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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H20Cl2N2O3
Molecular Weight 347.237
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RACLOPRIDE

SMILES

CCN1CCC[C@H]1CNC(=O)C2=C(O)C(Cl)=CC(Cl)=C2OC

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 347.237
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 is a salicylamide neuroleptic, that acts as a selective antagonist of D2 dopamine receptors both in vitro and in vivo. Tritium-labelled raclopride has properties that demonstrate its usefulness as a radioligand for the labelling of dopamine-D2 receptors : 3H-Raclopride has a high affinity for the rat and human dopamine-D2 receptors, the non-specific binding of 3H-raclopride is very low, not exceeding 5% of the total binding and the distribution of the 3H-raclopride binding sites in the brain closely correlates with the dopaminergic innervation. The binding of 3H-raclopride is blocked by dopamine-D2 agonists and antagonists, while the D1 agonist SKF 38393 and the Dl antagonist SCH 23390 have much less potency. The interaction of dopamine with 3H-raclopride binding results in a shallow competition curve, which suggests that 3H-raclopride, similar to other dopamine-D2 radioligands, labels both high and low agonist affinity states of the dopamine-D2 receptor. The in vivo receptor binding studies performed with 3H-raclopride also demonstrate its favorable properties as a dopamine-D2 receptor marker in vivo In contrast to some other compounds used as radioligands, raclopride enters the brain readily and binds with a low component of non-specific binding in all dopamine-rich brain areas. A saturation curve may be achieved in vivo binding studies since injections of increasing concentrations of 3H-raclopride appears to be saturated at concentrations above 25 mkCi (corresponding to approximately 5 nmol/kg). Raclopride antagonizes apomorphine-induced hyperactivity in the rat at low doses (ED50 = 130 nM/kg i.p.) but induces catalepsy only at much higher doses (ED50 = 27 mkM/kg i.p.). Radiolabelled raclopride has been used as a ligand for in vitro and in vivo autoradiography in rat and primate brains. Raclopride C 11 is used with positron emission tomography (PET) as a clinical research tool to determine dopamine type 2 (D 2) receptor density in the human brain under normal and pathological conditions. For example, raclopride C 11 used in PET studies has served to confirm the age-related decrease in striatal dopamine D2 receptor density, which may be associated with a decline in the motor as well as cognitive functions. In patients with Alzheimer's disease, raclopride C 11 may be used to examine neuroreceptor distribution and quantities, which may help in the analysis of degenerative alterations of neuron populations and neuroreceptor systems in patients with this disease. In Huntington's disease, in which degeneration of neostriatal interneurons occurs (postsynaptic to the dopaminergic input), specific binding of raclopride C 11 to D 2 receptors may serve as one of the parameters in predicting performance in cognitive tasks.

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
RGS mRNA expression in rat striatum: modulation by dopamine receptors and effects of repeated amphetamine administration.
1999 Apr
Comparison of dopamine receptor antagonists on hyperlocomotion induced by cocaine, amphetamine, MK-801 and the dopamine D1 agonist C-APB in mice.
1999 Aug
Effects of SCH 23390, raclopride, and haloperidol on morphine withdrawal-induced aggression in male mice.
1999 Sep
Nonconserved residues in the second transmembrane-spanning domain of the D(4) dopamine receptor are molecular determinants of D(4)-selective pharmacology.
2000 Jan
Lack of specific effects of selective D(1) and D(2) dopamine antagonists vs. risperidone on morphine-induced hyperactivity.
2000 May
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
The role of D2-like dopamine receptors in the locomotor stimulant effects of cocaine in mice.
2001 Apr
An animal model of extrapyramidal side effects induced by antipsychotic drugs: relationship with D2 dopamine receptor occupancy.
2001 Apr
D2 dopamine receptor-G protein coupling. Cross-regulation of agonist and guanosine nucleotide binding sites.
2001 Apr 13
A simple method to measure baseline occupancy of neostriatal dopamine D2 receptors by dopamine in vivo in healthy subjects.
2001 Aug
Functional neuroanatomy of the ventral striopallidal GABA pathway. New sites of intervention in the treatment of schizophrenia.
2001 Aug 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
Increased dopamine d(2) receptor occupancy and elevated prolactin level associated with addition of haloperidol to clozapine.
2001 Feb
Negative interaction of dopamine D2 receptor antagonists and GBR 12909 and GBR 12935 dopamine uptake inhibitors in the nucleus accumbens.
2001 Feb 23
Receptor-mediated regulation of serotonin output in the rat dorsal raphe nucleus: effects of risperidone.
2001 Jan
Prepulse inhibition deficits and perseverative motor patterns in dopamine transporter knock-out mice: differential effects of D1 and D2 receptor antagonists.
2001 Jan 1
Therapeutic doses of oral methylphenidate significantly increase extracellular dopamine in the human brain.
2001 Jan 15
Delta 9-tetrahydrocannabinol-induced MAPK/ERK and Elk-1 activation in vivo depends on dopaminergic transmission.
2001 Jul
Additive hypothermic effects of the 5-HT1A receptor agonist 8-OH-DPAT and the dopamine D2/3 receptor agonist 7-OH-DPAT in the rat.
2001 Jul
A simple loop method for the automated preparation of (11C)raclopride from (11C)methyl triflate.
2001 Jul
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
No support for regional selectivity in clozapine-treated patients: a PET study with [(11)C]raclopride and [(11)C]FLB 457.
2001 Jun
Effects of dopamine antagonists with different receptor blockade profiles on morphine-induced place preference in male mice.
2001 Jun
Dopamine D2 receptor dimer formation: evidence from ligand binding.
2001 Jun 22
A strategy for removing the bias in the graphical analysis method.
2001 Mar
The imidazoline receptor ligand 2-(2-benzofuranyl)-2-imidazoline is a dopamine-releasing agent in the rat striatum in vivo.
2001 Mar 23
[Th effect of D2-dopamine receptor blockade on glutamate release into extracellular space of Nucleus accumbens during food reinforcement].
2001 Mar-Apr
Differential actions of dopamine receptor antagonism in rats upon food intake elicited by either mercaptoacetate or exposure to a palatable high-fat diet.
2001 May-Jun
Pharmacodynamic modeling of oral levodopa in Parkinson's disease.
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
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
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
Positron emission tomography of dopamine pathways in familial Parkinsonian syndromes.
2001 Sep
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
Amphetamine-induced dopamine release and post-synaptic specific binding in patients with mild tardive dyskinesia.
2002 Mar
Patents

Sample Use Guides

3.3 MBq/kg
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 Dec 16 04:51:27 GMT 2023
Edited
by admin
on Sat Dec 16 04:51:27 GMT 2023
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 Dec 16 04:51:27 GMT 2023 , Edited by admin on Sat Dec 16 04:51:27 GMT 2023
Code System Code Type Description
CAS
84225-95-6
Created by admin on Sat Dec 16 04:51:27 GMT 2023 , Edited by admin on Sat Dec 16 04:51:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID9045687
Created by admin on Sat Dec 16 04:51:27 GMT 2023 , Edited by admin on Sat Dec 16 04:51:27 GMT 2023
PRIMARY
EVMPD
SUB10239MIG
Created by admin on Sat Dec 16 04:51:27 GMT 2023 , Edited by admin on Sat Dec 16 04:51:27 GMT 2023
PRIMARY
FDA UNII
430K3SOZ7G
Created by admin on Sat Dec 16 04:51:27 GMT 2023 , Edited by admin on Sat Dec 16 04:51:27 GMT 2023
PRIMARY
NCI_THESAURUS
C152139
Created by admin on Sat Dec 16 04:51:27 GMT 2023 , Edited by admin on Sat Dec 16 04:51:27 GMT 2023
PRIMARY
PUBCHEM
3033769
Created by admin on Sat Dec 16 04:51:27 GMT 2023 , Edited by admin on Sat Dec 16 04:51:27 GMT 2023
PRIMARY
ChEMBL
CHEMBL8809
Created by admin on Sat Dec 16 04:51:27 GMT 2023 , Edited by admin on Sat Dec 16 04:51:27 GMT 2023
PRIMARY
WIKIPEDIA
RACLOPRIDE
Created by admin on Sat Dec 16 04:51:27 GMT 2023 , Edited by admin on Sat Dec 16 04:51:27 GMT 2023
PRIMARY
MESH
D020891
Created by admin on Sat Dec 16 04:51:27 GMT 2023 , Edited by admin on Sat Dec 16 04:51:27 GMT 2023
PRIMARY
DRUG BANK
DB12518
Created by admin on Sat Dec 16 04:51:27 GMT 2023 , Edited by admin on Sat Dec 16 04:51:27 GMT 2023
PRIMARY
SMS_ID
100000080289
Created by admin on Sat Dec 16 04:51:27 GMT 2023 , Edited by admin on Sat Dec 16 04:51:27 GMT 2023
PRIMARY
INN
5592
Created by admin on Sat Dec 16 04:51:27 GMT 2023 , Edited by admin on Sat Dec 16 04:51:27 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Ki
LABELED -> NON-LABELED
TARGET -> INHIBITOR
Ki
Related Record Type Details
ACTIVE MOIETY