Polymorphism of Thiamine Hydrochloride

Watanabe, Atsushi; Nakamachi, Hideo

doi:10.1248/yakushi1947.96.10_1236

Cited by 10 publications

(15 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thiamine hydrochloride (Vitamin B 1 /THCl), the model compound, exists in two distinct hydrate forms: (a) a nonstoichiometric hydrate (NSH) containing up to ∼1 mol of water per mole of THCl (5.1%, w/w), which dehydrates readily to form an isomorphic desolvate (ID) with minimal change in lattice packing and (b) a hemihydrate (HH) which is extremely resistant to dehydration 19–21…”

Section: Introductionmentioning

confidence: 99%

Insights into the dehydration behavior of thiamine hydrochloride (Vitamin B1) hydrates: Part I

Chakravarty

Berendt

Munson

et al. 2010

Journal of Pharmaceutical Sciences

View full text Add to dashboard Cite

Section: Introductionmentioning

confidence: 99%

Insights into the dehydration behavior of thiamine hydrochloride (Vitamin B1) hydrates: Part I

Chakravarty

Berendt

Munson

et al. 2010

Journal of Pharmaceutical Sciences

View full text Add to dashboard Cite

“…Pseudo-Crystalline Transformation Behavior from Form I to Form II At the beginning of this experiment, the crystal forms of those materials were checked by XRPD for according to the XRPD patterns of form I and form II on the previous reports, [2][3][4] and solid state NMR for the purity of crystal forms. In this result, those materials were confirmed form I and form II, and had good crystal purity.…”

Section: Resultsmentioning

confidence: 99%

“…4 XRPD XRPD data were obtained using a Rigaku (Tokyo, Japan) RINT2200 powder diffraction system, equipped with an Ultima ϩ (Tokyo, Japan) goniometer I-type in q/2q geometry. The X-ray generator was operated at 40 kV and 20 mA, using CuKa radiation (wavelength 1.5418 Å).…”

Section: Methodsmentioning

confidence: 99%

“…These crystal structures were elucidated using single-crystal X-ray structural analysis, form I by Kraut and Reed in 1962, 1) form II by Watanabe et al in 1979, 2) and form III by Te et al in 2003. 3) Since then, there have been various reports on the physiochemical properties of these pseudo-polycrystalline forms. 4,5) The relationship between form I (monohydrate) and form III (anhydrate) is that of the enantiotropic transformation accompanying changes in the hydration state. The pseudo-crystalline transformation from form I to form III is achieved by drying, and form III returns to form I by rehydration.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Study of the Pseudo-Crystalline Transformation from Form I to Form II of Thiamine Hydrochloride (Vitamin B1)

Masuda¹,

Ishige²,

Yamada³

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

There are three types of pseudo-polycrystalline forms of thiamine hydrochloride (vitamin B 1 ): form I (monohydrate); form II (hemihydrate); and form III (anhydrate). These crystal structures were elucidated using single-crystal X-ray structural analysis, form I by Kraut and Reed in 1962, 1) form II by Watanabe et al. in 1979, 2) and form III by Te et al. in 2003. 3) Since then, there have been various reports on the physiochemical properties of these pseudo-polycrystalline forms. 4,5) The relationship between form I (monohydrate) and form III (anhydrate) is that of the enantiotropic transformation accompanying changes in the hydration state. The pseudo-crystalline transformation from form I to form III is achieved by drying, and form III returns to form I by rehydration. The reversibility of form I and form III as well as the dehydration behavior of form II were reported in detail based on each crystal structure. 6,7) It was reported that the pseudo-crystalline transformation from form I to form II occurs when form I is stored for a long time under usual laboratory conditions, in a wet granulation process, in a slurry wash with water, or under specific conditions of 40°C and 75% relative humidity (RH). 2,8) However, the elucidation of the rate of the pseudo-crystalline transformation depending on storage conditions was lacking. The present study was therefore undertaken to examine the pseudo-crystalline transformation behavior from form I to form II in detail, including kinetic analysis by varying the storage conditions of temperature and humidity. In addition, we aimed to determine whether the rate was affected by formulation with establishing the most appropriate method to detect small amounts of the crystalline polymorph in tablets.As part of the evaluation of the quality of tablets, which are the final product, the evaluation of crystalline forms of drug substances is important in the quality control of pharmaceutical products. Even if the crystalline form of drug substances in a tablet changes, it is not easy to confirm small amounts of crystalline change in drug substances when combined with various excipients. In this study, we observed changes in the crystalline forms of thiamine hydrochloride in tablets using the synchrotron X-ray powder diffraction (XRPD) method which allows sensitive measurement with parallel bright X-ray beams. We have optimized the methodology of synchrotron XRPD to detect small amount of the drug substance. The detection rate using this methodology is equivalent to about 0.02% of the amount of drug substances in a common size tablet. The details of this methodology will be published separately in the near future. In addition to the high sensitivity, it should be emphasized that the XRPD method is a non-destructive inspection, and the whole tablets can be used as specimen without grinding preparation by utilizing the advantage of highly brilliant and parallel synchrotron radiation. ExperimentalMaterials Form I thiamine hydrochloride crystals were purchased from Sigma Chemical (...

show abstract

“…The preparation and the preliminary characterization of the methanol solvate have been reported. 9 However, no attempt was made to relate the structure of THCl phases to their stability. Earlier, while evaluating the dehydration behavior of NSH, we hypothesized that, despite the lack of continuous hydration channels in the crystal lattice, cooperative deformation of the thiamine molecules allowed a nondisruptive departure of water molecules during dehydration.…”

Section: Introductionmentioning

confidence: 99%

Characterization and Structure Analysis of Thiamine Hydrochloride Methanol Solvate

Chakravarty

Suryanarayanan

2010

Crystal Growth & Design

View full text Add to dashboard Cite

Thiamine hydrochloride (THCl) forms a monomethanolate (MM) upon exposure of crystalline thiamine phases (thiamine hydrochloride hemihydrate/HH, nonstoichiometric hydrate/NSH, and anhydrate/AH) to anhydrous methanol (solvent and vapor). Desolvation of MM at 50-80°C resulted in the formation of a poorly crystalline intermediate which crystallized to AH at elevated temperatures (g150°C). When exposed to water vapor (11-75% RH, RT), MM transformed to HH (NSH was detected at e40% RH), while exposure to polar solvent vapor resulted in direct formation of AH. MM was stable in the presence of nonpolar (benzene and hexane) solvent vapor. Crystal structure analysis revealed a near identical H-bonding network in the two solvate (MM, and NSH with 1 mol water/mol THCl) lattices. The structure of MM as well as the solvent properties were identified as the key factors influencing both the kinetics of desolvation of MM and the nature of the product phase.

show abstract

Polymorphism of Thiamine Hydrochloride

Cited by 10 publications

References 0 publications

Insights into the dehydration behavior of thiamine hydrochloride (Vitamin B1) hydrates: Part I

Insights into the dehydration behavior of thiamine hydrochloride (Vitamin B1) hydrates: Part I

Study of the Pseudo-Crystalline Transformation from Form I to Form II of Thiamine Hydrochloride (Vitamin B1)

Characterization and Structure Analysis of Thiamine Hydrochloride Methanol Solvate

Contact Info

Product

Resources

About