Encyclopedia of Inflammatory Diseases

Living Edition
| Editors: Michael J. Parnham

Propionic Acid Derivative Drugs (Profens)

  • Richard O. Day
  • Garry G. Graham
  • Kenneth Williams
Living reference work entry

Later version available View entry history

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DOI: https://doi.org/10.1007/978-3-0348-0620-6_58-3
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Synonyms

Phenylpropanoic acids; Phenylpropionic acids; Phenylpropanoates; Phenylpropionates; 2-methylphenylacetates; 2-methylphenylacetic acids. There are a large number of profens available commercially including: Carprofen; Naproxen; Fenoprofen; Flurbiprofen; Ibuprofen; Ketoprofen; Tiaprofenic acid

Definition

The profens are a category of nonselective, nonsteroidal anti-inflammatory drugs (NSAIDs). They reduce pain (analgesia), body temperature in fever (antipyresis), signs of inflammation (anti-inflammatory activity), and, in mice, slow the development of cancers.

Chemical Structures and Properties

The profens are derivatives of 2-phenylpropanoic acid. All contain a chiral center resulting in the formation of two enantiomers (R and S) of each profen (Fig. 1). The profens are available mostly as their racemates, i.e., equal mixtures of the R and S stereoisomers. The major exception is naproxen which is available as its pure S-enantiomer, but ibuprofen and ketoprofen are also...

Keywords

Analgesic Activity Prostaglandin Synthesis Tiaprofenic Acid Immunological Action Nonselective NSAID 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
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References

  1. Bishay, P., Schmidt, H., Marian, C., Haussler, A., Wijnvoord, N., Ziebell, S., et al. (2010). R-flurbiprofen reduces neuropathic pain in rodents by restoring endogenous cannabinoids. PLoS ONE, 5(5), e10628.PubMedCentralCrossRefPubMedGoogle Scholar
  2. Catella-Lawson, F., Reilly, M. P., Kapoor, S. C., Cucchiara, A. J., DeMarco, S., Tournier, B., et al. (2001). Cyclooxygenase inhibitors and the antiplatelet effects of aspirin. New England Journal of Medicine, 345(25), 1809–1817.CrossRefPubMedGoogle Scholar
  3. CNT, & Coxib and traditional NSAID Trialists’ (CNT) Collaboration. (2013). Vascular and upper gastrointestinal effects of non-steroidal anti-inflammatory drugs: Meta-analyses of individual participant data from randomised trials. Lancet. doi:10.1016/S0140-6736(1013)60900-60909.Google Scholar
  4. Duggan, K. C., Hermanson, D. J., Musee, J., Prusakiewicz, J. J., Scheib, J. L., Carter, B. D., et al. (2011). (R)-Profens are substrate-selective inhibitors of endocannabinoid oxygenation by COX-2. Nature Chemical Biology, 7(11), 803–809.PubMedCentralCrossRefPubMedGoogle Scholar
  5. Graham, G. G., & Williams, K. M. (2004). Metabolism and pharmacokinetics of ibuprofen. In K. D. Rainsford (Ed.), Aspirin and related drugs (pp. 157–180). London: Taylor & Francis.Google Scholar
  6. Henry, D., Drew, A., & Beuzeville, S. (1999). Gastrointestinal adverse drug reactions attributed to ibuprofen. In K. D. Rainsford (Ed.), Ibuprofen (pp. 433–458). London: Taylor & Francis.Google Scholar
  7. Jerussi, T. P., Caubet, J. F., McCray, J. E., & Handley, D. A. (1998). Clinical endoscopic evaluation of the gastroduodenal tolerance to (R)- ketoprofen, (R)- flurbiprofen, racemic ketoprofen, and paracetamol: A randomized, single-blind, placebo-controlled trial. Journal of Clinical Pharmacology, 38(2 Suppl), 19S–24S.CrossRefPubMedGoogle Scholar
  8. Latimer, N., Lord, J., Grant, R., O’Mahony, R., Dickson, J., & Conaghan, P. (2009). Cost effectiveness of COX 2 selective inhibitors and traditional NSAIDs alone or in combination with a proton pump inhibitor for people with osteoarthritis. British Medical Journal, 339, b2538.PubMedCentralCrossRefPubMedGoogle Scholar
  9. Lötsch, J., Geisslinger, G., Mohammadian, P., Brune, K., & Kobal, G. (1995). Effects of flurbiprofen enantiomers on pain-related chemo-somatosensory evoked potentials in human subjects. British Journal of Clinical Pharmacology, 40(4), 339–346.PubMedCentralCrossRefPubMedGoogle Scholar
  10. McGettigan, P., & Henry, D. (2011). Cardiovascular risk with non-steroidal anti-inflammatory drugs: Systematic review of population-based controlled observational studies. PLoS Medicine, 8(9), e1001098.PubMedCentralCrossRefPubMedGoogle Scholar
  11. Rainsford, K. D. (1999). Pharmacology and toxicology of ibuprofen. In K. D. Rainsford (Ed.), Ibuprofen, Taylor & Francis, London (pp. 145–275).Google Scholar
  12. Tegeder, I., Pfeilschifter, J., & Geisslinger, G. (2001). Cyclooxygenase-independent actions of cyclooxygenase inhibitors. FASEB Journal, 15(12), 2057–2072.CrossRefPubMedGoogle Scholar
  13. Wechter, W. J., McCracken, J. D., Kantoci, D., Murray, E. D., Quiggle, D., Leipold, D., et al. (1998). Mechanism of enhancement of intestinal ulcerogenicity of S-aryl propionic acids by their R-enantiomers in the rat. Digestive Diseases & Sciences, 43(6), 1264–1274.CrossRefGoogle Scholar

Copyright information

© Springer Basel 2013

Authors and Affiliations

  • Richard O. Day
    • 1
    • 2
  • Garry G. Graham
    • 1
    • 2
  • Kenneth Williams
    • 1
  1. 1.Department of Pharmacology, School of Medical SciencesUniversity of New South WalesSydneyAustralia
  2. 2.Department of Clinical Pharmacology and ToxicologySt Vincent’s HospitalSydneyAustralia