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Pharmaceuticals 2010, 3(2), 369-378; doi:10.3390/ph3020369
Article

Structural Examination of 6-Methylsulphonylphenanthro- [9,10-C]-furan-1(3H)-one—A Rofecoxib Degradation Product

Department of Chemistry, Monash University, Wellington Road, Clayton, Victoria, 3800, Australia
Received: 14 December 2009 / Revised: 12 January 2010 / Accepted: 21 January 2010 / Published: 1 February 2010
(This article belongs to the collection Non-Steroidal Anti-Inflammatory Drugs)
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Abstract

In the attempt to discover a new polymorph of rofecoxib (Vioxx®), an unexpected product resulted. The product was characterised by chemical composition, thermal behaviour and structure and found to be 6-methylsulphonylphenanthro-[9,10-C] furan-1(3H)-one, a photo-cyclization degradation product of rofecoxib. This is a significant finding because it indicates that without appropriate control of the recrystallisation procedures, the structural integrity of rofecoxib may be seriously compromised.
Keywords: rofecoxib; structural characterisation; NSAID; crystallography rofecoxib; structural characterisation; NSAID; crystallography
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Dean, P.M. Structural Examination of 6-Methylsulphonylphenanthro- [9,10-C]-furan-1(3H)-one—A Rofecoxib Degradation Product. Pharmaceuticals 2010, 3, 369-378.

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