NAXAGOLIDE HYDROCHLORIDE

Details

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

Structure Search

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

HIDE SMILES / InChI

Molecular Formula	C15H21NO2
Molecular Weight	247.3327
Charge	0
Count

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

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1676932 | https://www.ncbi.nlm.nih.gov/pubmed/26873034

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
D(2) dopamine receptor 58 Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16088951	Agonist 2752		0.24 nM [Ki]
D(3) dopamine receptor 16 Target ID: P35462 Gene ID: 1814.0 Gene Symbol: DRD3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16088951	Agonist 2752		0.6 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1676932	Primary		Phase II 1147	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P0003PR	https://www.1pchem.com/search?query=1P0003PR
Alfa Chemistry	26606	http://www.alfa-chemistry.com/search.aspx?q=26606
Alfa Chemistry	ACM100935997	http://www.alfa-chemistry.com/search.aspx?q=ACM100935997
Angene	AGN-PC-0WH1P4	http://www.angenechemical.com/productshow/AGN-PC-0WH1P4.html
Axon MedChem	1070	https://www.axonmedchem.com/product/1070
Axon MedChem	1071	https://www.axonmedchem.com/product/1071
BioSynth	J-501357	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/J-501357
BOC Sciences	100935-99-7	http://www.bocsci.com/description.asp?cas=100935-99-7
BOC Sciences	88058-88-2	http://www.bocsci.com/description.asp?cas=88058-88-2
BOC Sciences	99705-65-4	http://www.bocsci.com/description.asp?cas=99705-65-4
eMolecules	27522677	https://orderbb.emolecules.com/search/#?query=27522677
eMolecules	300438312	https://orderbb.emolecules.com/search/#?query=300438312
eMolecules	85163569	https://orderbb.emolecules.com/search/#?query=85163569
eNovation Chemicals	D371708	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D371708&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-3540946390	https://mcule.com/MCULE-3540946390/
mcule	MCULE-8904227412	https://mcule.com/MCULE-8904227412/
MolPort	MolPort-006-395-323	https://www.molport.com/shop/molecule-link/MolPort-006-395-323
MuseChem	I012375	https://www.musechem.com/product/I012375.html
MuseChem	R008545	https://www.musechem.com/product/R008545.html
ShangHai Biochempartner	BCP000325	http://www.biochempartner.com/search_BCP000325
ShangHai Biochempartner	BCP02364	http://www.biochempartner.com/search_BCP02364

PubMed

Title	Date	PubMed
Exploring the relationship between social attachment and dopamine D2/3 receptor availability in the brains of healthy humans using [11C]-(+)-PHNO.	2017-04	26873034
Imaging dopamine D3 receptors in the human brain with positron emission tomography, [11C]PHNO, and a selective D3 receptor antagonist.	2010-08-15	20599188
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.	2005-06-16	15943487
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.	1993-10	7901395
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.	1991-10	1681090
D-2 agonists protect rodents against pilocarpine-induced convulsions by stimulating D-2 receptors in the striatum, but not in the substantia nigra.	1991-05	1924492
Differential effects of D1 and D2 agonists in MPTP-treated primates: functional implications for Parkinson's disease.	1990-06	2140595
MK 458, a selective and potent D2 receptor agonist in advanced Parkinson's disease.	1988-06	2900065
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.	1986-08-22	3758188

Sample Use Guides

In Vivo Use Guide

(up to 60 mg per day

Route of Administration: Oral

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:51:37 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:37 GMT 2025`
Record UNII	E5KFJ9796W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NAXAGOLIDE HYDROCHLORIDE

Official Name

English

L-647,339

Preferred Name

English

2H-NAPHTH(1,2-B)-1,4-OXAZIN-9-OL, 3,4,4A,5,6,10B-HEXAHYDRO-4-PROPYL-, HYDROCHLORIDE, (4AR-TRANS)-

Common Name

English

L-647339

Code

English

NAXAGOLIDE HYDROCHLORIDE [USAN]

Common Name

English

(+)-(4AR,10BR)-3,4,4A,5,6,10B-HEXAHYDRO-4-PROPYL-2H-NAPHTH(1,2-B)-1,4-OXAZIN-9-OL HYDROCHLORIDE

Common Name

English

NAXAGOLIDE HYDROCHLORIDE [MART.]

Common Name

English

MK-458

Code

English

NAXAGOLIDE HCL

Common Name

English

Code System Code Type Description

CAS

99705-65-4