Frakefamide
From Wikipedia, the free encyclopedia
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| Systematic (IUPAC) name | |
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(2S)-2-[(2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]-N-[(1S)-1-carbamoyl-2-phenylethyl]-3-(4-fluorophenyl)propanamide
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| Identifiers | |
| CAS Number | 188196-22-7 |
| ATC code | None |
| PubChem | CID 9829352 |
| ChemSpider | 8005088 |
| UNII | DM32B4GU70 |
| Synonyms | L-Tyrosyl-D-alanyl-4-fluoro-L-phenylalanyl-L-phenylalaninamide |
| Chemical data | |
| Formula | C30H34FN5O5 |
| Molar mass | 563.62 g/mol |
| 3D model (Jmol) | Interactive image |
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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]
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
