FE 200665
| FE 200665 | ||
|---|---|---|
 | ||
| IUPAC name (R)-2-((R)-2-((R)-2-amino-3-phenylpropanamido)-3-phenylpropanamido)-N-((R)-5-guanidino-1-oxo-1-((pyridin-4-ylmethyl)amino)pentan-2-yl)hexanamide | ||
| Other names CR 665; JNJ 38488502 | ||
| Identifiers | ||
| CAS number | 228546-92-7  | |
| Jmol-3D images | {{#if:O=C(NCC1=CC=NC=C1)[C@H](NC([C@H](NC([C@@H](CC2=CC=CC=C2)NC([C@@H](CC3=CC=CC=C3)N)=O)=O)CCCC)=O)CCCNC(N)=N|Image 1 | |
| ||
| Properties | ||
| Molecular formula | C36H49N9O4 | |
| Molar mass | 671.83 g mol−1 | |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| Infobox references | ||
FE 200665 (H-D-Phe-D-Phe-D-Nle-D-Arg-NH-4-Picolyl), also known as CR665, is an all D-amino acid peptide that acts as a peripherally restricted κ-opioid receptor agonist. The selectivity for FE 200665 is 1/16,900/84,600 for the human κ, μ, and δ opioid receptors, respectively. The dose of FE 200665 required to produce motor impairment (measure of CNS penetration) was 548 times higher than the dose required for antinociceptive activity.[1] It is being developed for use by Cara Therapeutics under the code CR665.
A small, double blind study was done in healthy humans to determine the analgesic effects. CR665 was dosed at 0.36 mg/kg I.V., and was compared to 15 mg oxycodone orally. CR665 had analgesic effects on visceral pain, but produced a hyperalgesic response in a skin pinch test.[2]
References
- ↑ Vanderah, T. W.; Largent-Milnes, T.; Lai, J.; Porreca, F.; Houghten, R. A.; Menzaghi, F.; Wisniewski, K.; Stalewski, J.; Sueiras-Diaz, J.; Galyean, R.; Schteingart, C.; Junien, J. L.; Trojnar, J.; Rivière, P. J. (2008). "Novel D-Amino Acid Tetrapeptides Produce Potent Antinociception by Selectively Acting at Peripheral κ-Opioid Receptors". European Journal of Pharmacology 583 (1): 62–72. doi:10.1016/j.ejphar.2008.01.011. PMID 18282565.
- ↑ Arendt-Nielsen, L.; Olesen, A. E.; Staahl, C.; Menzaghi, F.; Kell, S.; Wong, G. Y.; Drewes, A. M. (2009). "Analgesic Efficacy of Peripheral κ-Opioid Receptor Agonist CR665 Compared to Oxycodone in a Multi-modal, Multi-Tissue Experimental Human Pain Model: Selective Effect on Visceral Pain". Anesthesiology 111 (3): 616–624. doi:10.1097/ALN.0b013e3181af6356. PMID 19672186.