Conversion of Pregabalin to 4-Isobutylpyrrolidone-2

Amanda M Drachnik; Harshita Kumari; Collin M Mayhan; Drew A Fowler; Wei G Wycoff; Charles L Barnes; John E Adams; Carol A Deakyne; Jerry L Atwood

doi:10.1016/j.xphs.2017.03.044

Conversion of Pregabalin to 4-Isobutylpyrrolidone-2

J Pharm Sci. 2017 Oct;106(10):3095-3102. doi: 10.1016/j.xphs.2017.03.044. Epub 2017 Apr 15.

Authors

Amanda M Drachnik¹, Harshita Kumari², Collin M Mayhan¹, Drew A Fowler¹, Wei G Wycoff¹, Charles L Barnes¹, John E Adams¹, Carol A Deakyne¹, Jerry L Atwood¹

Affiliations

¹ Department of Chemistry, University of Missouri-Columbia, 601 S. College Avenue, Columbia, Missouri 65211.
² James L. Winkle College of Pharmacy, University of Cincinnati, 231 Albert Sabin Way, Medical Science Building #3109C, Ohio 45267-0514. Electronic address: [email protected].

PMID: 28419825
DOI: 10.1016/j.xphs.2017.03.044

Abstract

Solid-state studies of C-butyl-resorcin[4]arene with pregabalin (Lyrica, Nervalin) in nitrobenzene yielded a cocrystal of C-butyl-resorcin[4]arene with 4-isobutylpyrrolidone-2. A combined experimental and quantum chemical investigation was implemented to further our understanding of the factors affecting the conversion process.

Keywords: DFT; DMSO; cocrystal; resorcin[4]arene; self-assembly.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Nitrobenzenes / chemistry
Pregabalin / chemistry*
Pyrrolidinones / chemistry*

Substances

Nitrobenzenes
Pyrrolidinones
Pregabalin
nitrobenzene