(<i>R</i>)-Baclofen [(<i>R</i>)-4-amino-3-(4-chlorophenyl)butanoic acid]

Belov, Feodor; Villinger, Alexander; Langermann, Jan von

doi:10.1107/s2056989021012809

Cited by 1 publication

(1 citation statement)

References 18 publications

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“…APIs Phenibut ((RS)-4-amino-3-phenylbutanoic acid) and Baclofen ((RS)-4-amino-3-(4-chloro-phenyl) butanoic acid) are structurally similar γ-amino butanoic acid (GABA) derivatives with a phenyl subunit on C3. Both pose a chiral center in that position, with the (R)-form being the eutomer [25][26][27][28]. The sole difference is a chloro-subunit on the phenyl-ring in Baclofen in the p-position in regard to the GABA chain.…”

Section: Introductionmentioning

confidence: 99%

A Lection in Humbleness: Crystallization of Chiral and Zwitterionic APIs Baclofen and Phenibut

et al. 2022

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Crystallization and multicomponent crystal formation of active pharmaceutical ingredients Baclofen and Phenibut with dicarboxylic acid co-formers are discussed. The crystallization process of several crystalline entities is elucidated via single crystal—as well as powder X-ray—diffraction, followed by thermal analysis and phase stability studies over time. Both APIs form increasingly complex crystalline phases with co-formers malic and tartaric acid, where phase purity of a desired compound is not necessarily a given. Therefore, the influence of different solution and milling environments during crystallization on the outcome is studied. Emphasis is laid on how molecular influences such as the chirality, propensity to form hydrates as well as low solubility of Baclofen and Phenibut impede attempts to gather high-quality single crystals. The results highlight that targeted crystallization of these compounds with dicarboxylic acids can be difficult and unreliable.

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Section: Introductionmentioning

confidence: 99%