BU09059 - Misplaced Pages

Chemical compound Pharmaceutical compound

BU09059
Identifiers

IUPAC name ethyl 2-{formamido}-3-propanoate
CAS Number	1541206-05-6
PubChem CID	134817175
Chemical and physical data
Formula	C₂₈H₃₇N₃O₅
Molar mass	495.620 g·mol
3D model (JSmol)	Interactive image
SMILES CCOC(=O)C(CN1CC(C)((C)C1)c2cccc(O)c2)NC(=O)3Cc4ccc(O)cc4CN3
InChI InChI=1S/C28H37N3O5/c1-4-36-27(35)25(30-26(34)24-13-19-8-9-23(33)12-20(19)15-29-24)17-31-11-10-28(3,18(2)16-31)21-6-5-7-22(32)14-21/h5-9,12,14,18,24-25,29,32-33H,4,10-11,13,15-17H2,1-3H3,(H,30,34)/t18-,24+,25?,28+/m0/s1 Key:RKGRJMYCISUSNK-XTNINKNLSA-N

BU09059 is a potent, selective, short-acting (non-"inactivating") antagonist of the κ-opioid receptor (KOR). It was derived from the irreversible (long-acting) KOR antagonist JDTic in search of an antagonist with a reversible profile of inactivation of the KOR that could be used with less concern to treat psychiatric disorders. In addition to its reversibility, BU09059 is much more selective for the KOR than JDTic, showing 15-fold and 616-fold preference for the KOR over the μ- and δ-opioid receptors (K_i = 1.72 nM, 26.5 nM, and 1060 nM, respectively).

References

^ Casal-Dominguez JJ, Furkert D, Ostovar M, Teintang L, Clark MJ, Traynor JR, et al. (March 2014). "Characterization of BU09059: a novel potent selective κ-receptor antagonist". ACS Chemical Neuroscience. 5 (3): 177–84. doi:10.1021/cn4001507. PMC 3963132. PMID 24410326.
^ Urbano M, Guerrero M, Rosen H, Roberts E (May 2014). "Antagonists of the kappa opioid receptor". Bioorganic & Medicinal Chemistry Letters. 24 (9): 2021–32. doi:10.1016/j.bmcl.2014.03.040. PMID 24690494.