Frakefamide

Frakefamide

Clinical data
ATC code	None
Identifiers
IUPAC name (2S)-2-[(2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]-N-[(1S)-1-carbamoyl-2-phenylethyl]-3-(4-fluorophenyl)propanamide
Synonyms	L-Tyrosyl-D-alanyl-4-fluoro-L-phenylalanyl-L-phenylalaninamide
CAS Number	188196-22-7
PubChem (CID)	9829352
ChemSpider	8005088
UNII	DM32B4GU70
Chemical and physical data
Formula	C30H34FN5O5
Molar mass	563.62 g/mol
3D model (Jmol)	Interactive image
SMILES C[C@H](C(=O)N[C@@H](CC1=CC=C(C=C1)F)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N)NC(=O)[C@H](CC3=CC=C(C=C3)O)N
InChI InChI=1S/C30H34FN5O5/c1-18(34-29(40)24(32)15-20-9-13-23(37)14-10-20)28(39)36-26(17-21-7-11-22(31)12-8-21)30(41)35-25(27(33)38)16-19-5-3-2-4-6-19/h2-14,18,24-26,37H,15-17,32H2,1H3,(H2,33,38)(H,34,40)(H,35,41)(H,36,39)/t18-,24+,25+,26+/m1/s1 Key:GTPHQORJKFJIRB-JTQLPTLWSA-N

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

• Casokefamide
• Metkefamide

References

1. 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.