Improving hygroscopic stability of palmatine chloride by forming a pharmaceutical salt cocrystal of palmatine chloride-gallic acid with neutral molecule

Zhang, Yunan; Li, Yujiao; Chang, Liang; Liu, Lixin; Feng, Yanru; Wu, Lili; Zhang, Lei

doi:10.1016/j.jddst.2021.102839

Cited by 5 publications

(6 citation statements)

References 24 publications

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“…Although the novel salt form exhibited low hygroscopicity, the solubility of the salt form was reduced [ 19 ]. A similar observation was noted with the palmatine saccharinate salt and gallic acid-palmatine chloride co-crystal, which showed better hygroscopic stability but reduced its aqueous solubility [ 23 , 35 ]. Another study by Ribeiro et al [ 15 ] aimed at reducing the hygroscopicity of adiphenine hydrochloride by preparing more stable oxalate and citrate salt forms.…”

Section: Moisture Interaction With Solidsupporting

confidence: 70%

“…The following examples support the aforesaid statement. Berberine chloride (BCl) and palmatine chloride are the major alkaloidal compounds used in herbal preparations [ 16 , 23 , 35 , 40 ]. The hydrochloride salt forms of both compounds are hygroscopic but their other salt forms and co-crystals are relatively less hygroscopic in nature.…”

Section: Moisture Interaction With Solidmentioning

confidence: 99%

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Co-Crystallization Approach to Enhance the Stability of Moisture-Sensitive Drugs

et al. 2023

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Stability is an essential quality attribute of any pharmaceutical formulation. Poor stability can change the color and physical appearance of a drug, directly impacting the patient’s perception. Unstable drug products may also face loss of active pharmaceutical ingredients (APIs) and degradation, making the medicine ineffective and toxic. Moisture content is known to be the leading cause of the degradation of nearly 50% of medicinal products, leading to impurities in solid dose formulations. The polarity of the atoms in an API and the surface chemistry of API particles majorly influence the affinity towards water molecules. Moisture induces chemical reactions, including free water that has also been identified as an important factor in determining drug product stability. Among the various approaches, crystal engineering and specifically co-crystals, have a proven ability to increase the stability of moisture-sensitive APIs. Other approaches, such as changing the salt form, can lead to solubility issues, thus making the co-crystal approach more suited to enhancing hygroscopic stability. There are many reported studies where co-crystals have exhibited reduced hygroscopicity compared to pure API, thereby improving the product’s stability. In this review, the authors focus on recent updates and trends in these studies related to improving the hygroscopic stability of compounds, discuss the reasons behind the enhanced stability, and briefly discuss the screening of co-formers for moisture-sensitive drugs.

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Section: Moisture Interaction With Solidsupporting

confidence: 70%

Section: Moisture Interaction With Solidmentioning

confidence: 99%

Co-Crystallization Approach to Enhance the Stability of Moisture-Sensitive Drugs

et al. 2023

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“…On the other hand, the multicomponent crystal systems comprise drug molecules that have different intermolecular interactions with other molecules (guest molecule or coformer) or ion, resulting in the formation of a new solid form without alterations in the covalent chemistry [7,14,15]. This group is formed by solvates, hydrates, co-crystals, salts, and a combination of these (like salt hydrates, salt solvates, co-crystal solvates, co-crystal salt, and co-crystal salt solvates) [14,[16][17][18][19][20]. In addition, each multi-component system may have polymorphs [21].…”

Section: Solid Forms Of Pharmaceutical Crystalsmentioning

confidence: 99%

“…ssNMR is a non-destructive and multinuclear technique that exploits the magnetic properties of certain nuclei, for example, 1 H, 13 C, 15 N, 17 O, and 19 F. Although it is a non-routinary expensive methodology that has extensive experimental times and robust expertise users are required, it is widely used in pharmaceutical applications [32].…”

Section: Solid State Nuclear Magnetic Resonance (Ssnmr)mentioning

confidence: 99%

Pharmaceutical Crystals: Development, Optimization, Characterization and Biopharmaceutical Aspects

Bongioanni¹,

Bueno²,

Mezzano³

et al. 2023

Crystal Growth and Chirality - Technologies and Applications

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In the solid state, the active pharmaceutical ingredients tend to exhibit crystalline order. In this regard, the interest in the crystalline solid state has expanded to include single-component compounds as well as multicomponent systems such as salts, hydrates, solvates, and co-crystals. The study of crystalline behavior is recognized as an essential component of preformulation research in pharmaceutical sciences and industries. The crystalline form can impact the drug properties such as solubility, dissolution rate, stability, hygroscopicity, and toxicity profile. Therefore, each solid form must be appropriately identified and characterized because it will affect the drug formulation, including the pharmacokinetic, pharmacodynamic, and safety properties of the formulation. In this context, this chapter will cover topics such as synthesis approaches (including nucleation and crystallization procedures), crystal polymorphism, solid state characterization techniques and the impact of crystals on physicochemical and biopharmaceutical properties.

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“…In addition, palmatine chloride, which has antidepressant, pain-relieving, sedative, anti-inflammatory, antifungal, and antibacterial properties, was co-crystallized with co-former gallic acid (GaA). The resultant cocrystals exhibited considerable reduction in hygroscopicity, as GA molecule and methanol inserted themselves tightly into binding sites between chloride anions and ambient water molecules during the self-assembly of cocrystals, hence decreasing the binding ability of the cocrystal with environmental moisture [ 97 ]…”

Section: Formulation Strategies To Reduce or Control Hygroscopicitymentioning

confidence: 99%

Formulation Strategies to Improve the Stability and Handling of Oral Solid Dosage Forms of Highly Hygroscopic Pharmaceuticals and Nutraceuticals

Ling

Hadinoto

2022

Pharmaceutics

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Highly hygroscopic pharmaceutical and nutraceutical solids are prone to significant changes in their physicochemical properties due to chemical degradation and/or solid-state transition, resulting in adverse effects on their therapeutic performances and shelf life. Moisture absorption also leads to excessive wetting of the solids, causing their difficult handling during manufacturing. In this review, four formulation strategies that have been employed to tackle hygroscopicity issues in oral solid dosage forms of pharmaceuticals/nutraceuticals were discussed. The four strategies are (1) film coating, (2) encapsulation by spray drying or coacervation, (3) co-processing with excipients, and (4) crystal engineering by co-crystallization. Film coating and encapsulation work by acting as barriers between the hygroscopic active ingredients in the core and the environment, whereas co-processing with excipients works mainly by adding excipients that deflect moisture away from the active ingredients. Co-crystallization works by altering the crystal packing arrangements by introducing stabilizing co-formers. For hygroscopic pharmaceuticals, coating and co-crystallization are the most commonly employed strategies, whereas coating and encapsulation are popular for hygroscopic nutraceuticals (e.g., medicinal herbs, protein hydrolysates). Encapsulation is rarely applied on hygroscopic pharmaceuticals, just as co-crystallization is rarely used for hygroscopic nutraceuticals. Therefore, there is potential for improved hygroscopicity reduction by exploring beyond the traditionally used strategy.

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Improving hygroscopic stability of palmatine chloride by forming a pharmaceutical salt cocrystal of palmatine chloride-gallic acid with neutral molecule

Cited by 5 publications

References 24 publications

Co-Crystallization Approach to Enhance the Stability of Moisture-Sensitive Drugs

Co-Crystallization Approach to Enhance the Stability of Moisture-Sensitive Drugs

Pharmaceutical Crystals: Development, Optimization, Characterization and Biopharmaceutical Aspects

Formulation Strategies to Improve the Stability and Handling of Oral Solid Dosage Forms of Highly Hygroscopic Pharmaceuticals and Nutraceuticals

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