structural examination of 6-methylsulphonylphenanthro- [9,10-c]-furan-1(3h)-one—a rofecoxib degradation product结构检查6-methylsulphonylphenanthro -[9,10 c]-furan-1(3 h)一个万络降解产物.pdfVIP

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structural examination of 6-methylsulphonylphenanthro- [9,10-c]-furan-1(3h)-one—a rofecoxib degradation product结构检查6-methylsulphonylphenanthro -[9,10 c]-furan-1(3 h)一个万络降解产物.pdf

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structural examination of 6-methylsulphonylphenanthro- [9,10-c]-furan-1(3h)-one—a rofecoxib degradation product结构检查6-methylsulphonylphenanthro -[9,10 c]-furan-1(3 h)一个万络降解产物

Pharmaceuticals 2010, 3, 369-378; doi:10.3390/ph3020369 OPEN ACCESS pharmaceuticals ISSN 1424-8247 /journal/pharmaceuticals Article Structural Examination of 6-Methylsulphonylphenanthro- [9,10-C]-furan-1(3H)-one—A Rofecoxib Degradation Product Pamela M. Dean Department of Chemistry, Monash University, Wellington Road, Clayton, Victoria, 3800, Australia; E-Mail: pamela.dean@.au; Tel.: +61-3-990-54599; Fax: +61-3-990-54597 Received: 14 December 2009; in revised form: 12 January 2010 / Accepted: 21 January 2010 / Published: 1 February 2010 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 1. Introduction The therapeutic properties of willow bark were known since antiquity, with the Egyptians and Assyrians using a decoction of myrtle and willow leaves to produce analgesia. Even Hippocrates, regarded as the father of medicine, recommended the chewing of willow leaves for this purpose. The active compound wi