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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H20Cl2N2O3.C4H6O6
Molecular Weight 497.324
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RACLOPRIDE TARTRATE

SMILES

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

InChI

InChIKey=QULBVRZTKPQGCR-NDAAPVSOSA-N
InChI=1S/C15H20Cl2N2O3.C4H6O6/c1-3-19-6-4-5-9(19)8-18-15(21)12-13(20)10(16)7-11(17)14(12)22-2;5-1(3(7)8)2(6)4(9)10/h7,9,20H,3-6,8H2,1-2H3,(H,18,21);1-2,5-6H,(H,7,8)(H,9,10)/t9-;1-,2-/m01/s1

HIDE SMILES / InChI

Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Stereoselective binding of 11C-raclopride in living human brain--a search for extrastriatal central D2-dopamine receptors by PET.
1988
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
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
Decreased striatal dopamine efflux after intrastriatal application of benzazepine-class D1 agonists is not mediated via dopamine receptors.
2001 Apr
Rewarding properties of methylphenidate: sensitization by prior exposure to the drug and effects of dopamine D1- and D2-receptor antagonists.
2001 Aug
A simple method to measure baseline occupancy of neostriatal dopamine D2 receptors by dopamine in vivo in healthy subjects.
2001 Aug
Effect of endogenous dopamine on extrastriatal [¹¹C]FLB 457 binding measured by PET.
2001 Aug
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
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
Decline in motor functions in aging is related to the loss of NMDA receptors.
2001 Jul 13
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
No support for regional selectivity in clozapine-treated patients: a PET study with [(11)C]raclopride and [(11)C]FLB 457.
2001 Jun
Dopamine receptor antagonists prevent the d-amphetamine-induced increase in calcitonin gene-related peptide levels in ventral striatum.
2001 Jun 15
Dopaminergic retinal cell differentiation in culture: modulation by forskolin and dopamine.
2001 May
Dopamine-dependent inhibition of glycine release in the nucleus accumbens of the rat brain during food consumption.
2001 May-Jun
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
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
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
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

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 Fri Dec 15 15:33:50 GMT 2023
Edited
by admin
on Fri Dec 15 15:33:50 GMT 2023
Record UNII
EXZ5FGZ55J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RACLOPRIDE TARTRATE
Common Name English
BENZAMIDE, 3,5-DICHLORO-N-(((2S)-1-ETHYL-2-PYRROLIDINYL)METHYL)-2-HYDROXY-6-METHOXY-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
EXZ5FGZ55J
Created by admin on Fri Dec 15 15:33:50 GMT 2023 , Edited by admin on Fri Dec 15 15:33:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID00913404
Created by admin on Fri Dec 15 15:33:50 GMT 2023 , Edited by admin on Fri Dec 15 15:33:50 GMT 2023
PRIMARY
PUBCHEM
57346
Created by admin on Fri Dec 15 15:33:50 GMT 2023 , Edited by admin on Fri Dec 15 15:33:50 GMT 2023
PRIMARY
CAS
98185-20-7
Created by admin on Fri Dec 15 15:33:50 GMT 2023 , Edited by admin on Fri Dec 15 15:33:50 GMT 2023
PRIMARY
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ACTIVE MOIETY