RACLOPRIDE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H20Cl2N2O3
Molecular Weight	347.2373
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN1CCC[C@@]1([H])CN=C(c2c(c(cc(c2OC)Cl)Cl)O)O

InChI

InChIKey=WAOQONBSWFLFPE-VIFPVBQESA-N

InChI=1S/C15H20Cl2N2O3/c1-3-19-6-4-5-9(19)8-18-15(21)12-13(20)10(16)7-11(17)14(12)22-2/h7,9,20H,3-6,8H2,1-2H3,(H,18,21)/t9-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C15H20Cl2N2O3
Molecular Weight	347.2373
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2975809https://www.ncbi.nlm.nih.gov/pubmed/3131792 | https://www.ncbi.nlm.nih.gov/pubmed/3873656 | https://www.ncbi.nlm.nih.gov/pubmed/27286237 | https://www.ncbi.nlm.nih.gov/pubmed/21678422
Curator's Comment:: the description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24848155 | https://www.ncbi.nlm.nih.gov/pubmed/17765546 | https://www.drugs.com/mmx/raclopride-c-11.html

Raclopride C-11 is radiolabeled substituted benzamides, that acts as a selective antagonist on D2 dopamine receptors and used for visualization of dopamine receptor binding in the human brain by positron emission tomography (PET). PET with 11C-raclopride provides a widely validated method for assessing baseline levels of dopamine (DA) type 2 receptor (DA2R) availability as well as DA2R occupancy induced by either pharmacological or nonpharmacological stimuli. 11C-raclopride-PET can be used in the research of numerous facets of human behavior and cognition in health and in disease.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 283 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24848155	Antagonist 2575	12.7 nM [Ki]
Dopamine D3 receptor 85 Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24848155	Antagonist 2575	13.4 nM [Ki]
Dopamine D4 receptor 66 Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17765546	Antagonist 2575	3100.0 nM [Ki]
Dopamine receptor 58 Target ID: CHEMBL2096905 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2391685	Antagonist 2575	8.7 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 261 Sources: https://www.drugs.com/mmx/raclopride-c-11.html	Diagnostic	Approved 8043	Unknown Approved Use Unknown
Huntington's disease 24 Sources: https://www.drugs.com/mmx/raclopride-c-11.html	Diagnostic	Approved 8043	Unknown Approved Use Unknown
Parkinson's disease 219 Sources: https://www.drugs.com/mmx/raclopride-c-11.html	Diagnostic	Approved 8043	Unknown Approved Use Unknown
Depression 215 Sources: https://clinicaltrials.gov/ct2/show/NCT00832221	Diagnostic	Phase I 409	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effects of single and repeated administration of 1,2,3,4-tetrahydroisoquinoline analogs on the binding of [11C]raclopride to dopamine D2 receptors in the mouse brain.	2001	11725814
Dopamine and glutamate release in the nucleus accumbens and ventral tegmental area of rat following lateral hypothalamic self-stimulation.	2001	11720786
Effects of the atypical neuroleptic clozapine on micturition parameters in anesthetized rats.	2001	11574938
Caudate nucleus dopamine D(2) receptors in depressed suicide victims.	2001	11490173
Scopolamine does not restore normal conditioned avoidance performance in raclopride-treated rats.	2001	11475009
Aging and caloric restriction in nonhuman primates: behavioral and in vivo brain imaging studies.	2001 Apr	11795523
D1 but not D2 dopamine receptor antagonism blocks the acquisition of a flavor preference conditioned by intragastric carbohydrate infusions.	2001 Apr	11526968
Expectation and dopamine release: mechanism of the placebo effect in Parkinson's disease.	2001 Aug 10	11498597
Functional neuroanatomy of the ventral striopallidal GABA pathway. New sites of intervention in the treatment of schizophrenia.	2001 Aug 15	11489297
Differential effects of dopamine antagonists on locomotor activity, conditioned activity and conditioned place preference induced by cocaine in rats.	2001 Dec	11856897
Combined alpha 2-adrenergic/D2 dopamine receptor blockade fails to reproduce the ability of clozapine to reverse phencyclidine-induced deficits in prepulse inhibition of startle.	2001 Dec	11797077
Neurons and neuronal systems involved in the pathophysiologies of Rett syndrome.	2001 Dec	11738851
Agonist, antagonist, and inverse agonist properties of antipsychotics at human recombinant 5-HT(1A) receptors expressed in HeLa cells.	2001 Dec 14	11755134
Facilitation of dopaminergic neural transmission does not affect [(11)C]SCH23390 binding to the striatal D(1) dopamine receptors, but the facilitation enhances phosphodiesterase type-IV activity through D(1) receptors: PET studies in the conscious monkey brain.	2001 Dec 15	11746724
A PET study with [11-C]raclopride in Parkinson's disease: preliminary results on the effect of amantadine on the dopaminergic system.	2001 Feb	11487182
Delta 9-tetrahydrocannabinol-induced MAPK/ERK and Elk-1 activation in vivo depends on dopaminergic transmission.	2001 Jul	11553284
Atropine acts in the ventral striatum to reduce raclopride-induced catalepsy.	2001 Jul 27	11672560
The effect of dopamine receptor blockade on motor behavior in Aplysia californica.	2001 Jul-Aug	11509200
Iron deficiency decreases dopamine D1 and D2 receptors in rat brain.	2001 Jul-Aug	11509198
D1 or D2 antagonism in nucleus accumbens core or dorsomedial shell suppresses lever pressing for food but leads to compensatory increases in chow consumption.	2001 Jul-Aug	11509194
An investigation of the mechanisms responsible for acute fluoxetine-induced anxiogenic-like effects in mice.	2001 Jun	11485052
Vulnerability of positron emission tomography radiotracers to endogenous competition. New insights.	2001 Jun	11476162
[Th effect of D2-dopamine receptor blockade on glutamate release into extracellular space of Nucleus accumbens during food reinforcement].	2001 Mar-Apr	11548610
Pharmacodynamic modeling of oral levodopa in Parkinson's disease.	2001 Nov	11706980
Antagonism of the discriminative stimulus effects of cocaine at two training doses by dopamine D2-like receptor antagonists.	2001 Nov	11702088
Hypothermia reduces the rate of dissociation of specific ligands from dopamine-D2 and 5-hydroxytryptamine1A receptors in the mouse brain in vivo.	2001 Nov	11692232
Dopamine D2 receptor-mediated G-protein activation in rat striatum: functional autoradiography and influence of unilateral 6-hydroxydopamine lesions of the substantia nigra.	2001 Nov 30	11716810
Catalepsy induced by a blockade of dopamine D1 or D2 receptors was reversed by a concomitant blockade of adenosine A(2A) receptors in the caudate-putamen of rats.	2001 Oct	11703457
Effects of raclopride in the nucleus accumbens on ethanol seeking and consumption.	2001 Oct	11696662
Apomorphine-induced changes in synaptic dopamine levels: positron emission tomography evidence for presynaptic inhibition.	2001 Oct	11598492
[11C]Raclopride binding was reduced in vivo by sigma(1) receptor ligand SA4503 in the mouse brain, while [11C]SA4503 binding was not by raclopride.	2001 Oct	11578899
Potentials and pitfalls using high affinity radioligands in PET and SPET determinations on regional drug induced D2 receptor occupancy--a simulation study based on experimental data.	2001 Oct	11554812
Aberrant behavioral effects of a dopamine D1 receptor antagonist and agonist in monkeys: evidence of uncharted dopamine D1 receptor actions.	2001 Oct 1	11600103
Catecholamines in murine bone marrow derived mast cells.	2001 Oct 1	11585626
Potent inhibitory effect of selective D2 and D3 agonists on dopamine-responsive dorsomedial arcuate neurons in brain slices of estrogen-primed rats.	2001 Oct 19	11712668
Drug-induced receptor occupancy: substantial differences in measurements made in vivo vs ex vivo.	2001 Sep	11594441
Expression and localization of human dopamine D2 and D4 receptor mRNA in the adrenal gland, aldosterone-producing adenoma, and pheochromocytoma.	2001 Sep	11549694
Imaging human mesolimbic dopamine transmission with positron emission tomography: I. Accuracy and precision of D(2) receptor parameter measurements in ventral striatum.	2001 Sep	11524609
Dopamine inhibits vasopressin action in the rat inner medullary collecting duct via alpha(2)-adrenoceptors.	2001 Sep	11504796
Positron emission tomography of dopamine pathways in familial Parkinsonian syndromes.	2001 Sep	11472880
A role for dopamine D1 receptors of the nucleus accumbens shell in conditioned taste aversion learning.	2001 Sep 1	11517277
Age-related changes of dopamine D1-like and D2-like receptor binding in the F344/N rat striatum revealed by positron emission tomography and in vitro receptor autoradiography.	2001 Sep 15	11494399
Demonstration of competition between endogenous dopamine and [11C]raclopride binding in in vitro brain slices using a dynamic autoradiography technique.	2002 Apr	11842445
Clozapine can induce high dopamine D(2) receptor occupancy in vivo.	2002 Feb	11862380
SIC, an intracerebral beta(+)-range-sensitive probe for radiopharmacology investigations in small laboratory animals: binding studies with (11)C-raclopride.	2002 Feb	11850489
NMDA antagonist effects on striatal dopamine release: positron emission tomography studies in humans.	2002 Jan	11746730
Atropine reduces raclopride-induced muscle rigidity by acting in the ventral region of the striatum.	2002 Jan 11	11779574
Amphetamine-induced dopamine release and post-synaptic specific binding in patients with mild tardive dyskinesia.	2002 Mar	11850144
In vivo assessment of adenoviral vector-mediated gene expression of dopamine D(2) receptors in the rat striatum by positron emission tomography.	2002 Mar 1	11793425
Relationship between blockade of dopamine transporters by oral methylphenidate and the increases in extracellular dopamine: therapeutic implications.	2002 Mar 1	11793423

Patents

Sample Use Guides

In Vivo Use Guide

Intravenous, 110 to 496 MBq (3 to 13.4 millicuries), with specific radioactivity between 18.5 and 55.5 MBq (0.5 and 1.5 millicuries), administered as a bolus injection

Route of Administration: Intravenous

In Vitro Use Guide

Primary cultures of rat neonatal ventricular cardiac myocytes were prepared by enzymatic digestion of ventricle tissue with 0.25% trypsin. The cardiomyocytes were first plated for 2 h to reduce non-myocyte contamination. The cells were then washed to remove erythrocytes, replated at a density of 2.0x10^6 cells in culture flasks and incubated at 37C in the presence of 5% CO2 in a humidified incubator. 2.0x10^6 neonatal rat ventricular myocytes were treated with 40 mkM of Raclopride for 24 h.

Substance Class	Chemical Created by `admin` on `Sat Jun 26 01:08:22 UTC 2021` Edited by `admin` on `Sat Jun 26 01:08:22 UTC 2021`
Record UNII	430K3SOZ7G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RACLOPRIDE

Official Name

English

(S)-3,5-DICHLORO-N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-2-HYDROXY-6-METHOXYBENZAMIDE

Systematic Name

English

(S)-3,5-DICHLORO-N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-6-HYDROXY-O-ANISAMIDE

Common Name

English

RACLOPRIDE [INN]

Common Name

English

RACLOPRIDE [MART.]

Common Name

English

RACLOPRIDE [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66883