Process‐Induced Phase Transformation of Berberine Chloride Hydrates

Tong, Henry H.Y.; Chow, Aviva S.F.; Chan, H.M.; Chow, Albert H.L.; Wan, Yetta K.Y.; Williams, Ian D.; Shek, Fanny L. Y.; Chan, Chak Keung

doi:10.1002/jps.21983

Cited by 42 publications

(19 citation statements)

References 16 publications

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“…For any crystal form in general, and the hydration/dehydration processes of hydrates in particular, processes can be studied either by varying the temperature (variable temperature or temperature controlled PXRD) or the humidity (humidity controlled PXRD). Temperature resolved PXRD is more commonly used [62], e.g., for the characterisation of berberine hydrochloride hydrates [63]. The authors show that the dihydrate dehydrates to the anhydrate in the range from 60 to 70 °C, while the tetrahydrate dehydrates to the dihydrate between 25 and 30 °C.…”

Section: Powder X-ray Diffractionmentioning

confidence: 99%

X-ray and Neutron Diffraction in the Study of Organic Crystalline Hydrates

Fucke

Steed

2010

Water

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A review. Diffraction methods are a powerful tool to investigate the crystal structure of organic compounds in general and their hydrates in particular. The laboratory standard technique of single crystal X-ray diffraction gives information about the molecular conformation, packing and hydrogen bonding in the crystal structure, while powder X-ray diffraction on bulk material can trace hydration/dehydration processes and phase transitions under non-ambient conditions. Neutron diffraction is a valuable complementary technique to X-ray diffraction and gives highly accurate hydrogen atom positions due to the interaction of the radiation with the atomic nuclei.Although not yet often applied to organic hydrates, neutron single crystal and neutron powder diffraction give precise structural data on hydrogen bonding networks which will help explain why hydrates form in the first place.

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Section: Powder X-ray Diffractionmentioning

confidence: 99%

X-ray and Neutron Diffraction in the Study of Organic Crystalline Hydrates

Fucke

Steed

2010

Water

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“…Surprisingly, while the structure of berberine crystallized with a variety of counter-anions has been reported (Moniot & Shamma, 1979; Abadi et al , 1984; Kariuki & Jones, 1995; Marek, Sečkářová et al , 2003; Tong et al , 2010; Chahine et al , 2011), as have the structures of an assortment of 8-substituted derivatives of dihydroberberine (Man et al , 2001; Marek, Hulová et al , 2003; Dostál et al , 2004; Maier et al , 2010; Man et al , 2011), a determination of the crystal structure of dihydroberberine itself has not been undertaken. Herein, we report its crystal structure from X-ray diffraction data at 150 K.…”

Section: Introductionmentioning

confidence: 99%

Weak C—H...X(X= O, N) hydrogen bonds in the crystal structure of dihydroberberine

2014

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Dihydroberberine (systematic name: 9,10-dimethoxy-6,8-dihydro-5H-1,3-dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline), C20H19NO4, a reduced form of pharmacologically important berberine, crystallizes from ethanol without interstitial solvent. The molecule shows a dihedral angle of 27.94 (5)° between the two arene rings at the ends of the molecule, owing to the partial saturation of the inner quinolizine ring system. Although lacking classical O—H or N—H donors, the packing in the crystalline state is clearly governed by C—H···N and C—H···O hydrogen bonds involving the two acetal-type C—H bonds of the 1,3-dioxole ring. Each dihydroberberine molecule is engaged in four hydrogen bonds with neighbouring molecules, twice as donor and twice as acceptor, thus forming a two-dimensional sheet network that lies parallel to the (100) plane.

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“…A key consideration is the potential for change of the solid form (phase transformation) during drug product processing. There are many cases documented in the pharmaceutical literature of where the crystal form of the API has been changed during drug product processing [106,107,108]. To understand this risk, it is recommended to map out the range of conditions (e.g.…”

Section: Solid Form and Particle Properties Of The Api After Drug Promentioning

confidence: 99%

“…There are many cases documented in the pharmaceutical literature of where the crystal form of the API has been changed during drug product processing. [106,107,108] To understand this risk, it is recommended to map out the range of conditions (e.g. temperature, pressure, water activity and composition) that the API is exposed to during processing.…”

Section: Solid Form and Particle Properties Of The Api After Drug Promentioning

confidence: 99%

Integration of active pharmaceutical ingredient solid form selection and particle engineering into drug product design

Ticehurst

Marziano

2015

Journal of Pharmacy and Pharmacology

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This review seeks to offer a broad perspective that encompasses an understanding of the drug product attributes affected by active pharmaceutical ingredient (API) physical properties, their link to solid form selection and the role of particle engineering. While the crucial role of active pharmaceutical ingredient (API) solid form selection is universally acknowledged in the pharmaceutical industry, the value of increasing effort to understanding the link between solid form, API physical properties and drug product formulation and manufacture is now also being recognised.A truly holistic strategy for drug product development should focus on connecting solid form selection, particle engineering and formulation design to both exploit opportunities to access simpler manufacturing operations and prevent failures. Modelling and predictive tools that assist in establishing these links early in product development are discussed. In addition, the potential for differences between the ingoing API physical properties and those in the final product caused by drug product processing is considered. The focus of this review is on oral solid dosage forms and dry powder inhaler products for lung delivery.

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Process‐Induced Phase Transformation of Berberine Chloride Hydrates

Cited by 42 publications

References 16 publications

X-ray and Neutron Diffraction in the Study of Organic Crystalline Hydrates

X-ray and Neutron Diffraction in the Study of Organic Crystalline Hydrates

Weak C—H...X(X= O, N) hydrogen bonds in the crystal structure of dihydroberberine

Integration of active pharmaceutical ingredient solid form selection and particle engineering into drug product design

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