AT-076

AT-076
Identifiers
	IUPAC name (3R)-7-hydroxy-N-[(2S)-1-[4-(3-hydroxyphenyl)piperidin-1-yl]-3-methylbutan-2-yl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide;
CAS Number	1657028-64-2;
PubChem CID	91938095;
ChemSpider	58145111;
UNII	NT43S9BKJ2;
Chemical and physical data
Formula	C26H35N3O3
Molar mass	437.584 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)[C@@H](CN1CCC(CC1)C2=CC(=CC=C2)O)NC(=O)[C@H]3CC4=C(CN3)C=C(C=C4)O;
	InChI InChI=1S/C26H35N3O3/c1-17(2)25(16-29-10-8-18(9-11-29)19-4-3-5-22(30)12-19)28-26(32)24-14-20-6-7-23(31)13-21(20)15-27-24/h3-7,12-13,17-18,24-25,27,30-31H,8-11,14-16H2,1-2H3,(H,28,32)/t24-,25-/m1/s1; Key:LGYDWJJZDCXEOV-JWQCQUIFSA-N;

AT-076 is a so-called opioid "pan" antagonist and is the first reasonably balanced antagonist known of all four opioid receptor types.^[1] It acts as a silent antagonist of all four of the opioid receptors, behaving as a competitive antagonist of the μ-opioid receptor (K_i = 1.67 nM) and δ-opioid receptor (K_i = 19.6 nM) and as a noncompetitive antagonist of the κ-opioid receptor (K_i = 1.14 nM) and nociceptin receptor (K_i = 1.75 nM).^[1] AT-076 was derived from the selective κ-opioid receptor antagonist JDTic via removal of the 3,4-dimethyl group of the trans-(3R,4R)-dimethyl-4-(3-hydroxyphenyl)piperidine antagonist scaffold which increased affinity for the nociceptin receptor by 10-fold and for the μ- and δ-opioid receptors by 3-6-fold.^[1]

References

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