Ketoprofen Synthesis

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Ketoprofen Synthesis

• Brian R. Raines
• Organic Chemistry II

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Ketoprofen Presentation Overview

• Physical Properties
• Chemical Structure and Synonyms
• Background
• Origination
• Uses
• Synthesis
• Summary

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Ketoprofen - Physical Properties

• Chemical Formula - C16H14O3
• White crystalline powder
• MW 254.28
• MP 94-97º C
• Insoluble in water

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Ketoprofen - Chemical Structure
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Ketoprofen - Synonyms

• 3-Benzoyl-a-methyl-benzeneacetic acid
• 2-(3-benzoyl-phenyl)propionic acid
• Common Names
• Orudis, Oruvail, Alrheumat, Toprec, and others

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Ketoprofen - Background

• First synthesized in 1968 by Rhone-Poulenc.
• Is a NSAID (non-steroid anti-inflammatory drug)
• Used to treat mild to moderate pain and reduce
  fever.
• Can be combined with opoids to treat moderate
  to severe pain.
• Suppresses inflammation in a manner similar
  to steroids

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Ketoprofen - Background

• It is a non-selective COX (cyclooxygenase)
  inhibitor. This blocking of COX-1 and COX-2
  enzymes results in decreased production of
  prostoglandins.
• Prostoglandins are fatty acid derivatives
  produced by the body.

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Ketoprofen - Background

• COX-1 enzymes produce prostoglandins which help
  protect the digestive tract from stomach acid and
  also play a role in blood clotting.
• All NSAIDs are COX-1 inhibitors
• They may cause damage to the stomach such as
  ulcers
• They reduce clotting efficiency by effecting
  platelet function.

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Ketoprofen - Background

• COX-2 enzymes produce prostoglandins that respond
  to injuries such as sprains, burns, breaks or
  bacterial infection.
• Coxibs tend to block only COX-2 inhibitors.
• Less likely to damage the stomach
• May increase risk of cardiovascular problems.
  (Celebrex)

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Ketoprofen - Background

• FDA Warning - Wishy, washy. Maybe it will, maybe
  it wont.
• Label revisions that highlight the potential for
  increased risk of cardiovascular events and
  potentially life threatening gastrointestinal
  bleeding.

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Ketoprofen - Synthesis 1
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Ketoprofen - Synthesis 2 (Voskanian Synthesis)
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Ketoprofen - Summary

• Anti-inflammatory and antipyrretic drug.
• Benzophenone with a side chain containing a
  methyl group and carboxylic acid.
• Functions to block COX-1 and COX-2 production of
  prostoglandins.
• Warning regarding potential health hazards.
• Further study required.

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The End
No safety glasses. He loses community points