Frakefamide

Frakefamide
Systematic (IUPAC) name
	4-fluoro-L-phenylalanyl-N-[(2R)-2-(L-tyrosylamino)propanoyl]-L-phenylalaninamide
Identifiers
CAS Number	188196-22-7
ATC code	None
PubChem	CID: 5493563
ChemSpider	4591495
Chemical data
Formula	C30H34FN5O5
Molecular mass	563.620 g/mol
	SMILES Fc1ccc(cc1)C[C@H](N)C(=O)N[C@H](C(=O)NC(=O)[C@H](NC(=O)[C@@H](N)Cc2ccc(O)cc2)C)Cc3ccccc3 ;
	InChI InChI=1S/C30H34FN5O5/c1-18(34-28(39)24(32)16-21-9-13-23(37)14-10-21)27(38)36-30(41)26(17-19-5-3-2-4-6-19)35-29(40)25(33)15-20-7-11-22(31)12-8-20/h2-14,18,24-26,37H,15-17,32-33H2,1H3,(H,34,39)(H,35,40)(H,36,38,41)/t18-,24+,25+,26+/m1/s1 ; Key:HESSKXOHGGYIFY-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]

References

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