Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Regular Articles
Crystal and Molecular Structure of an (S)-(+)-Enantiomer of Modafinil, a Novel Wake-Promoting Agent
Yasuko InKoji TomooToshimasa IshidaYasuhiko Sakamoto
Author information
JOURNAL FREE ACCESS

2004 Volume 52 Issue 10 Pages 1186-1189

Details
Abstract
The (+)-enantiomer of modafinil [(RS)-2-(diphenylmethylsulfinyl)acetamide], a novel wake-promoting agent, was clarified to be S-configuration by X-ray crystal structure analysis. The crystal consists of two crystallographically independent conformers that are different at the torsion angles around the sulfinylacetamide moiety, and this results from the molecular packing requirement to form a two-dimensional hydrogen-bonding network via neighboring amide groups in the crystal. The crystal structure is characterized by the formation of alternative hydrophobic and hydrophilic layers, which are formed among the symmetry-translated assemblies of diphenylmethyl and sulfinylacetamide moieties, respectively. The spatial orientation between the diphenyl and amide groups is believed to be important for the activity of modafinil.
Content from these authors
© 2004 The Pharmaceutical Society of Japan
Previous article Next article
feedback
Top