| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H21NO2.ClH |
| Molecular Weight | 283.794 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCCN1CCO[C@H]2[C@H]1CCC3=CC=C(O)C=C23
InChI
InChIKey=NNEACMQMRLNNIL-CTHHTMFSSA-N
InChI=1S/C15H21NO2.ClH/c1-2-7-16-8-9-18-15-13-10-12(17)5-3-11(13)4-6-14(15)16;/h3,5,10,14-15,17H,2,4,6-9H2,1H3;1H/t14-,15-;/m1./s1
| Molecular Formula | C15H21NO2 |
| Molecular Weight | 247.3327 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Naxagolide (MK-458; L 647,339; (+)-PHNO) is a dopamine D2/D3-receptor agonist, which was studied for the treatment of patients with Parkinson's disease, but further study was discontinued. In addition, was discovered, that Naxagolide C-11 ([(11)C]-(+)-PHNO) was a potential radiotracer for imaging the high-affinity state of dopamine D2 receptors with positron emission tomography (PET) in human subjects. This radiotracer is a suitable for imaging the agonist binding sites (denoted D(2HIGH) and D(3)) of these receptors. PET studies in nonhuman primates documented that, in vivo, [(11)C]-(+)-PHNO displays a relative selectivity for D(3) compared with D(2HIGH) receptor sites and that the [(11)C]-(+)-PHNO signal is enriched in D(3) contribution compared with conventional ligands such as [(11)C] raclopride. Recently was published article reflects the relationship between social attachment and dopamine D2/3 receptor availability in the brains of healthy humans using [11C]-(+)-PHNO.
CNS Activity
Originator
Approval Year
Sourcing
PubMed
Sample Use Guides
In vitro binding characteristics of the dopamine D₃/D₂ antagonist [³H]raclopride were compared to the D₃/D₂ agonist [³H](+)-PHNO (Naxagolide) in membrane preparations from rat striatum, cerebellum Lobules 9 and 10 (CB L9,10), and other cerebellar regions. In striatum, both radioligands labeled a single binding site. [³H](+)-PHNO showed higher affinity, though lower B(max) , compared with [³H]raclopride and was sensitive to inhibition by Gpp(NH)p. [³H](+)-PHNO showed significant specific binding to CB L9,10 membranes with higher affinity compared to striatal membranes. [³H](+)-PHNO binds to a high- and a low-affinity binding site in CB L9,10 membranes; the high-affinity site was not Gpp(NH)p-sensitive. [³H](+)-PHNO did not significantly bind cerebellum left hemisphere membranes.
