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14. Schering-Plough
Fortune 500 rank: 212
2007 loss: $1.47 billion

Drugs are a blockbuster business. So when Schering-Plough's patent on allergy medication Claritin expired in 2003, the company needed to do something dramatic. It got a new CEO and launched a restructuring plan, which culminated with last year's $16 billion acquisition of European drugmaker Organon BioSciences.

Schering took a $4 billion charge related to the deal, which tanked earnings. But 2008 may not be much better: Vytorin, a cholesterol drug combination from Schering-Plough and Merck, is under fire from lawmakers who say the companies misrepresented its effectiveness.

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Last updated April 24 2008: 11:01 AM ET