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Issue 7, 2009
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The crystal structure of the API Montelukast

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Abstract

The sodium salt of the title compound (1-{[(R)-m-(E)-2-(7-chloroquinol-2-yl)vinyl)]-a-[2-(1-hydroxy-1-methylethyl)phenylethyl]-benzylthio}-methyl)cyclopropane acetic acid (1), known as Montelukast (a free acid), is a potent and selective leukotriene D-4 receptor antagonist. With an annual turnover of over 3 billion US dollars, it still attracts considerable interest in current pharmaceutical research, however, up until now no structural information has been available. The unit cell contains two symmetry independent molecules, which are connected to long ribbons along the c-axis viahydrogen bonds. Lattice energy minimizations reveal that the main part of the lattice energy may be attributed to multipole–multipole interactions between highly polarized Montelukast moieties. However, it seems that the comparable small contributions of the above mentioned hydrogen bonds are essential structure directing ingredients for crystallization.

Graphical abstract: The crystal structure of the API Montelukast

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Article information


Submitted
18 Dec 2008
Accepted
09 Feb 2009
First published
10 Mar 2009

CrystEngComm, 2009,11, 1306-1308
Article type
Paper

The crystal structure of the API Montelukast

J. Thun, W. Milius, B. Wedel, A. Ridder, P. Moersdorf and J. Breu, CrystEngComm, 2009, 11, 1306
DOI: 10.1039/B822821C

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