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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 of RACLOPRIDE

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
12.7 nM [Ki]
13.4 nM [Ki]
3100.0 nM [Ki]
8.7 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Dopamine and glutamate release in the nucleus accumbens and ventral tegmental area of rat following lateral hypothalamic self-stimulation.
2001
Effects of the atypical neuroleptic clozapine on micturition parameters in anesthetized rats.
2001
Caudate nucleus dopamine D(2) receptors in depressed suicide victims.
2001
Scopolamine does not restore normal conditioned avoidance performance in raclopride-treated rats.
2001
Aging and caloric restriction in nonhuman primates: behavioral and in vivo brain imaging studies.
2001 Apr
D1 but not D2 dopamine receptor antagonism blocks the acquisition of a flavor preference conditioned by intragastric carbohydrate infusions.
2001 Apr
Expectation and dopamine release: mechanism of the placebo effect in Parkinson's disease.
2001 Aug 10
Functional neuroanatomy of the ventral striopallidal GABA pathway. New sites of intervention in the treatment of schizophrenia.
2001 Aug 15
Differential effects of dopamine antagonists on locomotor activity, conditioned activity and conditioned place preference induced by cocaine in rats.
2001 Dec
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
Neurons and neuronal systems involved in the pathophysiologies of Rett syndrome.
2001 Dec
Agonist, antagonist, and inverse agonist properties of antipsychotics at human recombinant 5-HT(1A) receptors expressed in HeLa cells.
2001 Dec 14
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
A PET study with [11-C]raclopride in Parkinson's disease: preliminary results on the effect of amantadine on the dopaminergic system.
2001 Feb
Delta 9-tetrahydrocannabinol-induced MAPK/ERK and Elk-1 activation in vivo depends on dopaminergic transmission.
2001 Jul
Atropine acts in the ventral striatum to reduce raclopride-induced catalepsy.
2001 Jul 27
The effect of dopamine receptor blockade on motor behavior in Aplysia californica.
2001 Jul-Aug
Iron deficiency decreases dopamine D1 and D2 receptors in rat brain.
2001 Jul-Aug
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
An investigation of the mechanisms responsible for acute fluoxetine-induced anxiogenic-like effects in mice.
2001 Jun
Vulnerability of positron emission tomography radiotracers to endogenous competition. New insights.
2001 Jun
[Th effect of D2-dopamine receptor blockade on glutamate release into extracellular space of Nucleus accumbens during food reinforcement].
2001 Mar-Apr
Pharmacodynamic modeling of oral levodopa in Parkinson's disease.
2001 Nov
Antagonism of the discriminative stimulus effects of cocaine at two training doses by dopamine D2-like receptor antagonists.
2001 Nov
Hypothermia reduces the rate of dissociation of specific ligands from dopamine-D2 and 5-hydroxytryptamine1A receptors in the mouse brain in vivo.
2001 Nov
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
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
Effects of raclopride in the nucleus accumbens on ethanol seeking and consumption.
2001 Oct
Apomorphine-induced changes in synaptic dopamine levels: positron emission tomography evidence for presynaptic inhibition.
2001 Oct
[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
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
Aberrant behavioral effects of a dopamine D1 receptor antagonist and agonist in monkeys: evidence of uncharted dopamine D1 receptor actions.
2001 Oct 1
Catecholamines in murine bone marrow derived mast cells.
2001 Oct 1
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
Drug-induced receptor occupancy: substantial differences in measurements made in vivo vs ex vivo.
2001 Sep
Expression and localization of human dopamine D2 and D4 receptor mRNA in the adrenal gland, aldosterone-producing adenoma, and pheochromocytoma.
2001 Sep
Imaging human mesolimbic dopamine transmission with positron emission tomography: I. Accuracy and precision of D(2) receptor parameter measurements in ventral striatum.
2001 Sep
Dopamine inhibits vasopressin action in the rat inner medullary collecting duct via alpha(2)-adrenoceptors.
2001 Sep
Positron emission tomography of dopamine pathways in familial Parkinsonian syndromes.
2001 Sep
A role for dopamine D1 receptors of the nucleus accumbens shell in conditioned taste aversion learning.
2001 Sep 1
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
Demonstration of competition between endogenous dopamine and [11C]raclopride binding in in vitro brain slices using a dynamic autoradiography technique.
2002 Apr
Clozapine can induce high dopamine D(2) receptor occupancy in vivo.
2002 Feb
SIC, an intracerebral beta(+)-range-sensitive probe for radiopharmacology investigations in small laboratory animals: binding studies with (11)C-raclopride.
2002 Feb
NMDA antagonist effects on striatal dopamine release: positron emission tomography studies in humans.
2002 Jan
Atropine reduces raclopride-induced muscle rigidity by acting in the ventral region of the striatum.
2002 Jan 11
Amphetamine-induced dopamine release and post-synaptic specific binding in patients with mild tardive dyskinesia.
2002 Mar
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
Relationship between blockade of dopamine transporters by oral methylphenidate and the increases in extracellular dopamine: therapeutic implications.
2002 Mar 1
Patents

Sample Use Guides

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
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
  • Download
Name Type Language
RACLOPRIDE
INN   MART.   WHO-DD  
INN  
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
Created by admin on Sat Jun 26 01:08:22 UTC 2021 , Edited by admin on Sat Jun 26 01:08:22 UTC 2021
Code System Code Type Description
CAS
84225-95-6
Created by admin on Sat Jun 26 01:08:22 UTC 2021 , Edited by admin on Sat Jun 26 01:08:22 UTC 2021
PRIMARY
EPA CompTox
84225-95-6
Created by admin on Sat Jun 26 01:08:22 UTC 2021 , Edited by admin on Sat Jun 26 01:08:22 UTC 2021
PRIMARY
EVMPD
SUB10239MIG
Created by admin on Sat Jun 26 01:08:22 UTC 2021 , Edited by admin on Sat Jun 26 01:08:22 UTC 2021
PRIMARY
FDA UNII
430K3SOZ7G
Created by admin on Sat Jun 26 01:08:22 UTC 2021 , Edited by admin on Sat Jun 26 01:08:22 UTC 2021
PRIMARY
NCI_THESAURUS
C152139
Created by admin on Sat Jun 26 01:08:22 UTC 2021 , Edited by admin on Sat Jun 26 01:08:22 UTC 2021
PRIMARY
PUBCHEM
3033769
Created by admin on Sat Jun 26 01:08:22 UTC 2021 , Edited by admin on Sat Jun 26 01:08:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL8809
Created by admin on Sat Jun 26 01:08:22 UTC 2021 , Edited by admin on Sat Jun 26 01:08:22 UTC 2021
PRIMARY
WIKIPEDIA
RACLOPRIDE
Created by admin on Sat Jun 26 01:08:22 UTC 2021 , Edited by admin on Sat Jun 26 01:08:22 UTC 2021
PRIMARY
MESH
D020891
Created by admin on Sat Jun 26 01:08:22 UTC 2021 , Edited by admin on Sat Jun 26 01:08:22 UTC 2021
PRIMARY
DRUG BANK
DB12518
Created by admin on Sat Jun 26 01:08:22 UTC 2021 , Edited by admin on Sat Jun 26 01:08:22 UTC 2021
PRIMARY
INN
5592
Created by admin on Sat Jun 26 01:08:22 UTC 2021 , Edited by admin on Sat Jun 26 01:08:22 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
LABELED -> NON-LABELED
Related Record Type Details
ACTIVE MOIETY