Safer, More Versatile Acetaminophen | August 3, 2009 Issue - Vol. 87 Issue 31 | Chemical & Engineering News
Volume 87 Issue 31 | p. 28 | Concentrates
Issue Date: August 3, 2009

Safer, More Versatile Acetaminophen

Synthesis of more soluble and less toxic version of a common painkiller scales up
Department: Science & Technology
Keywords: acetaminophen, neuropathic pain, pain reliever, scale up
SCP-123 consists of a hydrolyzed saccharin substituent (red) clipped onto acetaminophen.
SCP-123 consists of a hydrolyzed saccharin substituent (red) clipped onto acetaminophen.

A simple, hydrolyzed saccharin derivative of acetaminophen being geared up for clinical studies is potentially safer and can treat a broader range of ailments than the parent compound, according to Kenneth W. Narducy of St Charles Pharmaceuticals, in New Orleans, which is developing the drug. In the latest aspect of the research, Narducy teamed up with Mark L. Trudell and coworkers of the University of New Orleans to devise a multigram synthesis of the compound, dubbed SCP-123, in 47% overall yield and better than 99% purity by crystallization (Org. Process Res. Dev. 2009, 13, 820). Acetaminophen is one of the world's most widely used pain relievers, but it is hampered by low water solubility and can cause liver damage at high doses. SCP-123 is just as potent as acetaminophen at relieving pain but has better water solubility and significantly diminished liver toxicity. And unlike acetaminophen, SCP-123 shows promise for treating neuropathic pain, which stems from nervous system damage rather than stimulation of pain receptors. Last year, St Charles Pharmaceuticals was awarded a special $3 million grant from the National Institute of Neurological Disorders & Stroke to help advance SCP-123 to clinical trials.

Chemical & Engineering News
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