by dip coating (Lu et al, ).…”

Section: Pharmaceutical Applicationsmentioning

confidence: 99%

“…Slow-solvent evaporation was one of the most common processes used for demonstration of heteronuclear crystallization (Araya-Sibaja et al, 2016;Curcio et al, 2014;Park et al, 2016;Shi et al, 2013). The process involves the generation of undersaturated solution, where driving force for crystallization was generated by slow-removal of the solvent from the system.…”

Section: Experimental Techniques For Heteronuclear Crystallizationmentioning

confidence: 99%

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Emerging role of primary heterogeneous nucleation in pharmaceutical crystallization

Thakore

Sood

Bansal

2019

Drug Development Research

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Crystallization is an important and difficult to control unit operation in the pharmaceutical industry. Crystallization can control molecular (i.e., polymorphism) and particulate (i.e., particle size and crystal habit) properties of active pharmaceutical ingredient (API). Moreover, these molecular and particulate properties govern the manufacturability, stability, and biopharmaceutical performance of the API and drug product. Nucleation is a key step and primary heterogeneous nucleation is a common mode of nucleation during crystallization. Hence, it is important to understand the parameters affecting primary heterogeneous nucleation, to achieve desirable properties in crystalline APIs. Primary heterogeneous crystallization has usually been linked to the surface characteristics like topography and functionality of the heteronucleant. The review outlines recent findings in the primary heterogeneous crystallization with specific emphasis on its pharmaceutical applications including regulatory considerations. Molecular‐level mechanisms governing heteronucleation and subsequent outcome in terms of molecular as well as particulate‐level properties of API have also been discussed. Moreover, general guidance for the selection of heteronucleant has also been included. Heterogeneous crystallization is a promising tool for efficient crystallization of API having properties for optimal pharmaceutical performance.

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“…Determination of distinct crystal habits is significantly influenced by solvent recrystallization because the morphology depends on the solute–solvent interaction on various crystal faces [ 2 , 3 , 4 ]. Drug crystallization methods include solution crystallization from single or mixed solvents [ 5 , 6 , 7 ], supercritical fluids crystallization [ 8 ], seeding strategies [ 9 ], capillary crystallization [ 10 ], polymer-induced heteronucleation [ 11 ], heteronucleation on substrates [ 12 ], and laser-induced nucleation [ 13 ]. Solution crystallization is one of the most popular methods in drug crystallization.…”

Section: Introductionmentioning

confidence: 99%

Enhanced Water Solubility and Oral Bioavailability of Paclitaxel Crystal Powders through an Innovative Antisolvent Precipitation Process: Antisolvent Crystallization Using Ionic Liquids as Solvent

Yang

et al. 2020

Pharmaceutics

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Paclitaxel (PTX) is a poor water-soluble antineoplastic drug with significant antitumor activity. However, its low bioavailability is a major obstacle for its biomedical applications. Thus, this experiment is designed to prepare PTX crystal powders through an antisolvent precipitation process using 1-hexyl-3-methylimidazolium bromide (HMImBr) as solvent and water as an antisolvent. The factors influencing saturation solubility of PTX crystal powders in water in water were optimized using a single-factor design. The optimum conditions for the antisolvent precipitation process were as follows: 50 mg/mL concentration of the PTX solution, 25 °C temperature, and 1:7 solvent-to-antisolvent ratio. The PTX crystal powders were characterized via scanning electron microscopy, Fourier transform infrared spectroscopy, high-performance liquid chromatography–mass spectrometry, X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, Raman spectroscopy, solid-state nuclear magnetic resonance, and dissolution and oral bioavailability studies. Results showed that the chemical structure of PTX crystal powders were unchanged; however, precipitation of the crystalline structure changed. The dissolution test showed that the dissolution rate and solubility of PTX crystal powders were nearly 3.21-folds higher compared to raw PTX in water, and 1.27 times higher in artificial gastric juice. Meanwhile, the bioavailability of PTX crystal increased 10.88 times than raw PTX. These results suggested that PTX crystal powders might have potential value to become a new oral PTX formulation with high bioavailability.

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Crystal growth of progesterone metastable and stable polymorphs by polymer induced herteronucleation (PIHn) method

Cited by 10 publications

References 20 publications

Designed synthesis of “L” shaped 17-halo-aryl-ethynyl steroids

Designed synthesis of “L” shaped 17-halo-aryl-ethynyl steroids

Emerging role of primary heterogeneous nucleation in pharmaceutical crystallization

Enhanced Water Solubility and Oral Bioavailability of Paclitaxel Crystal Powders through an Innovative Antisolvent Precipitation Process: Antisolvent Crystallization Using Ionic Liquids as Solvent

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