Frakefamide

Frakefamide

Frakefamide
Systematic (IUPAC) name
4-fluoro-L-phenylalanyl-N-[(2R)-2-(L-tyrosylamino)propanoyl]-L-phenylalaninamide
Clinical data
Legal status
?
Identifiers
CAS number
ATC code None
PubChem
ChemSpider
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

References

  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.  
  2. ^ Jeffrey K. Aronson (30 November 2009). Meyler's Side Effects of Analgesics and Anti-Inflammatory Drugs. Elsevier. p. 84.  
  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.  
  4. ^ Neal G. Anderson (15 April 2012). Practical Process Research and Development: A Guide for Organic Chemists. Academic Press. p. 4.  
  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.