Structural Characterization of Cevimeline and Its Trans-Impurity by Single Crystal XRD

Dmitrijs Stepanovs, Zenta Tetere, Irisa Rāviņa, Viktors Kumpiņš, Daina Zicāne, Ērika Bizdēna, Jānis Bogans, Irina Novosjolova, Agnese Grigaloviča, Remo Merijs Meri, Juris Fotins, Maksims Čerkasovs, Anatoly Mishnev, etc.

J Pharm Biomed Anal. 2016 Jan 25;118:404-409.

PMID: 26609680

Abstract:

Cevimeline is muscarinic receptor agonist which increases secretion of exocrine glands. Cevimeline base is a liquid (m.p. 20-25 °C) at ambient conditions, therefore its pharmaceutical formulation as a solid hydrochloride hemihydrate has been developed. The synthesis of cevimeline yields its cis- and trans-isomers and only the cis-isomer is recognized as the API and used in the finished formulation. In this study structural and physicochemical investigations of hydrochloride hemihydrates of cis- and trans-cevimelines have been performed. Single crystal X-ray analyses of both cis- and trans-isomers of cevimeline are reported here for the first time. It was found that the cis-isomer, the API, has less dense crystal packing, lower melting point and higher solubility in comparison to the trans-isomer.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP153504702	Cevimeline hydrochloride hemihydrate		153504-70-2	Price