Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H21NO2 |
| Molecular Weight | 247.3327 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CCC3=C(C=C(O)C=C3)[C@@]1([H])OCCN2CCC
InChI
InChIKey=JCSREICEMHWFAY-HUUCEWRRSA-N
InChI=1S/C15H21NO2/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/t14-,15-/m1/s1
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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) |
0.24 nM [Ki] | ||
Target ID: P35462 Gene ID: 1814.0 Gene Symbol: DRD3 Target Organism: Homo sapiens (Human) |
0.6 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Studies on the involvement of dopamine D-1 and D-2 receptors in the anticonvulsant effect of dopamine agonists in various rodent models of epilepsy. | 1986 Aug 22 |
|
| MK 458, a selective and potent D2 receptor agonist in advanced Parkinson's disease. | 1988 Jun |
|
| Differential effects of D1 and D2 agonists in MPTP-treated primates: functional implications for Parkinson's disease. | 1990 Jun |
|
| D-2 agonists protect rodents against pilocarpine-induced convulsions by stimulating D-2 receptors in the striatum, but not in the substantia nigra. | 1991 May |
|
| Effect of D1 and D2 agonists and antagonists on dyskinesia produced by L-dopa in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated monkeys. | 1991 Oct |
|
| Differential effect of selective D-1 and D-2 dopamine receptor agonists on levodopa-induced dyskinesia in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine- exposed monkeys. | 1993 Oct |
|
| Radiosynthesis and evaluation of [11C]-(+)-4-propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazin-9-ol as a potential radiotracer for in vivo imaging of the dopamine D2 high-affinity state with positron emission tomography. | 2005 Jun 16 |
|
| Imaging dopamine D3 receptors in the human brain with positron emission tomography, [11C]PHNO, and a selective D3 receptor antagonist. | 2010 Aug 15 |
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.
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C166533
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C042631
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6101
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
