Frakefamide

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Frakefamide
Frakefamide.svg
Systematic (IUPAC) name
4-fluoro-L-phenylalanyl-N-[(2R)-2-(L-tyrosylamino)propanoyl]-L-phenylalaninamide
Clinical data
Legal status
?
Identifiers
CAS number 188196-22-7
ATC code None
PubChem CID 5493563
ChemSpider 4591495
Chemical data
Formula C30H34FN5O5 
Mol. mass 563.620 g/mol

Frakefamide (INN) is a synthetic, fluorinated opioid tetrapeptide with the amino acid sequence Tyr-D-Ala-(p-F)Phe-Phe-NH2 which acts as a peripherally-specific, selective μ-opioid receptor agonist.[1][2] Despite its inability to penetrate the blood-brain-barrier and enter the central nervous system,[1] frakefamide has potent analgesic effects and, unlike centrally-acting opioids like morphine, does not produce respiratory depression, indicating that its antinociceptive effects are mediated by peripheral μ-opioid receptors.[1][3] It was under development for the treatment of pain by AstraZeneca and Shire but was shelved after phase II clinical trials.[4][5]

See also[edit]

References[edit]

  1. ^ a b c Modalen AO, Quiding H, Frey J, Westman L, Lindahl S (March 2005). "A novel molecule (frakefamide) with peripheral opioid properties: the effects on resting ventilation compared with morphine and placebo". Anesthesia and Analgesia 100 (3): 713–7, table of contents. doi:10.1213/01.ANE.0000145011.75545.C5. PMID 15728057. 
  2. ^ Jeffrey K. Aronson (30 November 2009). Meyler's Side Effects of Analgesics and Anti-Inflammatory Drugs. Elsevier. p. 84. ISBN 978-0-444-53273-2. Retrieved 27 April 2012. 
  3. ^ Modalen AO, Quiding H, Frey J, Westman L, Lindahl S (January 2006). "A novel molecule with peripheral opioid properties: the effects on hypercarbic and hypoxic ventilation at steady-state compared with morphine and placebo". Anesthesia and Analgesia 102 (1): 104–9. doi:10.1213/01.ANE.0000184254.85567.80. PMID 16368813. 
  4. ^ Neal G. Anderson (15 April 2012). Practical Process Research and Development: A Guide for Organic Chemists. Academic Press. p. 4. ISBN 978-0-12-386537-3. Retrieved 27 April 2012. 
  5. ^ Chas Bountra; Rajesh Munglani; William K. Schmidt (13 May 2003). Pain: Current Understanding, Emerging Therapies, And Novel Approaches To Drug Discovery. CRC Press. p. 400. ISBN 978-0-8247-8865-0. Retrieved 27 April 2012.